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

Speaker John BoehnerJohn BoehnerIt's time for McConnell to fight with Trump instead of against him How Republicans can bring order out of the GOP's chaos Republican donor sues GOP for fraud over ObamaCare repeal failure 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 BoehnerIt's time for McConnell to fight with Trump instead of against him How Republicans can bring order out of the GOP's chaos Republican donor sues GOP for fraud over ObamaCare repeal failure 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 BrownOvernight Finance: House passes spending bill with border wall funds | Ryan drops border tax idea | Russia sanctions bill goes to Trump's desk | Dems grill bank regulator picks Dems grill Trump bank regulator nominees Senate Dems launch talkathon ahead of ObamaCare repeal vote 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 ReidOPINION | 5 ways Democrats can win back power in the states THE MEMO: Trump's base cheers attacks on McConnell It's time for McConnell to fight with Trump instead of against him 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.