The living document that is a constitution gave life to the democracies of the countries of the English-speaking Caribbean. In the 1960s–1970s, when most of the Caribbean became independent from Britain, many constitutional issues arose. Should there be a written constitution? If so, should it simply reflect the Whitehall model? Should it be adapted to Caribbean realities? How can it be adapted to Caribbean realities? These were some of the questions that influenced the constitutional choices states made at the time of independence. Today, in 2024, these are still the relevant questions that must be asked, confronted, and explored. These questions are explored in the following interview with Prof. Hamid Ghany, one of the foremost political analysts and Constitutional Law scholars in the region and Justice Althea Alexis-Windsor, a judge of the Supreme Court of Trinidad and Tobago who also serves as a judge of the International Criminal Court in the Netherlands. It is more than an interview. It is a meeting of the minds—between academia and practitioner—that reveals a belief in the power and purpose of Caribbean constitutions. The interview explores the underpinning of Caribbean constitutions, their role as public policy tools, the persistent challenges they face, and the possibilities for how our living constitutions can both shape our societies and be shaped by our societies.