What are your earliest memories of Kingston?

We moved to the Cayman Islands when I was six weeks old, but my father was very keen on me and my siblings having a Jamaican education. My initial return to the city, to visit my grandparents and other relatives as a very young lad, would be dominated by the memory of the Jamaica Flour Mills compound. I remember its towering structure always on my journey to and from the airport. Also, jaunts downtown with my late grandmother to sightsee around the Kingston Harbour, and go shopping where the Digicel building now stands, have always left their nostalgic mark. I would love, in my lifetime, to relive that free-spirited and prosperous downtown Kingston, at least one more time as an adult with my young daughter, Monroe.

What’s the most memorable meal that you have enjoyed in Kingston?

That’s very easy for me. I went to Swallowfield All-Age on Whitehall Avenue, and there is a restaurant there that remains, to this day, that is owned by a lady singularly called Norma. Although my mother always prepared Jamaican cuisine at home in Cayman, it was a luxury to have an abundance of things like curried goat, and stewed and fried chicken at one’s fingertips. I’m consistently exposed to fine dining and there are those that might say my palate is refined, but I truly have not been able to identify anything that comes close to the taste of that menu. Speaking of fried chicken, there is a notorious type that my best friend Ainsworth Wisdom’s uncle Wizzy used to make. I would give anything to taste that fried chicken again. I also have to mention Miss Vita’s cooking from my high school, Jamaica College. I love my mother dearly, but nothing compares to Miss Vita’s stewed chicken.

What would you do if you were mayor of Kingston for a day?

It would take more than a day, I must confess (laughs), but I would have to find a way to channel our natural passion and talent in a cohesive manner to eliminate differences and identify common grounds. Once such area is through the arts.

What would be your recommendations to a first-time visitor to Kingston?

The Bob Marley Museum, EITS Café, Screechie’s at Hellshire Beach, Strawberry Hill, Port Royal, Gloria’s, and Lime, and Maiden Cays. I really miss the wine bar Bin 26; hopefully, Christopher Reckord and the other principals will revive the brand or the concept in the near future.

What characteristics define a gentleman in the post-modern age?

The definition of a gentleman has nothing to do with your threads; it’s not your motor vehicle; and it’s not the size of your mansion, or your bank account. The greatest and most timeless substance of a gentleman is his legacy. I recently read somewhere that said, ‘Concern not yourself with your résumé that reads for your employment, but consider your résumé for your life after this’.

Is retirement something you consider a necessary — even welcome –stage of life, or has the concept become faded and archaic?

It’s outdated. Anyone over 30 or 35 years old has seen, through the lives of their parents, what loyalty has brought to the employer; they’ve seen what pensions have squandered; they’ve seen the stress that commitment to one’s job has placed on marriages or unions; and they’ve seen the rising cancer rates in the region. This generation is a lot more alert, more aware, and they possess better access to information. We aren’t depending on a magical silver lining after the age of 70 or 80 years old. Now is life; and life is now.

As a legal mind, what will be the next just-over-the-horizon issue to face the Caribbean community?

The issues are more immediate and more urgent than we may think, and that is of securing LGBT rights and wider human rights for our citizens. Our people will continue to be unable to realise their full potential until we get serious about the discussion surrounding equality. A lot of people don’t like to touch the topic, but colour discrimination is another very disturbing practice that we need to get resolute in putting a stop to.

The Jamaica Observer Table Talk Food Awards has now entered the Cayman Islands’ culinary landscape. As an inaugural judge, how do you see the event shaking things up in your neck of the woods?

It’s been a well-received component. We have had at least half-a-dozen judges, including myself, come over from Cayman to attend the Jamaican edition of the Foodie Seminar and Awards itself (held on Wednesday and Thursday, respectively). We love food, but the Food Awards will now focus our attention on the real faces and stories behind the exquisite dishes and the glossy dining experiences, which is what already pertains here in Jamaica.

What do you think is the Caribbean’s business identity, and what value lies in its allure?

I believe our identity is our relaxed persona. People are coming here for obvious reasons: tropical weather, sandy beaches, and we’re easygoing. I’ve seen the people in international cities: They’re anxious. They’re stressed. Sometimes, we are persecuted for being lazy and unmotivated, but we’ve been blessed with a vibrancy that lends itself to business and integration, and which keeps people coming back to our shores. It’s very important that we never lose sight of that.

Share some places in your travel black book.

My absolute favourite place on the planet is Barcelona, Spain — that’s where my wife Caroline and I got married. The Jamaica Observer did a very wonderful spread on that, which I go back and read from time to time. The remarkable Italian cities of Rome and Venice. London will always be central to my existence because that’s where I did my bar studies. I do like San Francisco, and the Napa Valley wine region. My best friend’s 30th birthday celebrations at a very extravagant villa there still remain a highlight. I just came back from Havana, Cuba, — go there, ask for the bartender Odel at the Saratoga Hotel, tell him Richie sent you. You’ll have a wonderful time, and he’ll gift you with a cigar.

What do you consider your best and worst traits?

My worst traits I would chalk up to be procrastination and overanalysis. My wife evens me out. My greatest attribute, I’ve been told, is my compassion.

What was your last major splurge?

The beneficiary of that will be my wife, and let’s just say I don’t want to declare the proceeds (laughs)!

What is your philosophy?

Talent suppressed or denied is opportunity lost; and I believe nepotism is the evil of success. No matter what you do, always rely on merit; merit should ultimately define us.