John Boehner's Tough Choice

Boehner must decide between most extreme members of his caucus and a compromise.

Speaker of the House John Boehner, R-Ohio, answers questions at a press conference at the Capitol on Sept. 26, 2013 in Washington, D.C.
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When he rose to the role of speaker on Jan. 5, 2011, Rep. John Boehner, R-Ohio, assumed the gavel as he wiped tears from his eyes. He pledged to reign in the role of the federal government and reverse the course of President Barack Obama's legislative agenda. He looked out onto a fresh-faced caucus, 87 new Republicans had made the moment possible.

"No longer can we fall short. No longer can we kick the can down the road. The people voted to end business as usual, and today, we begin to carry out their instructions," Boehner said.

There was no sign that doing any business at all would become quite so problematic.

[READ: Republican Leaders and Americans Look to Reforms on the Debt Ceiling]

During his tenure as the speaker, Boehner has never known a time when his caucus has been subdued, willing to let this or that fight slide, or go with the flow in the name of prodding essential policies along. From debt ceiling to food stamps, a coalition of Republicans in the House has clearly established its own agenda, a rallying cry to only do what their conservative constituents back home urge them to no matter the costs. "These folks are not really interested in being part of the team and moving in a direction that benefits the team," says former Rep. Steve LaTourette, R-Ohio, a close ally to Boehner who retired in 2013. "He is like the emperor with no clothes."

Boehner has a big decision to make this weekend. While the country stares at a government shut down looming, Boehner will finally have to decide if the will of his most conservative caucus is the will of the House, or whether it is time to leave those members behind.

There are only four days left for Boehner to get his caucus united behind a funding bill, send it back to the Senate and get it signed by the president before the government shuts down.

At this point, Boehner has become accustomed to lurching from one fiscal fight to the next, the latest crisis is the third major showdown the speaker has presided over.

Through it all, Boehner's spokesman Michael Steel says the speaker's leadership style has remained the same.

"He is open and honest and up front with everyone he meets," Steel says. "He works hard with the team to establish goals from the team and for the team...he has certainly learned things along the way."

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In the summer of 2011, Boehner met for months with Obama in closed-door meetings. But the "merlot and Nicorette" sessions intended to broker a deficit-reducing package in exchange for a debt ceiling hike, came to a halt. Republicans thought they had a deal with the White House – $800 billion in new tax revenue in exchange for more than $3 trillion in spending cuts. But when the bipartisan "gang of six," a few days later, released more than $1 trillion in new revenue, the dynamic changed (how is a point of contention). Republicans and Democrats both pressed their leaders to push for more, the country's credit rating was downgraded and the Budget Control Act was born.

[READ: Republicans Risk Shutdown on Obamacare]

Since then, Boehner has been a reluctant negotiator with the White House, telling reporters that he won't be gallivanting back and forth to the White House to resurrect a bipartisan debt ceiling negotiation ahead of the Oct. 17 deadline. "I'm not doing that," he told Politico on Sept. 19.

"After August 2011, there was a breakdown in trust between the White House and the House," says LaTourette. "After that deal blew up, [Boehner] said 'there's no point in talking to that guy anymore.'"

For future negotiations, Boehner turned inward to his caucus for support and leverage. At the end of 2012, with automatic budget cuts and a tax hike on the horizon, Boehner looked to unite his members in a GOP plan he could present to the White House and Senate Majority Leader Harry Reid as a bargaining chip. But members were reluctant to unite behind Boehner's "plan B," which would have permanently extended Bush-era tax cuts for individuals making less than $1 million a year.

Republicans didn't want taxes to increase on anyone.