Dee-Ann Kentish-Rogers

Dee-Ann Kentish-Rogers (born 13 January 1993) is an Anguillan politician, lawyer, athlete, former model and beauty pageant titleholder. A member of the Anguilla Progressive Movement, Kentish-Rogers served as the Minister for Education and Social Development in the government of Ellis Webster from 2020 until 2025. She also represented the constituency of Valley South in the House of Assembly from 2020 until 2025. Kentish-Rogers lost reelection in the 2025 Anguillian general election, when the Anguilla United Front took control of the government. Since 2021, she has been a Millennium Fellow at the Atlantic Council in Washington, D.C.

Kentish-Rogers first received national recognition in athletics, competing for Anguilla at the 2010 and 2014 Commonwealth Games, and at the 2012 CARIFTA Games. She afterwards became a model and beauty pageant titleholder, winning Miss Anguilla 2017 and Miss Universe Great Britain 2018, where she was the second Black British woman after Anita St. Rose in 1996 to win the title. Kentish-Rogers later went on to place in the Top 20 at Miss Universe 2018 as the British representative.

Early life, athletics, and education Kentish-Rogers was born on 13 January 1993 in The Valley on the island of Anguilla, a British Overseas Territory in the Caribbean, and was raised on her family farm. Growing up, Kentish-Rogers resided in a house with 11 other family members, including several male cousins, and was a self-described "tomboy" who played football. While competing at the 2014 Commonwealth Games, she suffered a knee injury which put an end to her athletics career. The pageant was held on 14 July 2018 in Newport, Wales, and Kentish-Rogers went on to be declared the winner. She was the first Black British woman to win the title.

As Miss Universe Great Britain, Kentish-Rogers received the right to represent Great Britain at Miss Universe 2018. The pageant was held on 17 December 2018 in Bangkok, where she reached the top 20.

Political career Kentish-Rogers began a political career in 2020, after announcing her candidacy on behalf of the Anguilla Progressive Movement (APM) in the 2020 general election. Kentish-Rogers was selected to contest the Valley South constituency for the Anguilla House of Assembly, standing against incumbent premier Victor Banks. The election was held on 29 June 2020, where Kentish-Rogers was elected to the Anguillan parliament. Party leader Ellis Webster later took office as premier and formed a seven-person government, nominating Kentish-Rogers to serve as education and social development minister. In February 2022, Kentish-Rogers served as acting premier for ten days, while Webster was not present in Anguilla; aged 29, she became the youngest person to serve in the position in Anguillan history. In June 2023, Kentish-Rogers resigned from the government and from the APM in protest of the government's handling of the implementation of the goods and service tax (GST), but was reappointed one week later.

Kentish-Rogers stood for reelection in the 2025 general election, but was defeated in her constituency by Cordell Richardson of the Anguilla United Front (AUF). The AUF flipped four seats in the House of Assembly which were held by the APM, and took control of the government, led by Cora Richardson-Hodge. Kentish-Rogers's also resigned as education and social development minister, and was succeeded by Shellya Kenisha Rogers-Webster of the AUF, under the title of social development minister.

Personal life As of 2020, Kentish-Rogers continued to reside in the family home where she was raised in The Valley. While reigning as Miss Universe Great Britain, Kentish-Rogers split her time between Anguilla and Birmingham.