Plans for The Greenleaf basement speakeasy took a figurative, perhaps even a literal, step with owner JWB Real Estate Capital’s request for city approval to build exterior stairs at the historic Downtown building.
The stairwell is designed to descend from the sidewalk on Adams Street into the speakeasy in The Greenleaf’s basement.
The city is reviewing a permit for contractor Avant Construction Group to build a basement shell and exterior stairs at 200 N. Laura St. at northwest Laura and Adams streets.
Avant indicates a project cost of $350,000. Studio 9 Architecture is the architect. Both are based in Jacksonville. Codes-ABC Inc. of Orange Park is providing private plan review.

The notice of commencement filed with the city specifies the work as build-out of a basement shell and construction of exterior stairs.
JWB Real Estate Capital President Alex Sifakis said April 14 that the basement of The Greenleaf extends 10 feet under the sidewalk on Adams Street.
“So we are cutting a hole in the sidewalk and installing a subway style stair that will go down to a speakeasy/jazz bar,” Sifakis said.
He said JWB doesn’t have a timeline or operator for the speakeasy and jazz bar but that it likely would be Steve Palmer, who will operate the Oak Steakhouse of the ground floor of The Greenleaf where Jacobs Jewelers had operated.
Palmer is founder of The Indigo Road Hospitality Group. Sifakis said previously an early 2027 opening is expected for the restaurant.
Sifakis said April 14 there will be project construction coordination with the Downtown Investment Authority and with the city Department of Public Works on the sidewalk project.
Sifakis said in February the speakeasy would be built-out in 3,500 square feet of space that was formerly used as a shopping area for VIP customers of Jacobs Jewelers.

JWB Real Estate Capital christened its resurrection of the 12-story property Feb. 23 during a ceremonial opening of The Greenleaf, its new headquarters.
“One of the reasons we wanted to bring our offices down here is that we believe that having our offices Downtown is going to help us attract the best talent so that we can continue to grow our company and grow the city,” Sifakis said during a ribbon-cutting for the building at 208 N. Laura St.
While the general address is 200 N. Laura St., the building’s entrances also are addressed as 204 and 208 N. Laura St.
JWB Real Estate Capital bought The Greenleaf, then known as the Greenleaf & Crosby Building, in 2022 for $7 million and spent $17 million renovating it, Sifakis said. JWB moved its offices into the building Feb. 2 from its previous Southside headquarters, bringing 120 workers Downtown.
As with JWB’s other historic restorations, Sifakis said the developers ran into unseen challenges in revitalizing The Greenleaf.
“The degree of difficulty for this one was probably like a 7 (on a scale of 1 to 10),” he said, based partly on the scope of the 66,000-square-foot project and the height of the building.
“We had to put in new elevators and bring them down to the basement. There was a 100-year-old water barrier that caused a bunch of issues. There are things you find in these buildings, and it never stops. They’re always over budget. It’s critical to have the city and the Downtown Investment Authority as a partner … because we run into so many issues on these older buildings.”
The Downtown Investment Authority approved a $4.97 million forgivable loan package in August 2023 for the project.