Rahm Emanuel
White House chief of staff
Emanuel was chosen as chief of staff over other contenders in part for this very kind of moment. Famous for using sticks to get his way, he is underrated in his well-timed deployment of carrots as well. His years with the Clinton White House, as a member of Congress from Chicago and in the House leadership give him a hyper-realistic sense of what the political traffic will bear. He has orchestrated the Administration's largely hands-off-approach in public as the House and Senate work their legislative wills, but behind the scenes he has monitored every jot and swerve, offering helpful advice and the occasional characteristic threat. At some point this year, he'll tell the President that "now's the time," and together they will make one big push to get this done.