Previous research has characterized those resisting slavery as quite atypical of the enslaved population: most of them being young, male, and engaged in particular occupations. In this article, we study transgressive behavior among an enslaved population quantitatively. We employ a unique census from the Caribbean island of St. Croix in 1846, which allows us to study not only the characteristics of those that transgressed the masters' order in some way, but also to compare them with those of the entire enslaved population on the island. We find that the individuals in our dataset who transgressed the oppressive institution were, in many respects, quite typical of the entire enslaved population under study. Opposition to the oppressive system could be found among all groups of enslaved persons in the studied society. Nonetheless, we find that specific characteristics, such as marital status and gender, were more likely to be associated with transgression on St. Croix.