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This Week in Jacksonville: Business Edition

  • May 21, 2026

JACKSONVILLE, Fla. – Darien “Jack” Jackson says his new Dapper D’s concept is ready to open in Downtown Jacksonville’s Elbow district—nearly a year later than he originally expected.

“We had our plans ready in July, and they didn’t get approved to November,” Jackson said, calling permitting the first major hurdle.

The former 11 Ocean space is now a two-level operation: cheesesteaks downstairs and a cigar lounge experience upstairs.

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“I didn’t just open up a cigar lounge,” Jackson said. “I opened up two businesses at one time.”

Jackson said contractor problems also stretched the timeline, including a dispute that led to litigation.

“It got to a point where the contractor just wasn’t providing the product… It wasn’t the quality that we needed,” he said. “Time is money.”

On the menu side, Jackson is making a straightforward promise: an “authentic Philly cheesesteak”, made without shortcuts.

“We cut no corners,” he said.

And for other entrepreneurs considering downtown, he offered both encouragement and a warning about the grind.

“Downtown Jacksonville is growing,” Jackson said. “We need you downtown… You need perseverance, you need temperance, you need fortitude.”

Copyright 2026 by WJXT News4JAX – All rights reserved.

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