It has been widely assumed the Tea Party paved the way for Donald Trump’s electoral victory in 2016. Yet, little research has examined the transition from the Tea Party’s takeover of the Republican Party to Trump’s subsequent capture of the GOP. This chapter examines the Tea Party’s engagements with Donald Trump between 2009 and 2018. Tea Party activists initially admired Trump’s amplification of the birther conspiracy theory, which falsely claimed that Barack Obama was not a natural born citizen. However, activists dismissed or ridiculed Trump’s political ambitions. By 2013, activists had warmed to Trump’s positions on Islam and immigration, but still did not view him as a viable political candidate. After Trump won the 2016 election, there was a sea shift in tone, as the remaining Tea Party activists enthusiastically embraced his America First agenda. These observations are corroborated by an analysis of the impact that Tea Party activism had on the 2016 Republican primaries for president and the general election. Our analyses shows that Tea Party activism had little impact on helping Trump become President, consistent with the insurgency’s larger ambivalence about Trump’s candidacy.