A former Bucs cheerleader just won Mr. Continental, one of the world’s biggest queer pageant titles

Lorenzo Gilbert is used to making history, and he’s not stopping anytime soon.

Gilbert, 38, made headlines as the Tampa Bay Buccaneers’ first male cheerleader in 2019. Under his stage name, Isaiah Sanchez Hilton, he made headlines again this month when he was crowned Mr. Continental 2026.

The Continental Pageantry System, one of the world’s most prestigious drag competitions, crowns its royal court each Labor Day weekend in Chicago.

This year’s pageant also included a tribute to late Tampa drag queen and Puerto Rican trans icon Jasmine International by Alexis Mateo, Miss Continental Elite and a RuPaul’s Drag Race star who got her start in Tampa. International, who went by Jasmine Jimenez offstage, died at 46 years old last month.

Though Miss Continental and the Plus and Elite counterparts are drag queens, the Mr. competition is for cis male performers. But the competition is still treated like drag. Gilbert has a performing family and a son who has followed in his footsteps as a Bucs cheerleader.

Gilbert’s “gay grandmother,” Valencia Santiago, unlocked pageantry for him. Two years before competing, he performed at Continental weekend as her backup dancer. While practicing choreography, Continental owner Jim Flint spotted him.

“As I was leaving the stage, he told me, ‘I can’t wait till I see you on this stage,'” Gilbert told Creative Loafing Tampa Bay. But at the time, he had no desire to invest as much time into pageantry as the ladies.

“I mean, they spend sometimes thousands of dollars. And I was, like, 19 years old. I’m not spending that kind of money on pageantry. I was spending on shoes, and food and video games,” Gilbert added. “But somehow those words convinced me that I was meant to be on that stage.”

Now, Gilbert— a Miami native who’s now lived in Tampa for 15 years where he works as a dancer for Tampa-based Event Show Productions—is the first man to simultaneously hold both Mr. Florida and Mr. Continental titles.

Gilbert, who has been competing in pageants since 2008, beat 13 of the nation’s best male entertainers in runway categories, including swimwear, formal wear and a Q&A. His solo performance was a Broadway and ’60s dance number.

The win marks his comeback from a low period. Although he’s been consistently successful in the pageant world, Gilbert didn’t make the Bucs team the year after his historic season.

“When I tried out the second year, I was a little discouraged,” Gilbert said. “I couldn’t pinpoint why, because I had such a good year, but it just seemed like the energy wasn’t there for me. Something was missing. “

Gilbert had fallen in love with cheering and football, but it wasn’t enough.

“I did want to be a part of the team, because I had invested so much the previous year, and I was emotionally invested,” he said. “I just felt like that dream was taken from me.”

Gilbert recalled suffering from depression, which contributed to him dropping out of tryouts the following year.

“I felt at that moment that if I gave it my all again and I received no, that it would really break me,” he said.

He’s focused on the things that make him happy, like dance and pageantry. But there’s still hope for him to return to the field. He’s thinking about trying out again as he watches his stage son, Kamarion Lavish, cheer as one of seven male members on this year’s team.

“I’m so proud of him,” Gilbert said. “So there may be a spot for me on the team next year. Who knows? “