Dwayne A. Caines was born in Bermuda in 1970. He began his education at the Prospect Primary and continued his secondary education at the Warwick Secondary later moving on to Bermuda Institute where he graduated in 1988. He received a Bachelor of Arts Degree from Oakwood College and did his graduate work in Public Relations at Wayne State in Detroit, Michigan. Mr. Caines was employed as the Public and Media Relations Manager for the Bermuda Police Service for 18 years. He is a community-focused gentleman who enjoys working with young people, with a determination to empower them to become active in their communities and advocates for social change. In May of 2019, Caines became the Chief Operating Officer and Secretary of the Corporation of Hamilton (City of Hamilton). He is married to Roshanda and has three girls Deshay, Dasha and Dori.


1. What is your favorite Bermudian tradition?
Cup Match in Somerset is my favorite time of the year. I love every aspect of the two-day experience. Fire bun St Georges, may a thousand stinging nettles invade the scalps of all St. George’s fans.


2. Where is the best place for a fish sandwich?
LITT, they have local fish on order. They also have cool staff and a great atmosphere.


3. Where is the best place for sushi?
Harbourfront — they are amazing for both service and product.


4. What’s the most Instagram-worthy place in Bermuda?
The Railway Trail in Paget, when the natural light peaks through the canopy of shade created by the overgrowth of trees — that view as you walk is breathtaking.


5. What is the best advice you’ve ever gotten?
To thine own self be true.


6. What do you like most about yourself?
My love for helping others, and the mole in the center of my back. Oh and my crooked finger on my right hand, and while I am at it, my off centered right eye. You did say like, right?


7. What do you like least about yourself?
My flat feet and the bald spot that is getting larger every time I come from the barber (he is doing it on purpose).


8. What keeps you up at night?
Acid reflux lol oh, and overthinking decisions, and conversations. Also, my daughters when they are home for breaks, as I wait for their bikes to come into the yard… (the best sound is their bikes coming into the driveway).


9. What’s the biggest obstacle you’ve overcome?
Cancer — two years cancer free (Bermp Bermp).


10. What’s your favorite thing to do on Sunday?
Walk on the Railway Trail, then a codfish breakfast.


11. How long have you been in Bermuda?
I was born here, I left for University and Grad School and I lived in NYC for 3 years (1998-2001), but for the most part Bermuda has been home.


12. What’s your favorite beach?
Grape Bay, I walk on it at least 5 times a week.


13. What was your first job ever?
Delivering newspapers for The Royal Gazette. I still remember my route — one of the houses is now the US Consulate.


15. Who was your favorite teacher as a child?
Mandell Hill, he was a history Teacher at BI. He started teaching at 21 and was a sharp dresser. He loved Bermuda, sports, and history. Sadly he has passed. He was my oldest daughter’s godfather.


17. Who was/is the most influential person in your life?
My mother, she believed in me before I believed in myself, and she set a standard for achievement, belief and service.


18. What’s in your wallet right now?
4 access cards to various places in the COH, $200 credit cards, health cards, business cards, an old button, and a key.


19. Do you ever get island fever?
All de time (I just get on a plane and cure it).


20. What’s your favorite thing in your office?
My little fridge under my desk.


21. What’s your favorite thing at home?
My family.


22. Loquat or Bermuda banana?
Loquat, I love the hunt and collection of them and the taste — I love the sour ones.


23. St George’s or Somerset?
What kind of question is that? The only team in Cup Match SOMERSET!!!!


24. Cricket or football?
Football, love the beautiful game.


25. What are you reading right now?
Dare to Lead by Brené Brown.


26. What podcast are you listening to right now?
Revisionist History with Malcolm Gladwell, Season 4.


27. What is your guilty pleasure?
Salt and Vinegar Pringles chips.


28. What is your biggest phobia?
“Liar” phobia.