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

Speaker John BoehnerJohn Andrew BoehnerFormer top Treasury official to head private equity group GOP strategist Steve Schmidt denounces party, will vote for Democrats Zeal, this time from the center 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 BoehnerJohn Andrew BoehnerFormer top Treasury official to head private equity group GOP strategist Steve Schmidt denounces party, will vote for Democrats Zeal, this time from the center 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 BrownThe Hill's Morning Report — Sponsored by PhRMA — GOP lawmakers race to find an immigration fix Warren to put hold on Trump consumer bureau nominee Stop labeling babies as 'born addicted' — it stigmatizes them and is inaccurate 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 Mason ReidAmendments fuel resentments within Senate GOP Donald Trump is delivering on his promises and voters are noticing Danny Tarkanian wins Nevada GOP congressional primary 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.