Jamil Smith, senior national correspondent for MTV News, Tricia Rose, director of the Center for the Study of Race and Ethnicity in America at Brown University, and Jonathan Alter, former editor of Newsweek, analyst for MSNBC, Daily Beast columnist and the author of The Center Holds: Obama and His Enemies, participate in a discussion drawing on the Obama administration's significant milestones and how future generations might experience his legacy.

It's come down to Obamacare vs. Being the First Black President. Tell us — how will President Obama be remembered? Vote in the final Baracket matchup!