South Olive’s longtime director, Skip Jackson, is disqualified after speaking at City Commission meeting.

When Skip Jackson spoke at a West Palm Beach Commission meeting this month, the popular tennis pro hoped to persuade city leaders to let him continue to oversee programs at South Olive Park as he has for more than two decades.
Instead, roughly 14 hours after his plea, he got an email from the city’s procurement director, alerting him that his appearance violated the city’s “no contact” rules and his bid to extend his contract to run the tennis center had been thrown out.
“Skip Jackson Tennis, Inc. is disqualified from participation,” wrote Donna Levengood, the city’s procurement official.
Further, she wrote, the city would no longer consider the bid protest Jackson filed that temporarily blocked the city from handing Orlando-based USTA Florida the contract to run South Olive and the city’s two other tennis centers.
“No protest,” Levengood wrote. “A respondent who was disqualified under Section 66-121 is not eligible to file a protest.”

Does ‘cone of silence’ extend to public meetings?
The sweeping disqualification is the latest bomb that has rocked the city’s tight-knit tennis world.
In picking USTA Florida, city officials not only ousted Jackson from South Olive but also removed Mark Jones from his roughly two-decade job as director of the Howard Park Tennis Center. USTA Florida would also take over the tennis center at Gaines Park, which has been without a pro for more than a decade.
While multimillion-dollar improvements at Gaines Park are ongoing, the tennis courts at South Olive and Howard parks were recently renovated with roughly $5 million in tax dollars.
Attorney Bernard Lebedeker, who filed the bid protest on Jackson’s behalf, said the fight is far from over. By the end of the month, he said he plans to sue the city for violating its own rules by disqualifying Jackson.
The so-called “cone of silence” that prevents bidders from lobbying city officials doesn’t apply to public meetings, Lebedeker said. It is designed to keep decisions from being made in back rooms.
According to city rules, those seeking city contracts are prohibited from contacting “the mayor, any city commissioner” or other city officials about their bids. Contact is defined as “any form of communication or interaction seeking to influence the selection or award of a contract, including instigation of an organized effort of mass communication.”
Lebedeker insisted that Jackson didn’t violate that rule. “Skip Jackson wasn’t addressing the commission as a bidder or a contractor but as a citizen who has been part of this community for decades,” Lebedeker said. “He has real concerns about the process.”

City lost similar challenge over Sunset Lounge
Attorney Malcolm Cunningham, who isn’t involved in the tennis contract but successfully sued the city over the disqualification of a firm that bid to operate the city’s historic Sunset Lounge, agreed.
“This ‘no lobbying’ provision doesn’t apply to a City Commission meeting,” Cunningham said. It’s to stop people from meeting privately with elected officials and department heads.
The situation, he said, is frustrating and baffling.
In a sharply worded 19-page ruling, Circuit Judge Carolyn Bell in 2023 ruled that the city’s Community Redevelopment Agency improperly disqualified Vita Lounge from getting the contract to run the storied club. The agency failed to act in “good faith” when it threw out the bid simply because people sent letters to city officials on Vita’s behalf and one of its principals did a TV interview, Bell ruled.
Cunningham said city officials should have learned from that decision.
“I don’t know why they want to use disqualification so readily when they’re not following their own rules,” he said.

‘I’m not here to argue legal points’
Citing attorney-client privilege, Lebedeker declined to say whether he talked to Jackson about presenting his case to the City Commission.
But, Mayor Keith James, a lawyer, reminded Jackson that he could be treading on shaky legal ground. “You understand you are under a cone of silence, right?” James asked when Jackson approached the podium.
“Absolutely,” Jackson replied as about 20 supporters, including Lebedeker’s wife, looked on.
“I’m not here to argue legal points,” he said. “I’m here as a person who has lived this program for more than two decades. South Olive is one of the most successful programs in the county.”
While Jackson didn’t detail the allegations Lebedeker raised in his 10-page bid protest, the tennis pro referred to them. “Key information was not disclosed and significant scoring irregularities occurred,” Jackson said.
He concluded by urging the commission to allow him to continue to run the tennis program.
“We’re not asking for special treatment, only fair treatment,” he said. “I am respectfully asking the commission to ensure the South Olive contract goes to the operator who has actually demonstrated the experience, transparency and community commitment that this city requires.”
Jennifer Jackson-Strage, the secretary of his company, echoed her husband’s comments as did about 10 tennis players.
Like many of Jackson’s supporters, Sarah Stuebe told the commission about the community Jackson has built at South Olive and how important he is to her and other players.
“But even if you’ve never met Skip or picked up a racket, imagine this: You spend more than 20 years building something, pouring your heart, your time, your energy into it only to be told now it will be handed to somebody else,” Stuebe said. “That’s not partnership. That’s displacement.”

Sexual assault verdict not mentioned
In addition to facing the prospect of having the center yanked away from him, Lebedeker said Jackson had good reason to question the selection process.
The plan by USTA Florida to charge people to use hard courts is the antithesis of Jackson’s philosophy of making tennis open to everyone, he said. It would also make it one of the only cities in Palm Beach County to charge players to play on hard courts.
In its bid, USTA Florida also said it had “no pending lawsuit, and/or past litigation relevant to the subject matter of this solicitation.”
It didn’t mention that its parent organization, USTA, in 2024 was hit with a $9 million verdict after an Orlando jury found that it hadn’t protected tennis player Kylie McKenzie from being sexually assaulted by a coach at its Orlando training facility. The USTA is appealing the decision.
It also didn’t mention that the USTA settled a similar lawsuit filed on behalf of a 9-year-old player in California.
Given the close connection between USTA Florida and its parent organization, both lawsuits should have been divulged, Lebedeker said in the bid protest.
He also said that the scoring seemed to have been manipulated to make sure USTA Florida got the contract. Three of the five city staffers who reviewed the bids gave each of the six hopefuls nearly identical scores — a situation Lebedeker described as “highly unusual.”
Jackson wasn’t the only bidder to object to the award.
Let’s Play Tennis LLC, based in Palm Beach, also filed a bid protest. In the 22-page document, the company claims the staff committee misunderstood its proposal, credited some of its plans to other bidders and made other errors that robbed it of high scores it deserved.
Levengood rejected the firm’s claims on Dec. 10. “The solicitation process was fair and impartial and conducted in accordance with the City’s Procurement code and the terms of the solicitation,” she wrote. “No procedural or legal errors occurred. The protest is denied.”
Let’s Play has appealed the decision to the City Commission. Lebedeker said he was told that it will be heard in January. Neither city officials nor those from Let’s Play Tennis responded to requests for comment.
The situation is unfortunate, Lebedeker said. City officials should be embracing local residents, like Jackson and Jones, who were raised in West Palm Beach and spent decades building successful programs.
“Twenty years is a long time. Why would you take that and throw it in the trash for the next new shiny object?” he asked. “Why does this city pick the rich guy over the not-so-rich guys they’re supposed to be supporting?”
Watch the City Commission meeting here. (Jackson speaks at 2:25:40.)
