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

Speaker John BoehnerJohn BoehnerGOP rushes to vote without knowing full impact of healthcare plan Dem senator to reintroduce ‘buy American’ legislation GOP senators offer bill to require spending cuts with debt-limit hikes 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 BoehnerGOP rushes to vote without knowing full impact of healthcare plan Dem senator to reintroduce ‘buy American’ legislation GOP senators offer bill to require spending cuts with debt-limit hikes 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 BrownThe Hill’s Whip List: Where Dems stand on Trump’s Supreme Court nominee Senators war over Wall Street during hearing for Trump's SEC pick Sanders to oppose Gorsuch's nomination 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 ReidThis obscure Senate rule could let VP Mike Pence fully repeal ObamaCare once and for all Sharron Angle to challenge GOP rep in Nevada Fox's Watters asks Trump whom he would fire: Baldwin, Schumer or Zucker 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.