Jill Filipovic NOV. 24, 2017

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Jill Filipovic is the author of “The H Spot: The Feminist Pursuit of Happiness” and a contributing opinion writer.

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WEST CHESTER, Ohio—He swings the golf club like a right-hander, which he is, but putts as a southpaw. Maybe it’s a metaphor for a conservative politician who often turned to liberals in crunch time, but I’m too busy losing $20 on this hole to appreciate it. We’re on the green now, surveying his 10-foot par attempt, a modest breeze transporting his tobacco cologne. With a posture as unique as his personality—back hunched over nearly parallel to the turf, left shoulder dipped well below the right, fingers interlocked around a grip of blue rubber—he gazes downward and shuffles his feet. The veins are still dancing in his muscular, leathery legs as the blade retreats from the ball, and it’s apparent within moments of their reunion that something isn’t right. As the Titleist Pro V1 finds its resting place, several feet shy and slightly west of its final destination, he can’t mask his frustration. “Nice one, Boner,” he mutters.

To play golf with John Boehner is to learn there are unwritten rules governing the use of the word Boner. When spoken by his close friends—“Thatta boy, Boner!”—it’s almost always to congratulate him on a good shot. When the former U.S. House speaker uses it—“Aww, Jee-sus, Boner!”—it’s almost always to rebuke himself for a bad one. Today he is saying it with ruinous frequency.

Story Continued Below

We’re on Boehner’s home course, the Wetherington Golf and Country Club, on a Monday afternoon in early June. Tucked away in West Chester, Ohio—an affluent enclave of suburban Cincinnati, part of his old district—the club is hosting a charity fundraiser, dubbed the “Boehner Classic,” benefiting a nearby Boys & Girls Club. The former speaker is one of two star attractions; the other is his friend, the professional golfer Fuzzy Zoeller, a character known more for his off-color jokes than his two major championships. With wealthy donors ponying up to play alongside them—but some of his old buddies also in town—Boehner decides to form a group of nine players, myself and Zoeller included, and creates a team scramble that pits five golfers against the other four.

But something isn’t right with the former speaker’s game. Long considered one of Washington’s finest golfers, he is spraying shots left and right with choppy, self-doubting swings. Sensing my surprise, Boehner says his handicap has skyrocketed since leaving Congress two years ago. After he misses that 10-foot putt, and we climb into our cart, I ask why. “You have to concentrate while you hit the ball,” he tells me. “That’s my biggest problem in golf these days. I just can’t concentrate. I could always concentrate on what I had to do. But these days … ” Boehner pauses for several seconds, then pulls hard on the Camel 99 wedged between his knuckles. “I just can’t concentrate.”

***

To outsiders, Boehner might just be the happiest man alive, a liberated retiree who spends his days swirling merlot and cackling at Speaker Paul Ryan’s misfortune. The truth is more complicated. At 67, Boehner is liberated—to say what he spent many years trying not to say; to smoke his two packs a day without undue stress; to chuckle at the latest crisis in Washington and whisper to himself those three magic words: “Not my problem.” And yet he is struggling—with the lingering perception that he was run out of Congress; with his alarm about the country’s future; and with the question of what he’s supposed to do next. After leaving office, Boehner says a longtime family friend approached him. “You’ve always had a purpose—your business, your family, politics,” the friend said. “What’s your purpose now?” Boehner says the question gnaws at him every day.

We met three times over the summer, his most candid and revealing series of interviews since a third attempted coup on his speakership led him to say to hell with it and retire early. The first interview was in June at Wetherington; the second in July at Burning Tree Club, a private, all-male establishment in Bethesda, Maryland; the third in September following a joint fundraiser with Ryan at the Bengals vs. Packers game in Green Bay, Wisconsin. In the whole of our conversations, he asked only five or six times for something to remain off the record. In those instances, I agreed. Everything else was fair game—and he did not disappoint. From his text messages with George W. Bush, to his scathing critiques of conservative media and his former antagonists on Capitol Hill, to his disgust at America’s being stuck with a choice between Donald Trump and Hillary Clinton, the former speaker held little back.

What I discovered from 18 hours on the record with him, and dozens more with his friends, is that for all the talk of Boehner living the dream in retirement—mowing and manicuring his lawn, fiddling around at his workbench, spending time with his grandson—he is lacking a certain peace. It’s the type of tranquility that accompanies the knowledge that your life’s work won’t be remembered as a failure; that the party and the institution you gave everything to aren’t collapsing because of mistakes you might have made.

Boehner is a fascinating and paradoxical figure in his own right. He was the brilliant salesman who couldn’t get his own members to buy. The back-slapping creature of K Street who never took a single earmark. The gruff chain-smoker who weeps at the mere mention of schoolchildren. The Midwestern everyman who won’t be seen in public without a clean shave and an ironed shirt. The bartender’s son who became speaker of the House.

But the story of Boehner’s 25 years in Washington is also the story of the Republican Party, the Congress and American politics in the post-Ronald Reagan era: an account of corruption and crusading, enormous promises and underwhelming results, growing ideological polarization and declining faith in government. The same centrifugal forces that made Boehner’s job impossible have bedeviled his successor, Ryan, and kept the GOP majorities in Congress from passing any landmark legislation in 2017. Now, as the revolutionary fervor that swept Boehner into the speakership degenerates into a fratricidal conflict centered around Trump, the former speaker’s frontline view of the Republican civil war is essential to understanding what went wrong.

***

On the eve of his golf outing, I find myself on Boehner’s back patio. He’s hosting a barbecue for friends who came to Ohio for the fundraiser, and we get acquainted as Boehner works several outdoor grills, Camel in his left hand and tongs in his right. Among others seated around the table, sipping Maker’s Mark 46 from blue plastic cups and smoking cigars, are Dick, who owns a winter home near Boehner’s on Florida’s Marco Island; Ed, who also spends winters on Marco Island but still runs a business out of western Ohio; and Mick, the longtime chief of staff in Boehner’s personal office who lives nearby. All three promise that I’m in for a treat. They aren’t lying: Boehner has prepared a feast of teriyaki-marinated flank steaks, his specialty; chunks of seared beef tenderloin; grilled chicken breasts; a salad of avocado, tomatoes and fresh mozzarella; au gratin potatoes; a sweet corn skillet; and baked crescent rolls. As we eat, someone jokes that the only thing missing are hot dogs. Boehner looks up from his plate. “I’ve never had a hot dog for dinner in my life,” he says, stone-faced.

After we eat, Boehner sits across from me, reaches for a lighter and indicates he’s ready to talk. Boehner smokes two packs a day and has a habit of pinching off the smoldering end of his cigarette, rolling the butt into a ball and shoving it into his pocket. (On the back nine a day later, Boehner stops at a receptacle and scoops from his pocket some two dozen smoke-stained balls.) Of his 11 siblings, one has passed away. It was lung cancer. Boehner says this doesn’t concern him—“If I was going to die from smoking cigarettes, I’d already be dead”—but I notice that his laughs, which come often and easy, are almost always accompanied by coughs. Ah-heh. Ah-heh.

Breaking the ice, I mention some news of the day—that Trey Gowdy appears likely to become chairman of the House Oversight and Government Reform Committee. The previous chairman, Jason Chaffetz, had abruptly announced his resignation from Congress; House conservatives had hoped that Jim Jordan, a senior member on the committee, might pursue the chairmanship. Boehner grins. “Gowdy—that’s my guy, even though he doesn’t know how to dress,” he says. Then Boehner leans back in his chair. “Fuck Jordan. Fuck Chaffetz. They’re both assholes.”

And away we go.

Boehner’s beef with Chaffetz, who would later join Fox News as a paid contributor, is not personal—just that he’s a “total phony” who possessed legislative talent but focused mostly on self-promotion. “With Chaffetz,” Boehner says, “it’s always about Chaffetz.”

His problems with Jordan, the founding chairman of the ultraconservative House Freedom Caucus, run much deeper. To Boehner and his allies, Jordan was the antagonist in the story of his speakership—an embodiment of the brinkmanship and betrayal that roiled the House Republican majority and made Boehner’s life miserable. Although he would tell me in later conversations that he holds no grudges against anyone, today Boehner unloads on his fellow Ohioan. “Jordan was a terrorist as a legislator going back to his days in the Ohio House and Senate,” Boehner says. “A terrorist. A legislative terrorist.”

If he sounds exasperated, it’s because this is the central irony of his career: A quarter-century before the conservative insurgency stormed Washington and derailed his speakership, John Boehner was the conservative insurgency.

***

ACT I

Boehner’s pursuit of national office was his first rebellion against the establishment.

When the news broke in 1989 that Ohio Congressman Donald “Buz” Lukens, a Republican, had paid a 16-year-old for sex—and was trying to get her mother a government job—the party bosses tried pushing him out. Lukens wouldn’t budge. So they coalesced around a challenger: former GOP Congressman Tom Kindness, who had held the seat prior to Lukens. Months went by before Boehner, a state representative who had made himself wealthy selling corrugated boxes and injection-molded plastics, jumped into the race—much to the displeasure of party leaders. Boehner didn’t have insider connections or family favors to cash in; one of a dozen kids who grew up in a two-bedroom home and cleaned floors in his father’s shot-and-a-beer saloon, he worked as a janitor to pay for college and first took elected office as a township trustee before later winning a statehouse seat.

Armed with little name recognition and even less support, Boehner poured his own money into the race—nearly emptying his family’s bank account by spending $150,000 on the campaign. “It was too much money,” Debbie Boehner, his wife, tells me. Her husband nods. “I put it all on the line.” Money wasn’t Boehner’s problem; it was his name. Almost everyone in the district pronounced it Boner. “Think about this,” Mick tells me on the patio, laughing so hard he can barely finish. “You had a guy named Kindness running against a guy named Boner.” Defying expectations, Boehner won the primary and gained the party’s support. That included help from Paul Ryan, a local college Republican who volunteered that fall. “I didn’t know him,” Ryan says. “I thought his name was Boner.”

By then, the Democrats’ post-Watergate zeal for reform had long since faded, and the House was widely seen as the oozing center of the Washington swamp—an out-of-control legislative slum that invited malfeasance and vice. It was against this backdrop that Boehner, a newcomer, made it his mission to clean up Congress. “He indicated he wanted to be very aggressive and very much involved in reform efforts, and he brought a lot of energy to it,” Newt Gingrich, who was then the second-ranking House Republican, remembers of the freshman lawmaker.

Almost from the day he arrived on Capitol Hill in January 1991, Boehner found himself arguing with employees of the House Bank—a financial institution for members of Congress only—who explained that his paycheck could be deposited only with them. These rules vexed the rookie legislator. Months later, he spotted a statistic from the Government Accountability Office audit of the House Bank: more than 8,000 of its checks had bounced. “They needed all of us to keep our money in those accounts so they could have a big enough float to keep the bank alive,” Boehner recalls. After discussing this realization with six of his fellow freshman Republicans, they agreed to expose the rot. As they did so, in the form of a privileged resolution, Boehner tells me, Speaker Tom Foley and Majority Leader Dick Gephardt—both Democrats—approached him on the House floor, as did Bob Michel, the Republican minority leader. “All three of them said essentially the same thing,” Boehner remembers. “‘We didn’t do anything wrong, and we won’t do it again.’” As Boehner and Co. dug deeper, probing the bank’s finances and pushing for the disclosure of members whose accounts were overdrawn, they earned a nickname: the Gang of Seven. Less than a year into his first term, as Americans seethed over the improprieties exposed by these freshman renegades—with Democrats, the majority party, shouldering the blame—the House Bank was closed. And Boehner’s star was born.

The Gang’s work wasn’t finished. Over the next several years they turned their attention to other targets, including the scandal-plagued House Post Office, leading to the indictment and imprisonment of House Ways and Means Committee Chairman Dan Rostenkowski, a powerful Illinois Democrat. Sensing an opportunity to seize Washington’s moral high ground and win back the House after 40 years in the minority—President Bill Clinton’s own troubles would be icing on the cake—Gingrich enlisted Boehner to help draft the “Contract with America,” a list of promises to voters.

As he helped guide the party’s midterm strategy, Boehner’s high-profile role made him a hero to reform-minded conservatives seeking office across the country in part of what would later be dubbed the “Republican Revolution” of 1994. Richard Burr, who today is the senior senator from North Carolina, was campaigning for a House seat that year and remembers hearing about Boehner. “I think John was probably the first one that actually intended to drain the swamp. He was a radical,” Burr says. “The closest example would be a Freedom Caucus guy today.” Jordan, running his first race for the statehouse that year, recalls fawning over his future nemesis. “Here’s a guy who’s fighting to clean things up in Washington.”

Republicans won the majority, and Boehner, leveraging his newfound celebrity, ran for the No. 4 spot in House leadership: conference chairman. Gingrich had become speaker with Michel’s retirement, and he had a different person in mind for conference chair. But Boehner won anyway, cashing in on favors he had accumulated by virtue of his status as a prodigious young fundraiser.

At freshman orientation following the 1994 midterms, Boehner, now a four-year veteran of the House, sat with three incoming members—Burr, Saxby Chambliss of Georgia and Tom Latham of Iowa—and discovered they had much in common. The four would become inseparable. “There’s a very small cadre of things that makes John Boehner like you,” Burr says. “We all liked red wine. At the time most of us used tobacco products. … John had his, let’s say, peculiarities about him. He was not shy to be critical of one’s hair or one’s dress if in fact he found it to be outside of what he perceived to be appropriate or the norm. And I think we were the only three people that were willing to put up with his crap. So, we became his best friends.”

Boehner’s fastidiousness would become legendary among colleagues. Friends say he would iron virtually every piece of clothing—shirts, undershirts, boxer shorts, pants, suit jackets, ties. Patrick McHenry, currently the chief deputy whip, recalls how, on his first day in Congress in 2005, Boehner walked into the cloakroom and spotted him eating an ice cream sandwich. They had never met. Boehner lit a cigarette and scowled at him. “Don’t do that,” he said, pointing to the frozen snack. “Why?” McHenry replied. “You’re gonna be a fatass,” Boehner told him.

This is Boehner’s way of showing affection; after he calls me “shithead” for the umpteenth time on the golf course, his buddy Dick leans over. “You know that means he likes you, right?” (His buddies have the same towel-snapping style. At one point, I hit a low, screaming drive. “You know what your problem is?” Fuzzy Zoeller asks me. “L.O.F.T.” I nod, saying I should tee my ball higher. “No,” he shakes his head. “Lack of fucking talent.” Boehner howls with approval.)

Having watched Gingrich stalk the halls of Congress, rarely making eye contact with colleagues—much less greeting them—Boehner knew he needed to engage members while still being himself. “You grow up in a bar and you learn to mix it up with people,” Boehner says. “It was a way of building relationships, as goofy as it sounds. And if you’ve got a relationship with people, you’ve got a chance to move them.”

Those relationships failed to save him from what looked like a political death sentence.

***

The year 1994 didn’t just usher in new leadership to the House and the GOP; it marked a profound shift in Washington’s partisan relations. Gingrich, a master messenger with a zero-sum approach to ideological warfare, perfected the art of launching poll-tested attacks on Democrats as “radicals” who threatened liberty. With a penchant for turning personal disagreement into political Armageddon, Gingrich weaponized the speakership as never before.

“The beginning of the scorched-earth policy really began with Gingrich winning in the mid-’90s, the Gingrich revolution, and the enormous pressure put on moderate Republicans to walk away from anything remotely approaching a compromise,” says former Vice President Joe Biden, who was then a senator from Delaware.

Another change, one that would later inform some of the opposition to Boehner’s speakership, was the consolidation of power at the expense of committee chairmen and rank-and-file members. “Gingrich basically created a process where the speaker was the epicenter of the House,” says Joshua Huder, a senior fellow at Georgetown University’s Government Affairs Institute.

As the fourth-ranking House Republican—behind Gingrich, Majority Leader Dick Armey and Majority Whip Tom DeLay—Boehner could see the toll these institutional transformations took on GOP members, who felt disempowered by Gingrich’s imperial style. After Clinton won reelection in 1996, Republicans grew restless. The GOP had suffered terribly from Gingrich’s handling of a lengthy government shutdown from December 1995 to January 1996—a lesson that informed Boehner’s aversion to such tactics years later—as well as his constant public feuding and a barrage of ethics charges against him. In January 1997, Gingrich became the first speaker ever reprimanded for an ethics violation.

That summer, several members of the extended Republican leadership huddled to discuss a coup against Gingrich; when the speaker learned of their plotting, they scrambled to protect themselves and Gingrich remained in power. It has long been considered fact that Boehner and Armey joined this mutiny. But Boehner insists he was never involved. He claims that DeLay and Republican leadership chairman Bill Paxon were the masterminds, both eyeing promotions, and that “when it all blew up, they dragged me and Armey into it with them.” He sighs. “DeLay and I were never close. Matter of fact, half the stab wounds in my back are from him.” The one person who believed Boehner’s story was Gingrich. “John is a very honest guy. He’ll be honest with you negatively and he’ll be honest with you positively,” Gingrich says. “I never doubted him.”

Whatever role Boehner played, the damage was done. Gingrich stepped down after Republicans lost five seats in the 1998 midterms, and when heir apparent Bob Livingston shockingly announced that he would decline the speakership—amid swirling reports of extramarital shenanigans—Dennis Hastert, the chief deputy whip, became speaker. Armey and DeLay kept their posts. But there was blood in the water, and Boehner became “the sacrificial lamb,” Chambliss says, losing his job as conference chair to J.C. Watts of Oklahoma.

“Most people thought I was going to leave,” Boehner says of his humiliating defeat. Instead, he recalls telling his then-chief of staff, Barry Jackson, as they left the vote: “I’m never going to let ’em see me sweat. They’re never going to see an ounce of disappointment on my face. We’re just going to earn our way back.”

***

Two years later—on the heels of George W. Bush’s 2000 election—the chairmanship of the House Education and the Workforce Committee opened up, and Boehner saw his chance. Roy Blunt, a Missourian and the chief deputy whip, remembers Boehner’s presentation to the Steering Committee: He brought metal lunchboxes personalized with members’ names, and folded up inside were his education policy papers. Boehner lacked seniority, but “it was the right thing to do to bring him back into a more active role in the House,” Blunt recalls.

The timing was serendipitous: Bush wanted to show the American people that Washington was still functioning after the September 11 terrorist attacks, and signing a major, bipartisan overhaul of education would be just the thing. Boehner, a golfing buddy of the president’s, found himself paired with Ted Kennedy, the liberal lion of the Senate, crafting the most ambitious K-12 bill in American history. “Ted Kennedy was a great compromiser. Everybody thought he was rigid, just wanted his way. That is not Ted Kennedy,” says Harry Reid, who then served as Senate majority whip. “And for Boehner, Ted was perfect, because he was always willing to do a deal.”

The result, No Child Left Behind, was the linchpin to Boehner’s political reclamation project—even though the federal government’s intrusion into state and local education policymaking spawned a conservative backlash still felt today. Boehner blames “the implementation” of the bill, but makes no apology for breaking with party orthodoxy in writing it. Passage of NCLB might have been the genesis of the right’s caricature of Boehner as a spineless centrist, but it also cemented his reputation as an effective dealmaker. “To some members that probably defined him as more moderate than they would like,” Blunt says. “To others it defined him as a guy with capacity to get hard things done.”

By 2006, the party was reeling—two prolonged wars, ballooning deficit, skyrocketing debt—and Democrats were threatening to take back the House. DeLay had been promoted to majority leader, and Blunt to majority whip; both men loomed as obstacles for Boehner’s designs on climbing back into the leadership. But DeLay’s indictment in late 2005 opened the door. His resignation sparked an intense five-month period of jockeying for the role of majority leader: Boehner, Blunt and John Shadegg, chairman of the conservative Republican Study Committee, all wanted the job. Blunt tallied 110 votes on the first ballot, shy of the majority he needed; ahead of the second ballot, Paul Ryan, a member of Shadegg’s operation, informed Boehner’s team that they would throw their votes to him. The comeback was complete: Boehner was elected House majority leader in what he describes as the best day he ever had in Congress.

Boehner had made the leadership election a referendum on the GOP’s ethical lapses—fittingly but ironically, considering he was bludgeoned in 1995 for distributing Big Tobacco’s campaign checks on the House floor. Having apologized and pushed to ban that very practice, Boehner preserved his reputation as a reformer and was now working to fulfill a campaign promise nobody thought he could keep: banning earmarks.

The funding of pet projects in lawmakers’ districts helped leadership to keep members in line, but fueled a culture of venality and waste; boondoggles like the “Bridge to Nowhere,” a 2005 project calling for a $223 million earmark to construct a bridge to a remote, sparsely populated Alaska island, became symbols of congressional excess. Boehner never accepted an earmark in Congress—and he enjoyed railing against those who did. His heckling once provoked Don Young, an Alaskan himself, to pin Boehner against a wall inside the House chamber and hold a 10-inch knife to his throat. Boehner says he stared Young in the eyes and said, “Fuck you.” (Young says this account is “mostly true,” but notes that the two became good friends, with Boehner later serving as his best man.)

Boehner made good on his promise. He rolled the powerful Appropriations Committee and rid the House of earmarks, claiming a watershed victory for good government. History will judge it as perhaps Boehner’s most significant achievement—and one that made running the House all the more difficult.

***

ACT II

He wasn’t majority leader for long.

With public opinion turning sharply against Bush—his handling of the Iraq War, Hurricane Katrina and the economy, specifically the early stages of the housing bubble—Democrats took advantage of a demoralized Republican base and won back the House in 2006, picking up 31 seats and handing Nancy Pelosi the speaker’s gavel. It wasn’t all bad for Boehner: Hastert’s retirement cleared the way for him to become the top House Republican.

Although nobody knew at the time, Hastert would become another in a long string of prominent congressional Republicans to be disgraced by scandal. In 2015, Hastert reached a plea agreement with federal prosecutors, acknowledging that he had delivered hush money to one of several male former high school students he had sexually abused. The Boehners, like others who knew him, were dumbfounded. “Denny Hastert was the nicest guy,” Debbie says. “But you know what? His wife never came to D.C.” Did they ever notice anything unusual, I ask? “Only his staff,” Boehner tells me. “He had more gay staff than anybody I knew—at a time when it was a bit unusual.” He pauses. “OK, fine. I didn’t care. But when all this stuff broke a couple years ago, it took my breath away.”

Now minority leader, Boehner spent much of 2008 corralling difficult votes to prop up a sinking economy and an unpopular, lame-duck president. Jordan, who arrived in the class of 2006, remembers watching during his freshman term as the leader straddled a line between his inner conservatism and his loyalty to the president and the party. This reached a memorable climax in late September 2008, when two-thirds of the House GOP voted against a bailout package requested by Bush and Treasury Secretary Hank Paulson—sending global markets tumbling and Boehner scrambling to find votes. A revised bill passed four days later, averting catastrophe, but the uprising had officially begun.

Republicans, having spent and borrowed extravagantly during the Bush years—and expanded the reach of the federal government with No Child Left Behind, the Medicare Part D prescription drug benefit, and the bailouts—now faced a conservative backlash. Pivoting sharply, GOP lawmakers greeted the election of Barack Obama in 2008 with unified opposition to his stimulus package. This brought accusations of hypocrisy. “People thought we had spent too much. Thought the tax cuts were too much,” Boehner says. “OK, fine—we need to look ahead. We’ve got a spending problem.”

With Democrats controlling the White House and both chambers of Congress in 2009 and 2010, Boehner felt obligated to hold the line and galvanize the party faithful who had failed to mobilize behind Senator John McCain, the centrist-leaning 2008 nominee. He led the charge against the stimulus, the Affordable Care Act, Dodd-Frank financial regulation, and cap and trade, and his leadership was unquestioned in the GOP conference; Boehner’s fiery floor speech denouncing the ACA shortly before its passage was his high-water mark among colleagues. “Look at how this bill was written,” the minority leader said on the House floor in March 2010. “Can you say it was done openly?” Republicans and Democrats shouted in response. “With transparency and accountability?” The shouts continued. “Without backroom deals struck behind closed doors, hidden from the people? Hell no, you can’t!”

Out in the provinces, however, the party was transforming, with implications that would prove fateful for Boehner: Rallies nationwide featured Paul Revere imitators waving “Don’t Tread on Me” flags, and candidates for Congress were aligning with the so-called Tea Party in denouncing both Obama’s overreach and the excesses of the previous GOP administration in equally strident terms. They promised to come to Washington as a new breed of Republican—revolutionaries promising ideological purity rather than partisan achievement. “It was very appealing in running for Congress to say that you would never settle for less than 100 percent,” recalls Blunt, who left the House and won a Senate seat in 2010.

The uprising put Boehner in a predicament as Republicans stampeded back into the House majority that November, flipping 63 Democrat-held seats. The new speaker had campaigned on a generic but effective message—“Where are the jobs?”—that revealed a traditional sensibility about how to oppose the president. Boehner wanted Obama gone, but he wasn’t much for stunts and gamesmanship; his goal was to prove in 2011 and 2012 that Republicans could be trusted once again as a responsible governing party, thus aiding Obama’s defeat in 2012.

“When I saw that Boehner was becoming speaker, I thought that was a positive thing,” Biden tells me. “I thought there could be actually some work together, some collaboration together, and we could actually get some things done. But I thought, most of all, he was going to treat the president with more respect than some of his colleagues had.”

The class of 2010 wasn’t interested in collaboration. These rowdy freshmen lawmakers saw Boehner’s “Hell no” speech as a blueprint for their slash-and-burn strategy. When they realized after arriving in D.C. that he would not lead accordingly, dozens of them gravitated toward someone who would: Jordan, the newly installed chairman of the Republican Study Committee. When I ask about those factions forming in 2011, Jordan cites the “Hell no” speech and shrugs. “That’s the John Boehner we were hoping for.”

***

The Republican Party’s incipient civil war moved quickly from the campaign trail to Capitol Hill. The fundamentally irreconcilable approaches of Boehner and Jordan, and the members who followed them, produced an increasingly volatile series of intraparty collisions during the new GOP majority’s first term in 2011 and 2012.

Some of this owed to Boehner’s not taking the campaign rhetoric of his new colleagues at face value. “These were people who ran against Washington and planned on voting that way,” explains Tim Huelskamp, who was elected in the 2010 wave and then lost his Kansas district’s Republican primary in 2016. Boehner rejects the notion that he was ill-prepared to deal with these rookie legislators, but his allies concede there was a blind spot. “He thought of himself as someone who was of the Tea Party mentality before the Tea Party was a thing … so I think there were some assumptions made that he got these people, and that they would see he was one of them,” says Anne Bradbury, Boehner’s former floor director. “But that really never came together.”

Some of the freshmen took one look at Boehner—the golf-tanned back-slapper who wore handsome, tailored suits and rented his D.C. apartment from a registered lobbyist—and saw the embodiment of everything they were sent to destroy. “They never gave him a fair shake,” says Kevin McCarthy, the California congressman who was then Boehner’s majority whip.

One thing everybody agrees on: The debt-ceiling negotiations that summer of 2011 marked the beginning of the end of Boehner’s speakership.

Facing an August deadline to raise the nation’s borrowing limit, which gave conservatives occasion to take a symbolic stand against fiscal irresponsibility, the speaker appeased his members by declaring that every new dollar of debt must be offset by commensurate spending cuts. The speaker hoped this “Boehner Rule” would project strength from his young, untested conference, but it backfired: Conservatives repeatedly balked at potential compromises being discussed by Boehner and Obama, believing they had leverage to hold out for a better deal.

They rallied around a plan called Cut, Cap and Balance, which required a hike in the debt ceiling to be accompanied by a cut in federal spending, a cap on future levels of spending and an amendment to the Constitution requiring Congress to balance its budget. The proposal, which Boehner privately derided as “Snap, Crackle and Pop,” passed the House in mid-July but was rejected out of hand by Obama and the Reid-run Senate. Boehner, staring down the August deadline, moved on; conservatives were irate that leadership had caved. “It was the most popular Republican vote we had taken,” Huelskamp says. “And 18 hours later he caved to Obama on some stupid deal and we all went home dejected for the August recess.”

Jordan and Senator Jim DeMint of South Carolina, who helped craft the Cut, Cap and Balance legislation, urged the GOP leadership in both chambers to force the issue—to “fight,” as conservatives loved to say, and let the public decide which party was right. To Boehner, this was a futile strategy—Democrats controlled the White House and the Senate, leaving him with few cards to play. But the debt-ceiling mess was only a taste of things to come—DeMint would later haunt Boehner as president of The Heritage Foundation, whose lobbying arm, Heritage Action, pressured GOP lawmakers into defying the speaker at every turn. “He ran Heritage into the ground,” Boehner told me after DeMint was fired this summer. “Heritage was a respected conservative think tank, and he turned it into some half-assed political operation.”

The rising influence of Heritage and other “outside groups” on the right—Club for Growth, FreedomWorks, Tea Party Patriots—made the speaker’s job infinitely harder. Egged on by an angry GOP base, they repeatedly cornered Republicans into fights they couldn’t possibly win. The defining implosion of their first year in the majority came in late July when it was revealed that Jordan’s staff had been conspiring with outside groups to pressure RSC members—Jordan’s own members—to vote against Boehner’s debt deal. It was a stunning breach of decorum and a confirmation of what Obama had already figured out: that Boehner wasn’t dealing from a place of strength. Jordan apologized profusely to the conference, but it was too late. Whatever trust once existed between the warring GOP factions had vanished, never to return—and it destroyed Boehner’s credibility with Democrats.

“He could practically never deliver his votes,” Pelosi tells me. When I ask Boehner about this, during a rain delay at Wetherington, he smirks. “It’s hard to negotiate when you’re standing there naked,” he says. “It’s hard to negotiate with no dick.”

***

It didn’t help that Boehner spent part of that summer negotiating the biggest deal in modern political history—and keeping his members entirely in the dark about it.

Boehner’s conservative foes criticized him as cautious at best and gutless at worst, but he is better understood as a calculated gambler. For instance, he greenlit Ryan’s controversial, safety-net-slashing budget proposals at a time when many party leaders were running away from them, because he felt voters would reward the GOP for taking a stand on entitlement spending. The speaker wasn’t afraid of going big. But the circumstances had to be right. And in June 2011, they were.

What began as a bipartisan photo-op—18 holes at the Andrews Air Force Base course with Obama and Boehner teaming against Biden and Ohio Governor John Kasich—ended with a suggestion from Boehner that the debt-ceiling predicament actually gave them the chance for a once-in-a-lifetime deal to address America’s longer-term crisis: the retirement of the baby boomer generation and the strain it placed on the country’s finances. Republicans might agree to increased revenue via eliminating tax deductions and loopholes (violating conservative orthodoxy) if Democrats could agree to spending cuts and entitlement reforms (violating liberal orthodoxy). Obama signaled his openness to the idea, and for the next five weeks their teams worked in secret to hammer out a compromise, knowing that fury awaited in their respective bases.

On Sunday, July 17, it appeared they had a deal. Boehner and Virginia Representative Eric Cantor—whom the speaker had reluctantly brought into the negotiations, knowing the majority leader’s distrust of Obama could poison the talks—worked out some final details that morning at the White House. When the president returned from church, Boehner says, he invited them both into the Oval Office and shook their hands. Some fine-tuning remained, but in Boehner’s mind the so-called grand bargain was done. The framework included reforms to Medicare, Medicaid and Social Security; $1.2 trillion in cuts to discretionary spending; and $800 billion in new revenue. “I was one happy son of a bitch,” Boehner tells me.

The next 48 hours changed everything. On Tuesday morning, the so-called Gang of Six—three senators from each party who had been discussing their own sweeping fiscal agreement—announced a briefing for their colleagues at the Capitol. They unveiled a separate framework, totally unaware of what Obama and Boehner had agreed to. This deal included significantly more revenue. Chambliss, by then a senator, was one of the GOP Gang members and had no idea—because Boehner had been negotiating with the president in private—that their announcement would kill the speaker’s deal with the White House. Obama saw that Republican senators were endorsing a deal that included far more revenue, and knew there was no way he could sell the grand bargain to his liberal base. When he came back with a counteroffer, seeking a higher revenue number, it validated Cantor’s warnings about not trusting the president. And by that point Boehner’s members had heard enough about the grand bargain to know they didn’t like it—with the $800 billion revenue figure, much less something higher.

So the deal fell apart, and the two sides peddled their competing versions of events: Boehner’s team said the White House moved the goal posts, while Obama’s allies said the speaker couldn’t sell his own members on the deal. “The White House tried to spin this a million different ways,” Boehner tells me. “But we had a deal. They walked away from it.” When I ask Biden about this, he takes a long pause. “I think they had a genuine misunderstanding,” he says. “I think John is completely sincere, but … we had this Rubik’s cube we were constantly struggling with as to whether or not what was being sold by John in the House was going to be able to be delivered, and what was being sold in the Senate was able to be delivered.”

Harry Reid insists his caucus would have provided enough votes for passage, despite deep reservations among Democrats. And he says to this day he blames the Gang of Six for scuttling the grand bargain by releasing a framework that had no chance of becoming law. “They may get mad at me now, I don’t care. I knew it would never work,” Reid says of the Senate proposal. “It was a doomed failure. I told them that. So, I was hoping Boehner and Obama would move forward.”

There is truth in both arguments: that Obama walked away and Boehner couldn’t convince his people. That said, knowing how his career ended, Boehner counts the grand bargain as his “biggest disappointment”—not only because the national debt just blew past $20 trillion, with no hope of entitlement fixes on the horizon, but also because at least there would be something big to show for the heartburn he endured as speaker. “If I could have pulled this deal off, they could have thrown me out the next day,” Boehner says. “I would have been the happiest guy in the world.”

***

Having lost the faith of the White House as an effective partner, and the confidence of his right flank to do its bidding, Boehner approached the remainder of the term warily in hopes of avoiding self-inflicted wounds that would hurt GOP presidential nominee Mitt Romney’s chances of defeating Obama. Instead, after the president won reelection, Boehner was soon back at the negotiating table dealing with yet another crisis. This time, it was the so-called fiscal cliff, in which the expiration of the Bush-era tax cuts and harsh, automatic spending cuts agreed to in 2011 (following the grand bargain’s collapse) would take effect simultaneously in 2013—risking to send the country back into recession.

Obama had campaigned in 2012 on the proposal that tax rates should jump for individuals making more than $200,000 annually. After weeks of haggling following his victory, the president offered a concession: $400,000 for individuals. Boehner made a counteroffer of $1 million. Had the entire House GOP rallied behind that idea, they might have forced Obama’s number higher. But a larger number of Republicans, having pledged to an outside group never to raise taxes, period, refused to go along. A dejected Boehner conceded defeat in a private conference meeting, and, in a remarkable moment of vulnerability, recited the Serenity Prayer used in 12-step addiction programs.

Boehner was running out of patience. The day before, Reid had blasted him from the Senate floor, saying he ran the House like a dictator. “I don’t do angry. Nobody on my staff has ever seen me angry,” Boehner tells me. “But that little son of a bitch got under my skin.” When he arrived at the White House for a meeting with the president and congressional leaders, Boehner spotted Reid talking with Senate Minority Leader Mitch McConnell. “I walked right up to him and said, ‘Harry, you can go fuck yourself. You ever listen to that shit that comes out of your mouth?’” Boehner imitates a flustered Reid, then adds: “I thought McConnell was going to have a heart attack.”

(Reid adds an interesting detail. “Then he said, ‘We’ve got to get along better,’” Reid recalls, grinning. “That’s one reason I like him. He’s not a phony. … He wanted me to know that he wanted us to get along. So that was his way of telling me.” Boehner agrees; he says they became “really good friends” after the incident, and today construction is underway on a new think tank at the University of Nevada Las Vegas, which they will co-chair. Boehner visited in August and Reid tells me they went sightseeing together like an old married couple; he even put down the car window so Boehner could smoke as they drove.)

The fiscal cliff further diminished Boehner’s standing on the right. When the new Congress convened in January 2013, some two dozen House conservatives plotted to overthrow him. Any speaker needs a majority of votes cast on the House floor on the first day of a new Congress; Huelskamp and others concluded that if 17 Republicans voted against Boehner, that would force a second ballot—and he would step aside out of shame. Huelskamp says the coup participants “signed their names in blood” the night before the vote—not literally—and he was stunned the next day to see just 12 of them follow through. Boehner survived, but was embarrassed by the revolt. It was the first attempt on his speakership, though not the last.

The resentment toward Boehner was rooted in many grievances, some more legitimate than others. Without question, he ran the House in a top-down fashion inherited from Gingrich, centralizing the policymaking process in leadership offices and spurning input from back-bench members. He would also anger conservatives by allowing deadlines to creep up, refusing to state the conference’s strategy because he knew they would disapprove—and then he would jam them at the last minute. There also was outrage at his punitive tactics. In late 2012, he had kicked Huelskamp and several other conservatives off key committees as punishment for their votes against leadership initiatives. It was predictable: The earmark ban had robbed Boehner of his best tool to incentivize on-the-fence members, leaving him to lead with all sticks and few carrots. With outside groups actively recruiting primary challengers, members in red districts often saw no political upside in voting with the leadership—a dynamic Boehner could not counter.

Things improved somewhat after the 2013 speaker vote, when Boehner privately assembled a group of five House conservatives—Ryan, Jordan, Tom Price, Jeb Hensarling and Steve Scalise—to discuss a cease-fire. This temporarily ended the hostilities. But by summer, Republicans were engaged in another brutal internecine conflict—this time over immigration.

A bipartisan group of eight senators had crafted a comprehensive immigration bill that appeared to have support in the House GOP. But in June, when the Senate passed it—68 to 32, with 14 Republicans voting yes—House members found themselves under siege from constituents and conservative groups. The fatal flaw: It provided a path to citizenship, albeit a winding one, for people in the country illegally. Many conservatives could support a path to legal status but not citizenship; Democrats, on the other hand, essentially took a citizenship-or-nothing approach. Boehner was boxed in: He wanted immigration reform, and personally didn’t mind citizenship—especially for minors brought to the U.S. unwittingly. But putting the bill on the floor meant it might pass into law with perhaps as few as 40 or 50 of his members voting yes. Conservatives would never forgive him for overruling the vast majority of his membership. Looking back, Boehner says not solving immigration is his second-biggest regret, and he blames Obama for “setting the field on fire.” But the former speaker doesn’t mention the nativist voices in his own party that came to dominate the debate, foreshadowing the presidential campaign three years later. Ultimately, the speaker’s immigration quandary boiled down to a choice between protecting his right flank and doing what he thought was right for the country—and Boehner chose the former.

It wasn’t the only time. That summer, conservatives were also getting an earful about the Obamacare exchanges opening on October 1. House Republicans had voted repeatedly to repeal the law but the Senate refused to act, and their constituents, justifiably, wanted to know why Obamacare still existed when they had been promised otherwise. “Somehow, out on the campaign trail, the representation was made that you could beat President Obama into submission to sign a repeal of the law with his name on it,” Cantor says. “And that’s where things got, I think, disconnected from reality.” (In Ohio, listening to his pals groan about Obamacare, Boehner explains why his former colleagues haven’t repealed it: “Their gonads shriveled up when they learned this vote was for real.”)

Republicans’ penchant for overpromising and underdelivering would ultimately enable the ascent of Donald Trump, who positioned himself as a results-oriented outsider who would deliver where politicians had failed. In the shorter term, it invited something less dramatic: a government shutdown. Eager to demonstrate that all options were being exhausted to defeat Obamacare, Ted Cruz in the Senate and conservatives in the House concocted a plan: Because the government needed new funding on October 1, the same day the exchanges would open, they would propose funding the rest of the federal government—while defunding Obamacare.

Boehner objected. Not only would Democrats never go for it; Republicans would be blamed for the resulting government shutdown. “I told them, ‘Don’t do this. It’s crazy. The president, the vice president, Reid, Pelosi, they’re all sitting there with the biggest shit-eating grins on their faces that you’ve ever seen, because they can’t believe we’re this fucking stupid.’” (Boehner, at one point, surprises me by saying he’s proud of Cruz—whom he once called “Lucifer in the flesh”—for acting responsibly in 2017. Do you feel badly about calling him Lucifer, I ask? “No!” Boehner snorts. “He’s the most miserable son of a bitch I’ve ever had to work with.”)

After railing against the defund strategy, however, Boehner surveyed his conference and realized it was a fight many members wanted—and some needed. Yielding, he joined them in the trenches, abandoning his obligations of governance in hopes of strengthening his standing in the party. But the 17-day shutdown proved costly. Watching as Republicans got butchered in nationwide polling, the speaker finally called a meeting to inform members that they would vote to reopen the government and raise the debt ceiling. “I get a standing ovation,” Boehner says. “I’m thinking, ‘This place is irrational.’”

***

By spring 2014 it appeared Boehner’s days were numbered. A bigger bloc of members—not all of them troublemakers—told me at the time they would vote him out at the end of the year, replacing him with a new speaker for the next Congress. What they didn’t know is that Boehner had already decided to step down, having instructed his three most trusted staffers to lay out his options for retiring at the end of 2014.

In a digital-time-stamped memo written in November 2013, titled “The End,” those staffers—chief of staff Mike Sommers, deputy chief of staff Dave Schnittger and personal office chief of staff Mick Krieger—presented Boehner with three choices. “Option 1” meant announcing in January 2014 his plan to leave at the end of the year. “Option 2” meant announcing that plan in August. “Option 3” meant announcing it in November, after the midterm elections.

Boehner ruled out Option 1, deciding that yearlong leadership races would invite further discord and make legislating hopeless. But he never had the chance to decide between Options 2 and 3. That’s because on June 10, 2014, as Boehner dined at Alberto’s, his favorite Capitol Hill ristorante, Sommers called him with stunning news. Cantor—his majority leader and heir apparent—had lost his primary in Virginia’s 7th District to a little-known challenger whose campaign was boosted by Tea Party groups and right-wing radio hosts. “I was pissed,” Boehner tells me. “Because in my mind, I was done.” (“That was the worst campaign ever run,” Boehner adds of Cantor’s defeat. “I never saw anything like it.”)

Boehner’s next call was to Ryan, asking him to become majority leader and slide into the speakership the following year. “He called me that night and said, ‘You’ve got to do this job,’” Ryan tells me. “And I was like, ‘There’s no way I’m doing this job. You’ve got to stay.’” Boehner consulted with friends and determined there was only one course of action. “I remember telling him, ‘You don’t have a choice. This conference falls apart if you leave now,’” Chambliss says.

Cantor’s loss triggered a leadership shuffle: McCarthy was promoted to majority leader, and Scalise was elected whip. The new chief deputy whip, McHenry—who admits to being “a bomb-thrower” his first three years in Congress and viewing Boehner as a nincompoop—tells me his view changed upon joining the speaker at his daily management meetings. “I’m in there and it’s this realization—Oh, wait a second. Boehner does actually care about policy. He understands the dynamics of the conference. He understands where all these different groups are.” He laughs. “Like, who is this guy?” McHenry wishes other conservatives had his vantage point. “He could see through opportunities without having to make the 50 or 75 phone calls that I made.”

On the golf course in Ohio, Boehner singles out McHenry as an example of how some lawmakers mature after initially acting like “anarchists.” He also makes a prediction: “McHenry’s going to be the speaker one day.”

***

Republicans took back the Senate in 2014 but little changed. If anything, conservative voters grew angrier at the lack of results. “There were a lot of no-win situations,” Scalise says. “You go and pick fights with the Senate, but in the end, they’ve got a totally different set of rules that made it hard for any of our reforms even to get to the president’s desk.” McCarthy adds, “I remember telling Mitch McConnell one time, ‘Your rules are gonna get the speaker thrown out.’”

Boehner was unenthused about returning in 2015. Convinced that he was taking one for the team by staying, he was more anxious than anyone had ever seen him in January, when conservatives organized a second mutiny on the floor. “He was puffing cigarettes faster than usual, and that’s hard to do,” says Chambliss, who sat with Boehner during the speakership vote. “It obviously worked out. But from then on, I think it was only a matter of time for John to make the decision that this wasn’t worth it.”

Wounded by that January uprising, and seeing no light at the end of the tunnel—Jordan that same month had co-founded a new group, the House Freedom Caucus, designed to push leadership even harder than the Republican Study Committee had—Boehner plotted a new exit strategy. He would announce his retirement on his birthday, November 17.

But Boehner’s plans were thwarted once again. Mark Meadows, another co-founder of the Freedom Caucus, sent shock waves through Congress on his birthday—July 28—by filing a “motion to vacate.” The idea was to force another floor vote on the speakership, gambling that this time Boehner would either lose or step down to avoid the spectacle.

When news broke of Meadows’ move, Boehner’s allies were furious. They implored him to call up the motion and hold the vote immediately, in a show of strength. Boehner wanted to think. And after meeting the next day with Jordan and four other Freedom Caucus members, the speaker decided against it. They had urged him not to hold the vote before August recess, since the Republicans who supported him would then spend the month getting pummeled back home. Boehner found himself agreeing. “He’s like, ‘I don’t want to make members take that vote,’” Ryan, who urged a same-day vote, recalls Boehner telling him. “Totally selfless. Always thinking about protecting the membership.”

To be clear: Boehner was never going to lose the speakership. In another internal memo—this one digital-time-stamped September 16, 2015, and titled “Save the Institution”—Sommers explained to Boehner that his survival would be ensured if Pelosi had Democratic members vote “present” when the motion came up. If they did, Boehner could win with a simple majority of Republican votes cast—which was never in doubt, as the number of GOP defectors was between 20 and 40. In a subsequent meeting, Boehner broached the idea with Pelosi and she agreed. “You can’t have 30 people in your caucus decide they’re going to vacate the chair,” she tells me. “He knew I had—not his back, but the institution’s back.”

And yet the maneuver didn’t sit well with Boehner—especially since he was dead set on leaving in November anyway. “It would be awful for the institution. We hadn’t gone through this in 100 years,” he says. “All these Republicans were going to get crap at home for supporting me, only to have me leave soon after that.” Boehner is still angry with Meadows, who canceled an interview for this article, for putting him in that position: “He’s an idiot. I can’t tell you what makes him tick.”

On September 24, Pope Francis addressed Congress—a visit Boehner had worked for years to secure—and he says everything clicked. “I never saw members happier than they were the day the pope was there. Democrats, Republicans, House, Senate. Everybody was happy.”

In his D.C. apartment that night, Boehner told his wife what he was thinking of announcing. “And then I went to bed and slept eight hours. Like a baby. It was unbelievable.” The next morning, after his customary breakfast at Pete’s Diner, “I looked at that statue of the Virgin Mary next to St. Peter’s Church, and I decided, all right, today’s the day,” Boehner recalls. “And as soon as I decided that, I thought, you know, the press is going to think I got forced out of here. I just want them to understand there’s not one moment of trepidation in this. So, I’m going to walk out there singing ‘Zip-a-dee-do-dah.’ I made those decisions at the same moment.”

Boehner was not forced out—at least, not in any technical or parliamentary sense. And there is no question he felt unburdened by the decision to finally throw in the towel. But the singing routine betrayed the fact that he was hardly his normal, cheerful self in those final months. “He was just kind of emotionally done,” says Bradbury, his former aide. “The fact that he felt like he’d given and given to the conference and the country, and this is how he was rewarded, when he didn’t want to be there anyway—” she stops herself. “It was very disheartening for him.”

***

ACT III

“Nothing good happens after 10 p.m.”

These are words Boehner lived by throughout his career. In a capital city where booze flows freely and parties run late and lawmakers live away from spouses, he decided long ago it would behoove him to be in bed by 10 o’clock. This also allowed him to rise early, take his long walk for coffee, wolf down some eggs at his favorite greasy spoon and read the newspapers before work. Retirement has meant adjustments—Boehner makes his own breakfast and spends his days dialing into conference calls, giving paid speeches or doing housework—but one constant remains: asleep by 10. On my first night in Ohio, just as the conversations were getting loose and the cocktails were getting stiff, Boehner informed the patio crowd he was turning in. It was 9:45.

But the next night was different. After the golf outing, and a reception in the clubhouse, Boehner hopped in his customized golf cart—a retirement gift from his congressional colleagues—and zipped across three moonlit fairways and into his driveway. I figured it was time to say goodnight. But Boehner invited me in for a nightcap. What followed, over bottomless glasses of wine, can only be described as Boehner unshackled. On several occasions, Debbie warned him to stop telling me things; when he ignored her, she would put a couch cushion over my recording device. The highlight was Boehner telling me a story about George W. Bush—and prefacing it by saying, “I shouldn’t tell you this.” Debbie, opening a bottle of red in the kitchen, barked: “Then don’t!”

Boehner leans back in his favorite recliner, retrieving a glowing cigarette from its ashtray. “So I get a text from 43 about a month ago, maybe six weeks ago.” Boehner’s close friend Ed, who joined our nightcap, interjects: “Off the record?” Boehner waves him off: “It doesn’t matter.” He lets out a thick cough, smoke escaping his mouth, and continues. “So 43 says, ‘Hey, are you talking to Ryan? Are you giving him advice?’ I said, ‘Yeah, if he calls I give him advice.’” Boehner takes a long, satisfied drag. “And he texts me back: ‘He needs to call you more.’”

Boehner erupts into a long, uncontrollable cough-laugh. It is 10:40 p.m.

The anecdote underscores how Boehner and Bush are “two peas in the same pod,” as the former speaker says, a pair of even-keeled gents who tried to ignore the stresses of their respective jobs and who enjoy commiserating now that they are both retired. (Boehner tells me that when Bush, while in office, refused to join Burning Tree—due to the optics of a president golfing someplace women aren’t allowed—he told the commander in chief, “You’re a pussy.” Years later, when Bush became a member after leaving the White House, Boehner says he told Bush: “You’re still a pussy.”)

But the story also speaks to a concern for Boehner these days: the well-being of his successor. Ryan never wanted the job; it took Boehner more than a year to convince him, and there were drastic measures involved. When McCarthy abruptly decided he would not run for speaker, everyone knew Ryan was the only unifying choice. And Boehner knew which buttons to push: The speaker called Cardinal Timothy Dolan, archbishop of New York and president of the United States Conference of Catholic Bishops, asking him to pressure Ryan. Dolan obliged, phoning the congressman and piling on more of the “Catholic guilt” Boehner had employed.

It worked, of course. But it’s clear Boehner feels a little guilt himself. Ryan now holds the thankless job he was desperate to escape, and finds himself buffeted by the same internal forces. “And then there’s the White House,” Boehner tells me, rolling his eyes. “Dysfunction is a relative term. Right now it looks like I was a genius.”

Even before Trump was elected, Boehner was back in the Capitol one day and visited the speaker’s office. Ryan, he says, looked at him wearily: “This job is a lot harder than I thought.” When I ask Ryan about this, he confirms the story and laughs. “And I wanted to say, ‘You ass, you stuck me with this sh—’” He stops himself. But it’s been a tough day, and the speaker needs to vent. “Just getting people to agree on how to do things that are in their own interest is hard to do. Getting people to agree, getting to consensus, on things that are basic and axiomatic, is really hard to do,” Ryan tells me. “You need more of a degree in psychology than you need in economics.” (Ryan has, however, found comfort in torturing Boehner: The speaker inherited his predecessor’s security detail, and whereas Boehner demanded they be freshly shaven every day, Ryan let them grow unruly beards—pictures of which are often texted to their former boss, code name “Tan Man.”)

The Freedom Caucus has begun to squeeze Ryan, much as it did to Boehner—warning him that without changes his tenure could be similarly endangered. And Ryan, as Boehner did, is telling friends that he’s losing patience with the job. When I tell Jordan about Boehner’s description of him—“a legislative terrorist”—and ask about whether he’s holding the speakership hostage, he flashes surprise and eventually irritation. “Oh, my goodness. I feel sorry for the guy if he’s that bitter about a guy coming here and doing what he told the voters he was gonna do. Wow. I feel bad for him,” Jordan says. “But in the end, we were not doing what the voters elected us to do and what we told them we were going to do. We just weren’t. And I would argue the same thing is happening now.”

Jordan’s veiled threat only partially explains the frustration written all over Ryan’s face when we meet: Earlier that day, after Ryan scoffed at a Democratic proposal to pass a short-term extension of the debt ceiling, Trump met with Pelosi and Democratic Senate leader Chuck Schumer and gave them exactly what they wanted. “Um, yeah, that one—yeah, that’s kind of par for the course these days,” Ryan tells me, his tie loosened and a sense of resignation in his voice. “This is a presidency that offers some surprises.” Weeks later, when I ask Boehner about Trump’s deal with the Democrats, he erupts into a cough-laugh. “My guess is that he thought he was doing everybody a favor. He had no idea he was cutting off McConnell and Ryan’s legs.”

Trump himself is less a source of apprehension for top Republicans than what he represents: a fracturing of the party and a corollary decline in its ability to govern. “We basically run a coalition government without the efficiency of a parliamentary system,” Ryan complains.

When I ask Boehner whether the Republican Party can survive this, he cuts me off. “There is no Rep—.” He stops himself. “You were about to say, ‘There is no Republican Party,” I tell him. He shrugs. “There is. But what does it even mean? Donald Trump’s not a Republican. He’s not a Democrat. He’s a populist. He doesn’t have an ideological bone in his body.” So who, I ask, is the leader of the party? “There is nobody,” he says.

I ask Boehner what he thinks historians will make of his speakership. “They’ll be talking about the end of the two-party system,” he replies.

***

In our months of conversations, Trump was the lone subject about which Boehner seemed reluctant to speak freely. Timing was partly to blame: Weeks before I came to Ohio, Boehner in a paid speech had described Trump’s presidency as “a complete disaster.” It brought angry voicemails from then-chief of staff Reince Priebus, who carried stern words from Trump himself. “The White House isn’t real happy with me right now,” Boehner said at the time. His caution faded somewhat as summer wore on. When I saw him six weeks later at Burning Tree—fresh off a blockbuster report that Donald Trump Jr. had met with a Russian government official during the campaign in hopes of gaining compromising information on Hillary Clinton—Boehner greeted me in the parking lot with a knowing grin. Before I said anything, he shook his head and muttered, “What a shit show.” But our most interesting exchange came in Green Bay, after a hearty meat-and-potato breakfast, when I raised the matter of this summer’s march in Charlottesville, and Trump’s equivocations. “I do not believe that he is a racist. I do not believe that he is a white supremacist,” Boehner tells me. “He has clearly done some things to lead people who never liked him to say those things about him.” So, I ask, how can Trump fix that? Boehner arches an eyebrow. “Is it fixable?”

Boehner worries about the deepening fissures in American society. But he sees Trump as more of a symptom than the cause of what is a longer arc of social and ideological alienation, fueled by talk radio and Fox News on the right and MSNBC and social media on the left. “People thought in ’09, ’10, ’11, that the country couldn’t be divided more. And you go back to Obama’s campaign in 2008, you know, he was talking about the divide and healing the country and all of that. And some would argue on the right that he did more to divide the country than to unite it. I kind of reject that notion.” Why is that? “Because it wasn’t him!” Boehner replies. “It was modern-day media, and social media, that kept pushing people further right and further left. People started to figure out … they could choose where to get their news. And so what do people do? They choose places they agree with, reinforcing the divide.”

He continues: “I always liked Rush [Limbaugh]. When I went to Palm Beach I would always meet with Rush and we’d go play golf. But you know, who was that right-wing guy, [Mark] Levin? He went really crazy right and got a big audience, and he dragged [Sean] Hannity to the dark side. He dragged Rush to the dark side. And these guys—I used to talk to them all the time. And suddenly they’re beating the living shit out of me.” Boehner, seated in his favorite recliner, lights another cigarette. “I had a conversation with Hannity, probably about the beginning of 2015. I called him and said, ‘Listen, you’re nuts.’ We had this really blunt conversation. Things were better for a few months, and then it got back to being the same-old, same-old. Because I wasn’t going to be a right-wing idiot.”

Boehner believes Americans are ill-informed because of their retreat into media echo chambers, one of two incurable causes of the country’s polarization. Another is inextricably related: the unwillingness of lawmakers to collaborate across the aisle, for fear of recriminations from the base. Boehner says the fact he and Obama golfed together only once—and agreed that it was usually better for him to sneak into the White House—speaks to how the two parties punish compromise. He doesn’t foresee this toxic political climate improving, ticking off potential fixes—term limits, redistricting reform—that he says won’t make a bit of difference. “It’s going to take an intervening event for Americans to realize that first, we are Americans,” he says. An intervening event? “Something cataclysmic,” he responds, gazing upward.

Boehner often felt more welcome among Democrats than he did within his own party. When he made his retirement announcement, he told me, Obama called him and said, “Boehner, you can’t do this, man. I’m gonna miss you.” Biden feels the same way. “The only way we’re going to get this back together again,” he says, “is with some more John Boehners.”

The starkest divide in recent Washington has been between longtime pols like Boehner and Biden who yearn for a more amicable time, and newcomers who view the bitter acrimony of the Bush and Obama years as normal. The fever might have broken in 2016, Boehner says. But the parties chose the two most polarizing nominees in modern history. “The only Republican who Hillary Clinton possibly could have beaten was Donald Trump, and the only Democrat that Trump possibly could have beaten was Clinton,” Boehner smirks. “Three hundred and thirty million Americans, and we got those two.”

***

Boehner spent six hours getting photographed around the Capitol in September. He wore a salmon-colored tie for certain shots and a blue tie for others; the photographs will inspire his official portrait, which will probably be hung in the speaker’s lobby in late 2018—around the three-year anniversary of his departure. The ceremony will give Boehner occasion to see his old friends, as well as the “assholes.” It will also serve as an opportunity to consider his legacy.

As a young House member, Boehner was instrumental in cleaning up Congress. As a committee chairman, he wrote and ushered through one of the premier policies of the Bush administration—even if the results were not what he envisioned. And as speaker, Boehner accomplished more than conservatives will ever give him credit for: winning significant spending cuts under a Democratic president; protecting the overwhelming majority of Americans from a tax hike; keeping earmarks banned despite having every reason to bring them back; and his proudest accomplishment, finding a permanent “Doc Fix,” which solved a nagging problem with the Medicare payment formula and could produce nearly $3 trillion in savings over the next three decades.

“He came to Congress wanting to burn it to the ground,” says Sommers, his former chief of staff. “And by the time he left, he was the ultimate institutionalist.”

Yet that assessment will be overshadowed by posterity’s more existential observations: that Boehner’s 25 years in Washington saw the dissolution of a party, the vandalizing of a government and the splintering of a nation. That Boehner watched as the GOP transformed from the party of George H.W. Bush into the party of Donald Trump. That Boehner funded and helped recruit a class of majority-makers who ended up driving him from office and destabilizing the Congress he cares deeply about. The triumph of John Boehner is that he achieved reform and ascended to the speakership and often rose above the uncompromising dogma of both parties; the tragedy is that he came to Congress an insurgent only to be swallowed by the insurgency, and that he wasted key opportunities, as with the shutdown and immigration battles of 2013, to lead in a way that might have quelled it. “At times,” Sommers admits, “we fed the beast that ate us.”

Boehner’s own district is the ultimate case in point: His successor is Warren Davidson, who was endorsed by Jordan in the GOP primary and has since joined the Freedom Caucus. “He’s one of these guys that’s caught in two worlds,” Boehner says. “They helped him get elected, he felt allegiance to them, he signed up with them. But I’m not sure he’s really one of them.”

I didn’t see the famously weepy Boehner get emotional during our time together, with one exception. The night of the golf outing, Ed tells me that toward the very end of Boehner’s speakership he called his friend to share a poem called “Builder or Wrecker.” Debbie asks Ed to recite it. He obliges, and I glance over at Boehner. His face is contorted. By the end of the poem he is sobbing and unable to speak. “He’s a builder,” Ed whispers to me. “Not a wrecker.”

***

“Have you found your purpose?” I ask him outside the breakfast joint in Green Bay. Boehner shakes his head. “It will become clear. But you can’t force the big guy to give you an answer,” he says. “Just do the right things for the right reasons, and good things will happen.”

With that, we prepare to part ways. The two House speakers enjoyed an overtime thriller at Lambeau Field the day before. Now Ryan has flown back to Washington, where a circular firing squad awaits. As for Boehner, he’s jumping in a rental car and pushing farther north in Wisconsin, where Mick, his former staffer, owns a massive wooded property. There, the two will do what retirees do best—sit around and tell stories about the old days. It would make for a more restful experience if Boehner weren’t thinking, in the back of his mind, about his story being written—here and in the history books. It’s no wonder he can’t concentrate.

Boehner shakes my hand and smiles softly. “Be nice to me,” he says.

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