Speaker John A. Boehner’s legacy falls short of what he hoped when he took the gavel from Nancy Pelosi, at a time when talk of grand bargains abounded and a host of long-festering issues seemed ripe for action.

The Ohio Republican’s biggest legislative accomplishment came with President Barack Obama’s signing the 2011 budget agreement spurred by Boehner’s demand for trillions in spending cuts in return for a debt limit increase. That set the stage for a decade of fiscal restraint and the first real cuts in government spending in years despite having a liberal president in the Oval Office.

While Obama frequently touts the deficit reduction on his watch, it was Boehner who put his spending aspirations in a vise.

“We’re now on track to cut government spending by $2.1 trillion over the next 10 years, we’ve made the first real entitlement reform in nearly two decades, and we’ve protected more than 99 percent of the American people from an increase in their taxes,” Boehner said as he began his resignation news conference Friday.

But Boehner had wanted so much more.

Obama Calls Boehner ‘A Good Man’

That 2011 agreement only came after months of secret negotiations with the president on a sweeping grand bargain on entitlements and revenue fell apart, and in the years that followed, Boehner had to face the near-constant threat of revolt in his own ranks.

He was repeatedly undermined by some of his lieutenants and a suspicious right wing, egged on by a constellation of conservative groups, websites and talk-show hosts who thrived on condemning the compromises necessary to keep the government operating with a Democrat in the White House and Harry Reid wielding power in the Senate.

After Obama’s re-election and the fiscal cliff crisis came and went, Boehner was railroaded by his own conference in 2013 into a government shutdown to defund Obamacare.

The demands of the right, in Boehner’s view, were incompatible with the reality of power in Washington. Controlling part of one of the three branches of government, as he would point out, wasn’t enough to defund Obamacare or undo Obama’s regulations.

And having lived through the government shutdown fight in 1995, Boehner didn’t think a shutdown would help Republicans or succeed in extracting concessions from a re-elected president.

Republicans eventually caved.

Boehner also hoped to get his flock to embrace an immigration overhaul, seeing it as an imperative for his party after Mitt Romney’s abysmal showing with the fast-growing Hispanic population. That ran into a buzz-saw of opposition, with fewer than 20 Republicans willing to publicly sign on to his principles a few months later.

After Majority Leader Eric Cantor’s stunning primary loss, and facing the certainty of a revolt, he shelved his immigration ambitions and blamed Obama.

Smaller wins, such as a “doc fix” bill earlier this year, which Boehner touted would save trillions in Medicare over future decades — though add to it in the first 10 years — did little to burnish his reputation with the right. (Nor did the kiss Boehner planted on Pelosi, D-Calif., his partner in passing that bill, in the Rose Garden to celebrate.)

Other grand efforts, such as oft-promised attempts to “replace” Obamacare and overhaul the tax code, never made it to the House floor on his watch.

The warning signs for Boehner were there early on — almost from the start he has needed to rely on Democratic votes to pass any bill that would both keep the government open and get Obama’s signature.

A series of slights outraged the right, including a voice vote to extend a payroll tax cut when most lawmakers had gone home for the holidays, and a snap voice vote for an earlier doc fix that caught many away from the chamber.

Over time, Boehner’s go-to moves — show votes on Republican priorities and lawsuits where the GOP felt Obama was going beyond the bounds of the law — wore thin.

Without the earmarks he had himself eliminated, his ability to punish his own members was limited, and when he or his lieutenants did try to punish apostates by taking away committee assignments, it tended to backfire by creating a core of malcontents who relished in plotting his demise.

The president has repeatedly talked fondly of Boehner personally but has seen him as too weak to be a real partner for dealmaking.

Obama, who for years had hoped for a bipartisan grand bargain breakthrough, finally seemed to realize that one wasn’t going to happen.

After winning re-election, Obama warned Boehner he would no longer give him anything in return for another debt limit increase. Facing a potentially catastrophic default, Boehner blinked, and his “Boehner Rule” — requiring a dollar in deficit cuts for every dollar of debt limit hikes — effectively headed for the dustbin.

In the past year in particular, Obama has been the one threatening the GOP on budget issues, demanding a partial reversal of the 2011 spending cuts. And he’s ramped up his executive actions on a host of issues from carbon emissions to overtime rules, with the new Republican Congress unable to stop him.

But Obama still needs Congress to keep the lights on. Boehner’s decision to advance a short-term “clean” continuing resolution means that’ll be easier for now, but a longer-term budget deal will be needed this fall, not to mention another debt limit hike, a highway bill deal and plenty more before Obama heads for the exits, all with the 2016 presidential election ramping up in the background.

Obama, for his part, said Friday he wishes Boehner well and hopes the next speaker learns lessons about the necessity of compromise.

“I don’t necessarily think that there’s going to be a big shift,” he said. “I do think that Speaker Boehner sometimes had a tough position because there were members in his caucus who saw compromise of any sort as weakness or betrayal and when you have divided government, when you have a democracy, compromise is necessary. And I think Speaker Boehner sometimes had difficulty persuading members of his caucus that. Hopefully they’ve learned some lessons from 2011. … I expect we’ll continue to have significant fights around issues like Planned Parenthood and significant fights around issues like immigration. But perhaps the visit by the Holy Father to Congress may have changed hearts and minds.”

Obama spoke optimistically about this week’s papal visit, which seemed pivotal for the Catholic Boehner.

“At a moment when, in our politics, so often the only way you get on the news is if you’re really rude or you say really obnoxious things about people, or you insist that other people points of view are demonic or evil and leave no room at all for the possibilities of compromise, you know, I’d like to think that spirit will continue to permeate Washington for some time to come. And I know that, in his heart, that’s who John Boehner was,” Obama said. “It was sometimes hard to execute.”

Related:

Obama Praises Boehner, Hopes Republicans Learn Lesson (Video)

Pope Challenges Congress to Act on Climate, Immigration, Economy (Updated)

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