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CaribbeanDee-Ann Kentish-Rogers is a 2021 Millennium fellow, lawyer, former government minister, and advocate whose work sits at the intersection of governance, legislative reform, and cross-border leadership. From 2020 to 2025, she served in the government of Anguilla, a British Overseas Territory in the Eastern Caribbean known for its domain name, “.ai.” She was elected and became the youngest minister in the territory’s history, holding the portfolios for education, social development, creative industries, and sports.
Taking office amid an acute fiscal crisis, she contributed as a cabinet member to the fiscal, debt-management, and public-finance reform decisions that cut Anguilla’s public debt by 38.7 percent between 2020 and 2025, from 476.9 million to 292.4 million Eastern Caribbean dollars. She also championed child-justice legislation and programs designed to turn young people’s potential into real economic participation. She served as the government-appointed member of the CARICOM Economic Development Committee and on the Finance and General Purposes Committee of the University of the West Indies.
She read law at the University of Birmingham and was called to the Bar of England & Wales at Middle Temple Inns of Court in 2018. She now practices civil and banking law in Anguilla; serves as a leadership ambassador with Global Namibia One, a tourism and trade platform; and is an ambassador for A-Sisterhood, mobilizing partnerships for survivors of acid attacks, female genital mutilation, and domestic violence. In 2018, she was also crowned Miss Universe Great Britain, the first Black woman to hold the title.