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Longtime owner of Prosperity Social Club hands over operations to regular customer, fellow bar owner

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Posted at 10:32 AM, Jul 22, 2021

CLEVELAND — After 16 years running one of Tremont’s most well-known bars, Bonnie Flinner will step down as owner of Prosperity Social Club on Sunday and raise a glass to a new owner who hails from just around the corner at another Tremont bar.

When Will Hollingsworth, a longtime Prosperity Social Club regular and owner of The Spotted Owl Bars, heard Flinner might be moving on, his love of the tavern compelled him to act.

“Prosperity is my favorite bar in Cleveland,” says Hollingsworth. “I am as much of a fan of the Social Club as anyone out there, and I am excited to keep its history alive and momentum going.”

Flinner will stay at the bar for about a month to help transition the operation, even though she believes Hollingsworth won’t need much assistance.

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Bonnie Flinner standing in front of a chalkboard at Prosperity Social Club.

“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. “I’m delighted he will be bringing that energy, vision and experience to Prosperity.”

Flinner’s interest in the industry started as a teen when she began waiting tables at her aunt and uncles Parma Heights restaurant, Bit of Budapest.

Will Hollingsworth at Prosperity Social Club.

While bartending at Cleveland Heights’ Nightgown for more than a decade, the Syracuse University graduate started investigating and rehabbing area properties.

One day in 2005, she found a spot with lots of a potential—a cozy, wood-paneled Tremont barroom.

“My mother was Cleveland school teacher and my dad was a steelworker, so the history of this steel mill neighborhood and working class tavern—which the Dembowski family ran as Dempsey’s Oasis between 1938 and 2000—really spoke to me,” she said in a news release.

Flinner kept with the barroom’s retro vibe when she added breweriana decor, comfort food, speciality cocktails and a calendar of nostalgia-fueled commemorations like Dyngus Day, Supper Club and Prohibition Repeal, all of which have become events that Clevelanders look forward to every year.

When the decision came to find the next owner of her beloved establishment, she knew she had to find someone who appreciated old buildings and the soul of Prosperity.

“From our reverence for old buildings to prioritizing our teams, Will and I share many of the same values,” Flinner said. The Spotted Owl in Tremont is in the Union Gospel Press Building, while the Akron location occupies a former firehouse.

Hollingsworth looks forward to keeping an important institution up and running in Cleveland.

“We’ve built our success on listening to our spaces, being uncompromising in the experiences we offer and supporting our team,” says Hollingsworth. “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.”

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