Firstly, thank you note to Mark Klecka, Sarasota’s real estate connoisseur and the power behind the "I Love Downtown Sarasota" Facebook group, for setting up this electrifying interview with Larry Siegel, owner of the legendary The Gator Club.
So, let’s talk hidden whiskey, jazz-filled nights, and a place that’s seen it all.
A Building with a Thousand Stories
The Gator Club, located at 1490 Main Street, has a legacy that few other buildings in Sarasota can rival. Built-in 1912 and designed in a masonry vernacular style, it was one of the first fire-resistant structures in downtown Sarasota, surviving a major fire in 1915. Known initially as Worth’s Block, it was one of the first brick buildings in the city. It features a classic brick façade with arched window frames on the second floor. At that time, the ground floor housed a general store, while the upstairs served as a residence for the Worth family.
As Sarasota evolved, so did this building. Over time, it transitioned into a mixed-use space with businesses below and residences above. A major renovation in 1928 modernized the structure while maintaining its historic character. Despite updates, it retains its original charm and now serves as a popular nightlife spot, preserving Sarasota’s architectural heritage.
During the 1920s, the space transformed into the Corner Cigar Store, which later became the Gator Cigar Store and Bar & Grill. It wasn’t just a casual hangout—it became a secret haven for bootleggers during Prohibition. Behind the staircase, a false wall concealed hidden compartments for bootleg whiskey—confirmed by Larry Siegel himself. During renovations in the 1980s, workers uncovered whiskey bottles stashed in cubbyholes, each labeled with a past patron’s name.
By the 1940s, the business expanded—it became a brothel upstairs. A madam’s cage, still visible near the back upstairs bar today, was used for transactions. Customers would ring a bell, summon the madam, and negotiate arrangements. The upstairs floor still carries remnants of its past, with small rooms that once housed working girls and their clientele.
Fast forward to 1988, Jay Foley took ownership and officially established The Gator Club as we know it today. Then, in 2005, Larry Siegel stepped in —not because he wanted to run a bar, but because he fell in love with the building itself. “I needed the bar to pay for it,” Larry laughs. “It wasn’t about business—it was about preserving history.”
Surviving the Highs and Lows
Larry first walked into The Gator Bar and Grill in 1973 but wasn’t impressed back then. “I took one look and thought, ‘This isn’t for me,’” he recalls. Yet, decades later, the same space became his passion. Initially, he planned to balance running The Gator Club alongside a restaurant, but fate had other ideas. A conversation with business broker Barry Seidel sealed the deal. It took nearly a year to finalize, but through determination and resilience, they made it work.
Despite the struggles and Larry's wife’s heavy illness at the time, the family pulled together. Larry worked seven days a week, while his daughter, Jamie, worked nights. His wife, Debbie, managed the bookkeeping and handled all the paperwork. In the early years, Larry worked during the day until about 2 p.m., then returned at 7 p.m. to close, repeating this routine three to four days a week. Jamie covered one day shift and four nights per week. After about a year and a half of training, their oldest son joined the business, eventually taking on night shifts on his own. A whiskey and tequila aficionado, he brought his expertise to the operation, further strengthening the family-run business.
Owning a bar is never smooth sailing. The 2008 financial crisis tested the business. Then came the pandemic, which forced The Gator Club to shut down for seven months. “We paid every employee—minimum wage, but they had something. PPP money helped, but most came out of pocket. We even sold whiskey barrels straight from the front door to stay afloat.”When Sarasota fully reopened, business skyrocketed. “We were one of the only open spots, and people flooded in. Some of our best years financially.”
Music, Whiskey, and an Unmatched Atmosphere
Music has always been at the heart of The Gator Club. When Larry took over, live bands played seven nights a week. "Ernie Ritz had four bands, with a DJ filling between sets. Some bands were great; some weren’t. Larry kept two—Chameleon and G-Force—but then revitalized the business over time by introducing fresher, more varied music while keeping it danceable.
The club features live music and DJs from Thursday to Saturday. Thursday nights are dedicated to reggae, while Fridays and Saturdays bring rotating dance bands that keep the energy high. Upstairs, DJs spin hip-hop and club anthems, while downstairs, the stage is alive with live performances, creating a seamless blend of two distinct nightlife experiences under one roof.
Let’s talk whiskey and tequila—because The Gator Club has nearly 400 whiskeys and 100 tequilas. “Variety is key,” Larry notes. “We’ve built one of the best selections in town.”
But beyond the drinks and the music, the people keep The Gator Club alive. Staff loyalty is unmatched—Johnny (32 years), Big Joe (20 years), and Carly (10 years). “We don’t have much turnover. Everyone earns well and has a work-life balance. That’s what keeps us strong.”
Upstairs has undergone several transformations—from a piano bar to a private club to a dance lounge. “One Friday night, I looked around and thought, ‘This space is underutilized.’ So, I told the DJ, ‘Let’s shift some furniture and add a second DJ.’ Three weeks later, it was packed. And it’s stayed that way ever since,” Larry says.
A Living Piece of Sarasota
Walking into The Gator Club is like stepping into a time capsule, but one that still knows how to throw a damn good party. The rich wood paneling, the glow of the antique bar, the hum of conversation, and the pulse of live music all come together nostalgically and electrically.
Larry puts it best: “What do we do for a living? We throw a party seven nights a week, and our staff are the hosts. That’s the secret.”
And as long as there’s music, good company, and a reason to celebrate, The Gator Club isn’t going anywhere.
Photos: iruphotos.com
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