For President Barack Obama and his administration, the last few weeks of 2014 were dramatically different from the rest of the year.

Up to that point, 2014 had been characterized by a series of crises, culminating in the crushing blow of the November midterms. And yet, in less than two months, the White House managed to secure a historic climate treaty with China, a revamped relationship with Cuba and long-sought action on immigration. As Obama boarded the plane in mid-December for his Hawaiian vacation, public polling suggested that a year of distinctly crappy numbers might be fertilizing a home-stretch bloom.

Many of the president's supporters are now wondering: Could all of it have come sooner?

In a "Drinking & Talking" exclusive, senior adviser Dan Pfeiffer makes the case that no, it couldn’t. Had the president moved before the election, Pfeiffer argues, his agenda would have been overwhelmed by politics, rather than shaping them.


Pfeiffer spoke with The Huffington Post's Jen Bendery and Sam Stein about what he thought was the most difficult achievement of the year (Cuba) and the bitter pills the White House has had to swallow.

He acknowledged that the administration is “not comfortable” with the legacy it's leaving on campaign finance, having had to sign off on a year-end spending bill with a provision allowing much larger donations to political parties. He also pledged to work with Democrats to try and fix a provision in that spending bill that allows banks to operate in the risky derivatives market with a federal insurance backstop.

“There is a trade-off here,” said Pfeiffer, when asked about Sen. Elizabeth Warren’s (D-Mass.) call to arms to rip out that provision. “Sometimes substantive gain comes at the cost of message purity.”

Over the course of an hour, Pfeiffer discussed some of the lighter moments of the past 12 months (such as Obama’s much-maligned sartorial choices) and some of the tougher debates (like not prosecuting torture). He also laid down some markers for the year ahead. The president, said Pfeiffer, would veto a bill to fund the Department of Homeland Security if it included a rider that nullified his executive action on deferred deportation.

Pfeiffer touched on campaigns past, noting that at one time Obama worried about former Republican presidential candidate Mitt Romney getting credit for the economic recovery. He also addressed campaigns to come, comparing former Florida Governor Jeb Bush (R) to a character from HBO's "The Wire" (specifically, Dennis "Cutty" Wise, an over-the-hill drug enforcer who ends up running a neighborhood gym).

Finally, Pfeiffer addressed the possibility of Obama, in his era of lame-duck liberation, going completely #YOLO on weed policy.

“Where is this on the HuffPo bucket list?” he asked.


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