A member of the Anguilla Progressive Movement, Kentish-Rogers has served as the Minister for Education and Social Development in the government of Ellis Webster since 2020.

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.

[3][4] 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.

[11][12][13] 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.

[15][16] 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.