Spotted Owl's Will Hollingsworth Buys Prosperity Social Club in Tremont, Plans to Keep His 'Favorite Bar in Cleveland' the Same

click to enlarge Prosperity Social Club is changing hands, but not changing anything else - COURTESY PROSPERITY
Courtesy Prosperity
Prosperity Social Club is changing hands, but not changing anything else

As Prosperity Social Club owner Bonnie Flinner started planning her exit strategy from the Tremont bar and restaurant she'd owned for 16 years, she didn't have to look far for someone she knew and trusted to hand the keys to.

That person is Will Hollingsworth, who has been running his own bar down the street and perching himself on Prosperity's bar stools for years.

“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.”

Hollingsworth, the owner of the Spotted Owl in Tremont and Akron, cherished the opportunity to make sure the bar he's long been a regular at lives on.

"I have never been shy about sharing my affection for Prosperity Social Club with anyone," he says. "I am protective of a place that means a lot to me and to other people. We won’t change anything until we need to. Prosperity is my favorite bar in Cleveland. 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.”

click to enlarge Hollingsworth at the bar - COURTESY BONNIE FLINNER
Courtesy Bonnie Flinner
Hollingsworth at the bar
The sale will officially close on July 25th, though Flinner will stay on for a month to assist in the transition.

Flinner put her heart and soul into Prosperity, turning the old Dempsey's Oasis, which closed in 2000, into the cozy, retro concept that became one of the most beloved joints in Cleveland. Hollingsworth doesn't take that lightly, and wants Prosperity to keep being Prosperity.

“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.”

For Flinner, the exit was necessary but nevertheless bittersweet, especially after keeping the business afloat during the pandemic.

Courtesy Bonnie Flinner
"With the patronage and generosity of our customers and neighbors, our employees were able to make a living," she says. "Today I believe Prosperity is stronger and more vibrant than it has ever been. I believe our current staff is killer and the best combination of talent I have ever encountered. I think Will is taking over at a time of upward momentum and is positioned for success. I am extremely grateful to everyone over the years who helped to create an inclusive, communal space where memories are created and milestones celebrated. I will miss it every day, but I am looking forward to being on the customer side of the bar, on a tall stool next to a familiar face, sharing laughs and camaraderie.”
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