J. Scott Applewhite / AP

Who did John Boehner represent? Conservatives thought he was a sellout. Liberals thought he was a lightweight. His own deputies (first Eric Cantor, then Kevin McCarthy) disrespected him; his caucus was totally out of his control. He didn’t have any particular juice back home in Ohio. If he had a constituency at all, it was the ever-more-powerless Beltway Establishment, its own isolated and isolating club. For a man whose position—speaker of the House—bespoke power, he often seemed like the loneliest man in American politics.

So it was fitting that, when Boehner announced his retirement on Friday, it was a decision he had made in solitude. He had consulted no one; he had told only his wife and his chief of staff. McCarthy, the odds-on next speaker, got a two-minute heads up. The rest of Washington, and the country, was blindsided.

Before he became a congressman, Boehner was a blue-collar Ohioan. He started as a salesman and rose to president of a plastics company. (The second of 12 children, he must have spent his childhood overseeing a houseful of less mature beings, a situation with obvious parallels to his eventual position.) He was frank and profane, liable to break into tears out of joy or despair, and incapable of maintaining a poker face. He ate breakfast every morning at the same Capitol Hill diner. When he went home to Cincinnati, he cut his own grass. He liked his cigarettes, a nice Merlot, golf, good suits (and making fun of other people’s). He believed in the Chamber of Commerce’s agenda: More immigration, less Social Security—the opposite of Trumpism, and a philosophy with very little popular support outside of K Street. Boehner was a sort of Everyman of American Capitalism; his resignation can be seen, in part, as the ultimate frustration of the GOP's status-quo-oriented business wing, which has funded the party to ever greater legislative success only to see its priorities ignored in favor of attention-getting brinkmanship.

There are two rules of John Boehner, John Lawrence, a former chief of staff to Nancy Pelosi, told me recently: One, he always wants to make the deal; two, he can never deliver the votes for the deal. That was apparent even before he became speaker. In 2008, with the nation’s economy melting down, Boehner, then the House minority leader, worked with Democrats to craft a bailout bill for the financial industry. But when it went to the floor, he couldn’t get Republicans to vote for it. The bill failed, and the stock market plunged nearly 800 points. (A second version of the bill passed a few days later.)

After the Tea Party wave of 2010 elevated Boehner to the speakership, the White House saw him as someone it could deal with, and Boehner and President Obama set about trying to craft a “grand bargain” that would increase government revenue while cutting long-term spending. The deal fell apart—the two sides still disagree on what happened, with Democrats insisting Boehner couldn’t sell a deal to his caucus while Republicans say it was the White House that made unreasonable demands at the last minute. The result, in July 2011, was a debt-ceiling crisis that brought the country to the brink of default and resulted in a credit downgrade.

This pattern—failed dealmaking, crisis, a last-minute (or post-last-minute) patch—would repeat itself. Boehner was backed by a large Republican majority, and was himself quite ideologically conservative. But he believed in compromise, in incremental progress toward conservative goals in the long term. And as a congressional lifer, he’d been around long enough to know what was realistic—given a Democratic Senate and White House—and what was not. Several dozen members of his GOP caucus, elected from overwhelmingly Republican districts, often in race-to-the-right primaries, disagreed with this analysis and viewed compromise as capitulation. (This is also the view of the majority of the party base.)

Thanks to this conservative rump caucus, Boehner couldn’t reliably get the 218 votes he needed to pass legislation through the House. He suffered a series of humiliating failed floor votes; he repeatedly had to rely on Democratic votes to get bills through. The situation came to a head two years ago, when conservatives, led by Senator Ted Cruz, refused to vote for a funding bill to keep the government up and running unless a measure to defund Obamacare was included. With Boehner unable, again, to muster the votes for a compromise, the government shut down for two and a half weeks.

It reopened again just in time to raise the debt ceiling. Boehner was convinced he had taught the conservatives—one moderate GOP congressman termed them “lemmings with suicide vests”—a lesson. And indeed, 2014 saw a marked thaw, with a budget passing both houses for the first time in five years and some minor outbreaks of comity. At the same time, Boehner couldn’t convince his troops to move forward on immigration, an issue dear to the speaker’s base in the business lobby.

Why was Boehner so weak? In part, he was simply a man with an impossible job. Republicans are divided between their nihilist and governing wings. Having banned earmarks, Boehner couldn’t use pork-barrel spending to win votes. And with his naturally easygoing temperament, he wasn’t an enforcer—unlike the former Majority Leader Tom DeLay, no one would ever nickname John Boehner “the Hammer.” Boehner’s efforts to punish those who defied him—by stripping committee assignments, for example—were only met with more defiance. In the vote to reelect him speaker in January, 25 Republicans voted against him, the greatest number of defections any speaker has faced in the last century.

Boehner was said to like being speaker, but most days, he didn’t seem to be having much fun. For years, there have been rumors he would resign. At his press conference Friday, he said he initially planned to depart at the end of 2014, but when Cantor was deposed in a primary last year, he decided to stay one more year, for stability’s sake. Last year’s midterm elections increased the Republicans’ majority and seemed to increase Boehner’s power. But they also increased the ranks of restive conservatives, who helped torpedo another business-lobby priority, the Export-Import Bank, over the summer.

Next week, funding for the government will again expire, and Boehner was looking ahead at another apparently unavoidable shutdown fight, as conservatives demanded that Planned Parenthood be defunded in exchange for any extension. In the end, he realized he had one last bargaining chip—his speakership. Without the threat of an ouster looming over him, he is free to put a “clean” funding bill on the floor, which is likely to pass with a combination of Democratic and Republican votes.

Boehner’s exit Friday was cheered by conservatives, from the halls of the Values Voter Summit to the airwaves of talk radio. After years of struggling against his own party’s rejectors of compromise, he has finally pleased them by giving up. He sacrificed his career for one last deal. This time, he may even have the votes to pass it.

We want to hear what you think about this article. Submit a letter to the editor or write to letters@theatlantic.com.