“I Don’t Just Win, I Conquer”

Meet Didi Winston, a Bajan trans pioneer, LGBTQ activist, and flag-waving champion.

Collage of photos of Didi Winston.
Photo illustration by Lisa Larson-Walker. Photos by Didi Winston, Ro-Ann Mohammed, and Belle Holder.

This piece is part of the Legacies issue, a special Pride Month series from Outward, Slate’s home for coverage of LGBTQ life, thought, and culture. Read an introduction to the issue here.

Flag-waving at Carnival is a Caribbean art form steeped in tradition, with flag-bearers sometimes referred to as “the forgotten soldiers of the steel pan world.” To win the competition at Barbados’ annual summerlong Crop Over festival, a flag-waver must make “the most spectacular use of the flag” in leading the charge of the band. In this role, as well as many others in her life, Didi Winston is usually out front and center.

Winston is the first transgender woman entertainer Barbados has ever known. A trained dancer who performed at the popular Plantation Garden Theatre Dinner Show for years, a makeup artist for the Caribbean Broadcasting Corp., and a multiwinner (20 times!) of the Winston Jordan Flag Person of the Year Award, Winston recently parlayed her movement expertise into running a fitness class. For $50, get five weeks’ worth of one-hour sessions, so you too can learn how to “wuk-up” (Bajan for a local gyrating dance move) and wave to the pulsating soca beat. Flawless legs like Winston’s are not guaranteed.

Right now, Didi is busy prepping for Crop Over’s big finale (Kadooment Day on Aug. 6) and rehearsals for the upcoming Pride parade (June 30), all while working as an Inglot cosmetics artist. Over brunch, we discussed her schedule, mad skills, and how she’s fighting to leave a legacy of stronger LGBTQ rights for the next generation with the cunning use of flags.

This interview has been edited and condensed for clarity.

Falene Nurse: To the uninitiated, what is flag-waving?

Didi Winston: Flag-waving is an artistic expression of movement. For me, it’s more than “flagging and wukkin’ up,” it’s about freedom. It dates back to the first Carnivals in Trinidad, when the flags were much larger, as the purpose of the “waver” was to clear a pathway through the crowd. The “flag-bearer” usually had a confident stage presence. They had to be commanding yet graceful, to enthrall a crowd. Isn’t that amazing? Now flags have been watered down in size, but I like to, you know, throw in a bigger flag, maybe more than one. When I mix it up, the crowd goes wild!

Flag-waving in Barbados is a competition during Crop Over, which you have won multiple times. How are you judged?

Well, you have to be a good dancer, and that’s my background, so if a split is needed, hunty. … But the NCF [National Cultural Foundation] uses a point system and a whole set of criteria regarding presentation, technique, and crowd response. I started competing at 18, and now I’m 28 [laughs loudly]—here we are.

So competition is something you did, before, during, and after transitioning?

Oh yeah, absolutely. The outfits change, granted, but truth be told no one remembers me from before. So each year I had to get better. And then I won, and I realized, “Wait, you win money? Why wasn’t I told!” But in all seriousness, it was never really about the money. You do it for the people, to keep the art form alive, and the fact that it’s a Bajan trans woman representing and contributing to the culture. That’s important.

Was the local response supportive?

For the most part, yes. And those that don’t [support me] weren’t in my “sphere” anyway. People know me for flag-waving, so if someone needs to get educated on other things, I can do that, too. I was once asked, “What’s it like to be a transformer?” I’m not a robot in disguise, but this wasn’t an insult, she was very old and didn’t have a clue about the right language. So I explained, “I’m Didi Prime.” [Laughs.] No, I said, “Ma’am, I’m Didi Winston, I’m a transgender WOC [woman of color].” She apologized and was grateful for the knowledge. But no, not everyone is that nice.

How did your parents react when you began your transition?

My parents always knew because if they didn’t know, honey, they were blind! My parents, my sister, all wonderful, but I tell you the day that my dad introduced me as his daughter, I cried. And bless him, he didn’t even know why. I hugged him and went on my way.

Now you’ve turned flag-waving into a successful fitness class?

Well, it tones the leg muscles and arms. People see me out there, and they want to have a go, but there is a learning curve. Then they feel it, dahling this is an actual work out. It’s also a tradition I like to teach to the next generation. I don’t want flag-waving to die off here in Barbados.

Not to make you the spokesperson for all queer people of color everywhere, but do you find because of our history that being queer and black is treated as a betrayal? 

Look, I appreciate the context of slavery, but same-sex relationships go back to ancient Africa. So I feel that unhealthy remnant [of homophobia] needs deletion, like colorism. Eradicate both from all communities of color.

Do you feel we have progressed in the Caribbean as a whole, considering what is happening in Jamaica?

I can only speak to my experiences. For us, our first female prime minister has been pro-LGBTQ for the most part. No shade to Jamaica, but our community there needs bombs and guns. That is my wish for every Jamaican gay woman, male, and transgender person. We need to protect ourselves, turning the other cheek won’t keep you alive. You threaten me with a bottle, hunty. I’ll introduce you to the next passing bus.

But the problem’s not just Jamaica. Two trans women of color (Chynal Lindsey and Muhlaysia Booker) were killed in Texas recently.

That’s one thing in Barbados, yes, I’ve been threatened, but that level of extremity cannot happen in a nation of 270,000 people. The community is too small; there will be repercussions, whether legal or otherwise. We don’t play that. That being said, I wish the police reacted faster when there are incidents.

Didn’t you meet with the police about sensitivity training within the LGBTQ community here?

Yes, but sensitivity training in general. A lot of positive discourse came from that meeting, a lot of education, so it was all good. But sometimes it’s common sense: If you don’t know the correct pronoun, maybe start by asking a person’s name? Also, if a prostitute reports a crime, “Hey, Mr. Police Officer [face of utter shock and horror], rape and physical assault is not part of the job!” I advise, “Don’t let ignorance get in the way of doing your job. Do your job. That is all.”

So you were heavily involved with Pride Barbados last year. Will you be doing a parade again this year?

Yes, it was our first, and we had no problems. But I wish we had stronger numbers.

There are gay fetes (parties) and gay nights, but no gay clubs here, right?

I know, when I get the coins I’m opening a club—Glitter. A party, a safe space, and a place of leisure and relaxation. Three floors, one for each mood. Hah! Everyone is welcome, but it’s a queer club.

Is it true the Pride parade started at Rihanna Drive, and if so, why?

Well, she is an ally, but honestly, it was one of the few places that everyone knew where to go. Locals and tourists alike.

Rihanna is considered an international LGBTQ ally, but do you ever wonder why she isn’t more vocal here?

Imagine, a Bajan is a gay icon. Rihanna is a source of real pride here. But I do wonder if she’s aware of how things are for our community? A lot of people don’t even know that the Sexual Offences Act is still law! Ri Ri might just need an update.

It could be that simple.

No need for the Bat-Signal, but get word to Capt. Fenty! [Laughs.] Something tiny would make a huge impact. Maybe jumping with a rainbow flag?

That would be nice.

Hip hip Hooray.

Is there any campaign to abolish the Sexual Offences Act?

Our prime minister, Mia Mottley’s party platform, called for a referendum on LGBTQ issues. As attorney general, she commissioned a study on laws that affected HIV interventions. The study recommended scrapping the anti-sodomy law.

What is your hope for LGBTQ life in Barbados?

To be stronger, to grow, and to be free. To feel entitled to show simple acts of affection in public. There are couples here, been together for 50 years. Never walked on the beach hand in hand, can you imagine?

[Winston tears up for a moment.]

You know my baby godson said the most innocent thing. He said, “Auntie, you can eat this because it says, ‘No trans fat.’ ” Thinking it couldn’t make me fat. So that’s the next Bajan generation. Gurl.

What are your plans for Crop Over this year?

Having a blast. Flagging and jumping.

Planning to win?

Always winning, hunty. But I don’t just win, I conquer. [Purrs.]

Read more of Outward’s Legacies issue.