This chapter examines what happened to political advertising in 2016, how effective was it, how did it compare to past years, and what might the future hold. The big story of the 2016 Republican primary season was the unexpected rise of Donald Trump without the traditional trappings of a vast organization, large media buys, and a typical campaign structure. According to an article in Politico, Trump foreshadowed his presidential campaign strategy in December 2013 before a gathering of New York political professionals. Unlike the Republican primary race, money and paid television did make a difference for the Democrats. Large expenditures were earmarked for television advertising, particularly by the Clinton campaign. Clinton aired 187 unique spots over the course of the entire election season while Trump ran just 40 unique television spots. In the general election, 80 percent of the presidential ads were either negative or contrast ads.