Obama's health care challenge: keeping Democrats on board President Obama faces a dual challenge in the months ahead: Convince uninsured Americans to sign up for Obamacare and keep worried Democrats on board as the administration enacts his health care overhaul. The rollout of the Obamacare health exchanges Oct. 1 touched off a high-stakes messaging battle over the president's signature legislative achievement, a clash with enormous repercussions for the 2014 midterm elections. Playing an expectations game, Obama's surrogates have openly argued that it could take months, if not years, for Americans to fully appreciate the impact of a law that polls show has been greeted with confusion and skepticism. Obama's political allies don't have time to spare, however.