As Alex Sifakis led visitors on a recent tour of The Greenleaf, the Downtown headquarters of JWB Real Estate Capital, the complexities of restoring the historic building revealed themselves at numerous turns.
Sifakis is president of JWB, which spent $17 million resurrecting the 12-story building after purchasing it for $7 million in 2022. The Greenleaf, also known as the Greenleaf & Crosby Building, reopened in February with JWB offices across five floors.
Sifakis said revitalizing the building meant overcoming challenges throughout the structure and even below it, including an unanticipated and extensive project to replace plumbing drains below the basement floor.
JWB’s investment stretches well beyond the building’s functionality, as the company also is incurring significant expenses in restoring details. Those projects include sourcing a match for the marble in the lobby, a portion of which is being replaced after being removed years ago to make a doorway.
Another example is the ornate, recessed ceiling in the space formerly occupied by Jacobs Jewelers on the southeast corner of the building, which is being built-out as Oak Steakhouse by Charleston, South Carolina-based Indigo Road Hospitality Group.
Jagged holes dot the ceiling, where workers broke through the original molded plaster to hang supports for a drop-tile grid and the air-conditioning system during the 1960s and 1970s. Sifakis said the dozens of holes will be repaired through a process that involves casting new pieces from molds of the original designs.
Bryan Moll, a partner with JWB in the Gateway Jax development Downtown, said Sifakis’ appreciation for historic preservation helped attract him to Jacksonville after leading such developments as Tampa’s Water Street and the Amazon HQ2 National Landing site near Washington, D.C.
Moll, JWB and partner DLP Capital are nearing completion of the first building in Pearl Square and have topped out a second, with plans to invest more than $750 million across 10 projects.
“Alex’s passion for Jacksonville in general but for Downtown in particular is one of the reasons I took this job,” Moll said.
“Where the passion lies is really from such an inspiring place. He wants to make Downtown and the urban areas of Jacksonville better so that when his kids go to college, they’ll want to come back.”
Restoring Downtown
Sifakis and JWB have been involved in several adaptive reuse projects Downtown, including the former Federal Reserve Building at 424 N. Hogan St. ($6.5 million); the neighboring Florida Baptist Convention structure at 218 W. Church St. ($9.5 million); the Porter House Mansion at 510 N. Julia St. ($1 million); and the Downtown Seminole Club, now Sweet Pete’s Candy, at 400 N. Hogan St. ($600,000).
In February 2024, Jacksonville City Council approved $4.9 million in incentives for the Greenleaf project.
Today, JWB occupies floors two through five of the building, plus the top floor.
The 11th floor is the only space unleased, with other tenants being Shelly, Middlebrooks & O’Leary Inc. specialty insurance on the sixth floor, Southern Strategy Group on the seventh, Regus Jacksonville on the eighth and ninth, and TruTechnology Business IT Solutions on the 10th.
HiReformance Institute operates a Pilates studio on the ground floor. The Oak Steakhouse space is being prepared for build-out, with the city reviewing a permit for the project at an estimated cost of $2.95 million.
Plans also call for a basement speakeasy and jazz club in the former VIP space for the jewelry store. That project will involve creating a subway-style staircase near the building’s southeast corner.
JWB’s spaces are designed with an open concept, including a column-type staircase connecting the main floors. The company operates a kitchen and pantry that provides free meals and snacks to the 105 employees who work at the headquarters, plus a gym with weights, exercise bicycles and other equipment.
The gym also features a plant-covered living wall that serves as a design element and a natural air filter.
The 12th-floor meeting and conference room includes a basketball floor with a regulation hoop. Other design elements include a set of swings along the north-facing windows, where visitors can enjoy a view of City Hall, Gateway Jax’s construction projects and other sights.
A podcasting studio is nearing completion in the basement, where space for the speakeasy is being cleared. Challenges related to that project include repairing patches of the ceiling that are below the sidewalks along Laura and Adams streets and are leaking after years of neglect.
‘Pretty remarkable’
Sifakis said his interest in the building was driven partly by his belief that Downtown will become the community’s magnet for drawing talent as more historic redevelopments come on line and projects like the University of Florida’s graduate campus take shape.
He said Downtown offered JWB the best positioning to attract highly capable employees.
But beyond strategic business reasons, Sifakis conveys an appreciation for historic preservation in describing his interest in The Greenleaf. It shows in his admiring comments about the building’s Chicago-style architecture, his plans to convert a hand-operated elevator to the basement for the speakeasy and more.
Take the ceiling in the Oak Steakhouse. Sifakis said that when he was considering buying the building, he crawled into a space between walls to see if the original ceiling was still in place and to gauge whether it could be saved.
When he saw that it could possibly be salvaged, he said, its beauty and the opportunity to bring it back to its original condition helped convince him to make the purchase.
Moll said Sifakis’ level of care and attention to Jacksonville’s historical structures helped him become a leader in the effort to revitalize Downtown. He said Sifakis is working to make the core a “destination of choice,” transforming it from a place where people feel they have to come for work or business to a place they want to visit.
“The bones of Downtown are so good,” Moll said.
“The tree canopy, the walkable blocks, the historic buildings. The fact that you can do something like we’re doing at Pearl Square one block away from City Hall, I’d love to know where else you can do that in America in a city of over a million people and a metro with close to two million people,” he said.
“For him to recognize that and very early on to start assembling properties is pretty remarkable.”
