Wasserman is a well-known expert on U.S. elections and political geography. In Fall 2016, he drew praise for his accurate pre-election analysis, including his piece, "How Trump Could Win the White House While Losing the Popular Vote," written two months before election day. Wasserman served as an analyst for the NBC News Election Night Decision Desk in 2016, 2012, and 2008 and has appeared on NBC Nightly News, ABC World News, C-SPAN Washington Journal, CNN, and NPR. He is a frequent contributor to FiveThirtyEight.com and his commentary has been cited in numerous outlets including POLITICO, the New York Times, the Washington Post, the Wall Street Journal, the Economist, and RealClearPolitics.