Globally, on any given day, an estimated three million persons are behind bars on pretrial detention awaiting trial in conditions that are similar to or worse than those of convicted individuals. Pretrial detention is warranted on legal grounds; however, it is argued that excessive pretrial detention has the propensity to act as a form of human rights abuse, whittle away the Rule of Law and emasculate the presumption of innocence. In Trinidad and Tobago, pretrial detention is quite noticeable as approximately two-thirds of all incarcerated adults on the island at the end of 2018 were pretrial detainees. This chapter uses data gathered by the Trinidad and Tobago Prison Service to determine whether the usage of pretrial detention in Trinidad and Tobago is akin to a human rights abuse, whittles away the Rule of Law and/or emasculates the presumption of innocence. This chapter focuses on the important, yet underappreciated issue of pretrial detention in an island context. Further, this chapter presents a nascent effort to catalogue the deleterious impacts of the excessive use of pretrial detention in Trinidad and Tobago, contributes to the literature by addressing an existing gap in pretrial detention scholarship in the Caribbean, and can assist Trinidad and Tobago’s government to better understand and design policy responses to pretrial detention.