Tremont’s Prosperity Social Club Changes Hands

Bonnie Flinner has passed the torch.

Flinner, who started working in the hospitality business as a teenage working in a family-owned restaurant, had been bartending at Nighttown in Cleveland Heights for more than a decade when she decided to go into business for herself, and, in 2005, she purchased the venerable Dempsey’s Oasis in Tremont (opened in 1938) and re-christened it Prosperity Social Club.

She turned it into one of the hippest hangouts on the west side, with high-quality comfort food, specialty cocktails, interesting music and special promotions such as Lenten Fish Fries, Dyngus Day and prohibition repeal parties.

But she’s put in her time and was casting about for someone who could take over and respect the place’s tradition. And, on July 25, she handed the place over to Will Hollingsworth, owner of the Spotted Owl in Tremont and Akron.

“I’ve known Will for a while now, and I’ve watched him move from being a bartender at Lolita to opening his own bar concept in multiple locations,” says Flinner. “From our reverence for old buildings to prioritizing our teams, Will and I share many of the same values.”

Adds Hollingsworth, “We’ve built our success on listening to our spaces, being uncompromising in the experiences we offer and supporting our team. So the opportunity to add the Prosperity team to our company, while protecting what I really feel is a Cleveland cultural institution, is a really exciting honor.”

Flinner will be sticking around for a month to help with the transition so you can stop in and wish them both her and Hollingsworth well.

Prosperity Social Club

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