Gassy Winds reflects on the Queen Mother’s important, year round role in Key West.

Let’s play word association. If I say “drag queen” you say what?  Big pink wigs? Of course! Cher? Sure. Sexual innuendo dovetailed into biting sarcasm?  Yes, and yes. But how about charity and philanthropy and tireless fundraising? These traits are just as true as the more outlandish stereotypes drag divas are associated with, but a lot less familiar.

That is the case here in Key West as it is the world over.  In fact, I am learning that Key West has more than its fair share of drag-helmed events geared toward helping individuals and organizations in need. For me this comes as no surprise.

Historically drag queens have always served the dual role of performer and activist, often on the front line of all the significant LGBT battles for equality. But it doesn’t stop there. The drag community has donated innumerable hours raising money and consciousness for the sake of a variety of causes.

Take the Queen Mother Pageant for example.  Now in its 31st year, I met its outgoing Queen Mother, Gassy Winds, aka J.B. McLendon poolside at a local resort.  McLendon described the Queen Mother Pageant as the crème de la crème of Key West pageantry, and then proceeded to list half a dozen other similar events that take place on the island.

“Every pageant in town is connected to one charitable organization or another,” Gassy told me.  But it’s not just the one organization that benefits from the Queen Mother Pageant. The reigning Queen Mother becomes a kind of Goodwill Ambassador for all local charities.

As far as the Queen Mother Pageant is concerned, the pageant itself is a fundraiser for the Visiting Nurse Association and Hospice of the Florida Keys.  The winner gets a crown and truckloads of glory of course, but they also have a job to do. This past year Gassy Winds participated in 31 local events in support an array of other local organizations. And when I say support I mean financial support and we’re not talking nickels and dimes.

“We raised $20,000 in two hours for the Studios of Key West”, Miss Winds bragged, and “$225,000 in total for the year when you combine all 31 functions.” That’s a lot of money but it’s also a ton of make-up and at least 100 hours of volunteer service!

I asked Miss Winds what kind of gumption it takes to enter the show.  Gassy took a swig of her virgin bloody mary, sat back and reflected upon her own journey.

“Well,” she said. “I made my first run at the crown in 2009, two years after moving to Key West. I spent six weeks in preparation but did not win; I ended up first runner-up. Then, in 2013 I received the Humanitarian of the Year Award from AIDS Help.  I spoke to my mother and she said it was time to try again. By then I had four years of contemplation under my belt. I decided to do it. I spent $3,000 on a new set of gowns, entered and won. The rest is history.

The two-hour pageant to replace Gassy Winds will take place at La-Te-Da on Monday, May 12. In that time, four to eight contestants will compete for the crown of Queen Mother XXXI. They will sashay before VIP guests and a standing-room-only crowd showcasing their talents, and their intellectual prowess in a formal Q&A. One might even lip-synch to Cher in a big pink wig.

If you’d like to witness this year’s history being made and help support not just one but many local charities, then go to to secure your seat at the pageant.


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