Sophie Bolich

Caribbean Restaurant Proposed For Center Street

Jerkin' Me Crazy would showcase island cuisine with a soul food twist.

By - Aug 21st, 2025 01:32 pm
Photo taken May 17, 2022 by Jeramey Jannene. All Rights Reserved.

Photo taken May 17, 2022 by Jeramey Jannene. All Rights Reserved.

A new restaurant, Jerkin’ Me Crazy, is slated to open on the Northwest Side, bringing Caribbean flavor to a formerly city-owned building at 4704 W. Center St.

The venture, from restaurateur Darryl Simmons, promises more than just Jerk chicken—it aims to be a source of positive change for the community.

“I just want something that the people can look at and call their own, and feel proud of,” Simmons said. “I hate to see so many dilapidated buildings throughout these areas, and I just feel like we should have more people investing, creating jobs, creating opportunities.”

For his part, Simmons is revamping the 1,400-square-foot Center Street space, formerly a childcare center, with a full renovation and kitchen build-out. Interior work is approximately 80% complete, he said, noting plans to update the building’s facade and windows as a final step.

The future restaurant will occupy one of five commercial stalls in a building the City of Milwaukee acquired through a 2015 property tax foreclosure. Simmons said four additional tenants—including a juice cafe—are already lined up for the remaining stalls, with plans to coordinate their openings if possible.

An experienced restaurateur, Simmons’ previous ventures include a Memphis barbecue spot and Bellagio Soul Food which operated at 8665 W. Brown Deer Rd. The latter closed down amid Simmons’ recovery from an accident, he said.

Jerkin’ Me Crazy will combine Simmons’ earlier experience with his Belizean roots, offering Caribbean cuisine with a soul food twist. “That’s really my strong suit—jerk chicken, curry chicken, stew chicken,” he said. “I’ve got a lot of Belizeans in my family, so I kind of grew up in that community.”

Additional menu items could include Simmons’ specialty Jerk chicken dressing, steamed cabbage, baked macaroni and cheese, candy yams and pork chops. He also plans to serve Caribbean-inspired cocktails and beers.

Along with food and drink, the restaurant hopes to feature live music including jazz and reggae bands.

As chef and owner, Simmons said he’s glad to have control over pricing and is committed to keeping meals reasonable for neighbors. “What I want to bring to the community is a safe place where families can come and dine,” he said. “I can offer an affordable dinner with love and just put some smiles on the faces of the people in the community.”

A license application for Jerkin’ Me Crazy is pending before the Milwaukee Common Council. Simmons aims to open in October, but said the finalized date will depend on permit timelines.

If approved, the restaurant’s proposed hours of operation are 8 a.m. to 11 p.m. daily.

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Categories: Food & Drink

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