Player of the Week: Speaker John Boehner (R-Ohio)

Speaker John BoehnerJohn Andrew Boehner‘Lone wolf’ characterization of mass murderers is the epitome of white privilege Pelosi urges Ryan to create select committee on gun violence Ex-congressman Michael Grimm formally announces bid for old seat MORE (R-Ohio) has the toughest job in Washington.

He is trying to strike a debt deal with President Obama, who has much better negotiating leverage following his reelection victory last month.

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Obama insisted that tax revenue be included, so John BoehnerJohn Andrew Boehner‘Lone wolf’ characterization of mass murderers is the epitome of white privilege Pelosi urges Ryan to create select committee on gun violence Ex-congressman Michael Grimm formally announces bid for old seat MORE put $800 billon of it on the table. But the president wants more, pushing for $1.6 trillion and demanding that tax rates go up as part of any pact.

Boehner has previously crowed about agreements he has struck with Obama, saying, for example, that he got “98 percent” of what he wanted in last summer’s debt-ceiling deal. It is a good bet he won’t be bragging quite so loudly this time around if a deal is reached.

Any deal must pass both houses of Congress, and Boehner needs to show his GOP conference that he has not come away empty-handed from his talks with Obama.

Recently, Sen. Sherrod BrownSherrod Campbell BrownDems plan to make gun control an issue in Nevada Mandel leads GOP primary for Ohio Senate seat: internal poll Red-state Dems need more from Trump before tax embrace MORE (D-Ohio) suggested that an agreement could pass the House with 180 Democrats and 50 Republicans voting yes. That is highly unlikely. Such a voting ratio would imperil Boehner’s Speakership.

Obama knows that he must give Boehner tangible items in return for raising taxes on the top 2 percent of income earners. But what will they be? Senate Majority Leader Harry ReidHarry ReidChris Murphy’s profile rises with gun tragedies Republicans are headed for a disappointing end to their year in power Obama's HHS secretary could testify in Menendez trial MORE (D-Nev.) says Social Security shouldn’t be touched. Other Democrats insist that benefit cuts to Medicare and Medicaid are non-starters.

But raising the eligibility age and means-testing Medicare are nevertheless both being considered. Adjusting the cost-of-living formula for Social Security could also be in the mix.

Boehner is already taking fire from conservative-leaning groups, and it is likely he will have to concede more to Obama than he has already offered. In his 22 years in the House, Boehner has crafted many legislative deals. This one will be the most challenging of his career.