With Obama's re-election giving Democrats more leverage over Republicans, and far-right critics pushing a #FireBoehner hashtag on Twitter, Boehner is in an incredibly tight spot.
To which the undaunted speaker responds, "I remain the most optimistic person in this town."
Dealmaker • The baritone-voiced Boehner has a reputation as a deal-maker and a survivor. At least within his own party, he may be in a better place now than he was during a rough first two years as speaker that produced few solid accomplishments, pushed big budget decisions down the road and saw already-low congressional approval ratings sink even further.
The election that felled presidential nominee Mitt Romney, thrashed Senate Republicans and narrowed the GOP majority in the House also rid some of the loudest tea party voices in Boehner's fractious caucus and gave pause to other Republican legislators who felt their speaker had been too accommodating of Democrats in 2011 debt negotiations. Those talks collapsed at the 11th hour.
Now Obama and Boehner are right back at it, negotiating in person, by phone and by intermediaries, as they trade offers and counteroffers over huge questions about tax rates and spending. Obama wants more tax revenue, Boehner more spending cuts.
Questions about how far Boehner can be pushed, and at what personal price, are swirling everywhere.
Legacy • Boehner may well be known for his tan, and for tearing up easily, but he's no pushover, says Alan Simpson, a Republican who was co-chairman of the president's deficit commission.
"He's strong and he's used to taking a lot of crap," says Simpson. "Once you're in that situation, you're going to work your way through."
Ron Peters, a University of Oklahoma professor who's written extensively about House speakers, said the fate of the talks may come down to Boehner asking himself, "as all speakers do: What do I want to be remembered for?"
"He's in a position to do something historic," says Peters. "And so what he needs to do is lead the Republicans through the process to get the deal that will become a legacy."
It's a huge moment for a speaker who grew up as one of 12 children in a working-class family in suburban Cincinnati, helping out in his father's bar. That upbringing taught Boehner important skills for managing his raucous Republican fold, including an often under-rated ability simply to let people vent.
Obama drew a colorful sketch of his negotiating partner during the 2011 budget talks, as quoted by author Bob Woodward: "He's a golf-playing, cigarette-smoking, country-club Republican who's there to make deals."
Boehner helped fill out that portrait as he described the scene at one of their negotiating sessions.
"All you need to know about the differences between the president and myself is that I'm sitting there smoking a cigarette, drinking merlot, and I look across the table and here is the president of the United States drinking iced tea and chomping on Nicorette," he told Woodward.
Beyond golf, the two "really don't have a whole lot in common," says Rep. Steve LaTourette of Ohio, a friend of the speaker.
"Boehner loves to tell stories about growing up in a bar," says LaTourette. "He really is a self-made guy, and the president is a professor. And that's a little bit like oil and water in terms of being best buds. But they don't have to be best buds."
LaTourette says Boehner has been managing the pressure with his trademark even temperament. "If he's all tied up in knots and tense, it has to be way deep inside him because you don't see it on the surface. It's true, he doesn't even cry as much anymore."
Boehner has taken a ribbing for years about his penchant for choking up over big moments, little kids and just about anything in between.
In return, the smartly dressed speaker likes to tease colleagues and reporters alike about their sartorial shortcomings.
"Tie's a little long today, isn't it?" he deadpanned to one reporter as he walked through the Capitol on Wednesday.
Not a fun job • Boehner, who lives in a basement apartment in Washington while his wife stays in Ohio, is putting in longer hours these days but still keeps largely to his usual routine. He's up early to check news sites and perhaps get in a walk before breakfast at a diner, then on to Capitol Hill by 9 a.m. He's typically in bed by 10 p.m.
"The quality of life is not like it was before he was speaker," says Rep. Pat Tiberi of Ohio, a longtime friend of the speaker. "He doesn't play golf as much. He travels and helps members. I wouldn't say it's a very fun job."
Boehner still shows flashes of his dry humor, though.
He drew laughs for dishing off a rhyming dodge to reporters Thursday when asked if he would allow separate votes on middle-income tax rates and rates for the wealthy.
"Ifs, ands and buts are like candy and nuts," he said. "If that's the case, every day would be Christmas."
Presiding over the lighting of the Capitol Christmas tree, Boehner took time to fuss over the optics of his photo op with a Colorado high school student invited to turn on the lights.
"Now here, button your coat, button your coat, c'mon," he gently admonished Ryan Shuster, of Colorado Springs. "Ryan, pictures last forever, OK?"
The speaker, who ran a plastics and packaging business before his life in politics, is known for his down-to-earth descriptions of the dynamics on Capitol Hill.
Speaking about the difficulties of leading his diverse caucus, he once explained: "It's hard to keep 218 frogs in a wheelbarrow long enough to get a bill passed," referring to the number of votes needed to approve legislation.
Boehner's frequent travel and work on behalf of fellow House Republicans in the run-up to the 2012 elections are one reason that losses in the House were minimized and loyalty to the speaker maximized. He raised more than $97 million for Republicans running for Congress, traveling almost nonstop for the last 45 days leading up to elections.
But the conservative griping and uncertainty about the debt talks have raised speculation that Boehner could face a challenge in January's leadership elections.
Boehner insists he's not worried about his position, but rather about "doing the right thing for my kids and grandkids."
Boehner's supporters think that if it comes down to a choice between his job and a deal that puts the country on a better economic path, the speaker would choose the latter.
"I don't think he's here to do small things," says John Feehery, a former top House Republican aide.