This study uses 2016 ANES data to explore the group of Americans who voted for Barack Obama in 2012 and Donald Trump in 2016, focusing specifically on the factors influencing this trajectory. The voting trajectory from Obama to Trump comprised approximately 13% of the actively voting 2016 electorate. I use bivariate analyses and multiple logistic regression models in order to provide an explanation for this voting trajectory, and to separately explore this group outside of the larger populous of Trump voters. The study finds that economic insecurity, misogyny, anti-immigrant sentiment, and racial resentment all had a significant effect on the likelihood of voting for both Obama and Trump for president, controlling for historically influential factors like political party identification and others. Anti-immigrant sentiment proved to have the largest effect on this voting group. The study concludes by calling for more research on this influential voting trajectory, as well as the other trajectories between 2012 and 2016, including non-voters.