The Unfinished,Unapologetic Becoming of Dee-Ann Kentish-Rogers

I didn’t grow up chasing crowns or standing behind podiums. I grew up barefoot in Rey Hill, Anguilla—running through bush trails, leaping off mango trees, dodging playful torment from older cousins, and learning that accountability can sting just as much as a scraped knee. My childhood was sun-drenched and sea-soaked, filled with the kind of moments that taught you resilience before you even knew the word. One minute, I was nearly drowning because I dared to jump into the deep end, and the next, I was being humbled by a splattered patch of okra I’d flung over my shoulder to escape dinner. Both moments, in their own way, shaped the woman I’ve become.

You see, life on a small island teaches you things big cities often forget. You learn to work with what you have, to be creative with limitations, and to carry yourself like you belong in every room—even if you’re the only one who looks like you. I’ve never asked for permission to take up space. I never thought I had to. Whether on a track, a political stage, or a global runway, I’ve moved with the unshakable belief that I am meant to be here. That belief has been both a gift and a lesson in staying grounded.

Today, when people list my titles—lawyer, athlete, beauty queen, politician—they often ask, “How did you manage all of that?” The answer is simpler than they think. Each of those paths was about service. Each one asked me to lead, to listen, to stand in uncomfortable truth. And at every turn, I’ve chosen the road that’s honest, not easy.

It’s difficult to place Dee-Ann Kentish-Rogers in a single box. And that’s precisely the point. As the first Black woman to win Miss Universe Great Britain, a Commonwealth Games heptathlete, a trained barrister, and an elected member of Anguilla’s House of Assembly, Dee-Ann has never followed convention. She embodies what it means to live “spherically in all directions,” a phrase she borrows from Fellini to describe a life that refuses to be linear. At just 32, she has already redefined what power, grace, and purpose can look like when fused by authenticity. But behind the accolades lies a woman deeply rooted in island life, unafraid of confrontation, and committed to building pathways for the women and girls who will come after her.

In this revealing interview, Dee-Ann shares the risks, reflections, and revelations that have marked her extraordinary journey—and the principles she refuses to compromise, no matter the cost.

TBWM: What was life like growing up in The Valley, Anguilla? Any childhood memories that still guide your steps today?

Dee-Ann: I grew up running around barefoot, climbing trees, and collecting countless bruises along the way. Life in Anguilla was all about family, fresh breeze, and the ever-present water surrounding our island. Being the youngest meant enduring the playful bullying of my three older cousins, which was somehow always fun in retrospect.

One memory that sticks out is a family beach day at Sandy Ground. As we were leaving, I thought, “One more dip wouldn’t hurt,” and I jumped into the deep end—and nearly drowned. That moment taught me I’ve always been prone to risk-taking, even though my family taught me caution. It’s a balance I still navigate today. Another was when my mom served cornmeal with okra—which I hated—and I tossed it over my shoulder, thinking I’d won the day and could skip off to the beach with my cousins. That was until she pointed to the column it splattered against. I learned accountability in that moment. Even now, I don’t shy away from it, no matter who’s watching.

Growing up in Anguilla instilled a deep sense of self-sufficiency. On a small island, you learn to be creative within limits. That resourcefulness still guides me through every challenge I face.

TBWM: What does it mean to you to be a Black Caribbean woman navigating global spaces like politics, pageantry, and law?

Dee-Ann: Honestly? It’s never occupied a pedestal for me. I’ve always just been myself. I never questioned my right to sit at big tables or needed permission to be the first Black woman to win a British pageant. I assumed I belonged—maybe that was a gift from my mother (thank you, Lorna), or maybe I’ve just always asked more questions of the world than of myself.

Being Black, Caribbean, and a woman shifts my perspective, but it doesn’t limit my ambition. These identities provide me with a unique lens through which to see opportunities for change. When I enter rooms—politics, pageantry, law, athletics—I’m not just representing myself. I’m carving pathways so others from similar backgrounds can see what’s possible.

TBWM: You’ve worn so many hats—lawyer, athlete, beauty queen, politician. What connects them for you?

Dee-Ann: Service. That’s the thread. Each role demands leadership, excellence, and advocacy—some on a micro level, others macro. But all require me to show up fully, with integrity.

I believe in living spherically—not confined to one identity or expectation. These roles express different facets of who I am. Living publicly has forced me to ask hard questions: What parts of me am I willing to compromise? What values are non-negotiable?

TBWM: What’s been your most defining moment so far?

Dee-Ann: In 2022, I stood firm on a controversial tax bill. The pressure was intense—from colleagues, constituents, powerful lobbyists, and even family. I stepped away from government for three days to reflect.

It would’ve been easy to step away for good and say it was for the people. But I knew I couldn’t live with myself if I chose personal comfort over public service. Returning—knowing the storm I was walking into—was the moment I truly understood who I am. That decision showed me I will always choose principle over popularity. It defined not just my leadership, but my character.

Dee-Ann Kentish-Rogers knows how it feels to have your identity split at the seams. Long before crowns or campaign trails, she was sprinting toward Olympic dreams with singular focus and fierce determination. As a teenager, she etched “Future Olympian” on her high school’s wall of dreams—a declaration that felt inevitable at the time. But life, as it often does, intervened with a plot twist that no training could prepare her for. An unexpected injury ended her athletic career before it truly began, tearing through not just physical capacity, but emotional certainty.

“The hardest part wasn’t just losing the athletic career,” she reflects, “it was losing the future I had so carefully mapped out. Who was I if not an athlete? What was my worth if I couldn’t compete?”

What followed was not instant reinvention, but a slow, determined reconstruction. The questions didn’t vanish overnight. But instead of sitting in the wreckage, Dee-Ann found a new track. She rerouted her ambition toward law, and later politics—both becoming new arenas for the same competitive spirit and drive. The athlete in her never disappeared; she simply changed races.

“Resilience isn’t about avoiding pain,” she says. “It’s about transforming it into something purposeful. That chapter didn’t end my story—it just forced me to write a different one than I had planned.”

What Grounds Her

In the whirlwind of public life, there is a quiet infrastructure holding Dee-Ann together—and it begins with her inner circle. In her most vulnerable moments, she leans not on institutions or accolades, but on the small community of close friends who remind her of her truth when the noise becomes too loud.

“They reset my narrative and my perspective. Because when the public is harsh, it’s easy to start believing you’re only what people say about you. My friends remind me of who I am.”

She also turns to the stillness of meditation and the ancient concept of equanimity. It’s become a vital tool in her emotional toolkit—one that teaches her not to suppress pain, but to stand inside it without being swept away. “It’s about standing steady in the chaos. Developing the capacity to witness hardship without becoming it. That’s how I stay balanced when defeat feels heavy.”

Though her life is stitched with high-stakes roles and sobering decisions, Dee-Ann is quick to remind us when asked about the last time she laughed uncontrollably or did something just for fun —“Every other day, honestly,” she says with a laugh. “When you’ve weathered serious storms, you start to find humor in the smallest things. It’s almost intoxicating.” Whether it’s paddleboarding and falling off more times than she can count, or simply choosing to laugh at herself, Dee-Ann makes joy a discipline. A ritual of release.

“Joy isn’t a luxury in this high-pressure life. It’s necessary. It keeps me light, human, grounded, and laughter is not an afterthought—it’s essential maintenance.

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