This article compares Michelle and Barack Obama’s coronal stop deletion (CSD) rates in different contexts at different time points in order to examine the effects of time and context on an aspect of the speech of these black political figures. Data are taken from each of the Obamas’ speeches from the 2012 and 2016 Democratic National Conventions as well as two joint interviews from 2012 and 2016. Results of regression models indicate that Barack and Michelle Obama’s CSD is systematically subject to contextual, phonological, and morphological constraints. Results indicate differences between phonological and morphological conditioning effects observed for each speaker, evidence that Barack and Michelle employ this variable differently, perhaps due to different dialect backgrounds and social expectations, with Michelle patterning more like African American English speakers in earlier studies than Barack. Results show how CSD may be a useful variable for understanding patterns of style in the linguistic behavior of individuals.