Jacksonville City Council President Nick Howland climbed aboard a Gulfstream G280 owned by Tampa Bay Rays owner Patrick Zalupski on August 30, flying from Jacksonville International Airport to St. Petersburg-Clearwater International Airport for a Rays game at Tropicana Field. The flight lasted about 40 minutes each way, with the jet returning to Jacksonville that same evening. Howland says the trip was tied to a fundraiser for his political committee, Florida Freedom PAC.
The excursion was first reported by The Florida Trib, and later covered by Creative Loafing Tampa. Zalupski's corporate jet was registered to a company connected to his homebuilding firm, Dream Finders Homes, and the plane carried Howland and others to the game. Howland said the fundraiser will be disclosed in the committee's finance reports as required under state law, though he declined to share further specifics about the event.
What makes the flight legally permissible, despite its optics, is a quirk in Florida's campaign finance rules: political committees can pay for travel connected to campaign activity, and private-plane seats can be valued at the price of an economy-class commercial airline ticket rather than what it actually costs to operate a private jet. Florida political committees can also receive donations in unlimited amounts, meaning the financial guardrails that might otherwise raise flags simply do not apply the same way to this kind of trip.
A Billionaire With Business Before City Hall
Zalupski is founder and chief executive officer of Jacksonville-based Dream Finders Homes, and led the investor group that closed on the $1.7 billion purchase of the Tampa Bay Rays from previous owner Stuart Sternberg in September 2025, a deal unanimously approved by MLB owners, according to MLB.com. Sternberg had owned the team since 2004 after purchasing it for roughly $200 million. Forbes estimated Zalupski's net worth at $1.4 billion in 2025, per WUSF.
Dream Finders Homes has employed six lobbyists registered with firms working before Jacksonville city government, and Zalupski himself has two lobbyists registered with the city. Under Florida Statute § 112.3148, municipal elected officials like Howland are prohibited from accepting gifts worth more than $100 from registered lobbyists or their employers — a rule the campaign travel accounting method effectively sidesteps for flights classified as political committee expenses.
The UF Campus Connection
Zalupski's ties to Jacksonville City Hall extend beyond his homebuilding business. He is an appointee to the University of Florida Board of Trustees, having been placed there by Governor Ron DeSantis, and he has advocated for Jacksonville's financial investment in a planned UF graduate campus set for downtown. The Jacksonville City Council committed more than 20 acres of public land in LaVilla and $100 million in direct funding toward the $345 million project, according to UF News, with the future campus expected to focus on graduate programs in medicine, engineering, and business.
Zalupski's political reach in Jacksonville crosses party lines. In May, he served on the bipartisan fundraising host committee for Democratic Mayor Donna Deegan's 2027 re-election campaign, a role that followed $50,000 in corporate contributions from Dream Finders Homes earlier in the election cycle, as reported by Florida Politics.
Echoes of a Familiar Jacksonville Pattern
Former Jacksonville Mayor Lenny Curry, who now lobbies for Dream Finders Homes, was also in St. Petersburg for the same game weekend. Curry routinely funded travel through his own political action committee while in office, a practice that has made PAC-financed travel a long-running point of controversy in Jacksonville politics. Jordan Elsbury, Curry's former chief of staff, is also named in reporting tied to the trip.
Former Jacksonville City Council member Matt Schellenberg offered a blunt assessment of the arrangement. He said he would have simply driven nearly four hours instead of accepting a seat on a private plane, and argued that funneling the trip through a political committee actually looked worse than if Howland had just paid for it himself. “Elected officials must be as transparent as possible,” Schellenberg said, adding that the trip looked very suspicious to him because it was not done openly.
Howland formed Florida Freedom PAC in August 2021 during his initial council campaign and had built the committee up to roughly $340,000 by July, according to Florida Politics. He first won his At-Large Group 3 council seat in a February 2022 special election and now serves as council president.
A Franchise, and a Homebuilder, Still Growing
Zalupski's Rays are separately pursuing a new ballpark in Tampa for after the 2028 season, following $57 million in Hurricane Milton repairs to Tropicana Field in late 2024 and funding disputes with Pinellas County commissioners — context Hoodline has tracked in earlier stadium talks. The team's current Tropicana Field lease runs through the 2028 MLB season, and Zalupski has secured an agreement to build the new stadium in Tampa.
Back in Jacksonville, Dream Finders continues to seek land-use approvals from the same city government Howland helps lead, including a March environmental permit filing to redevelop 28 acres of the Prominence Office Park in Baymeadows into a 204-unit townhome community, a project Hoodline previously covered after the firm purchased the 68-acre campus in 2024 for $22 million. Creative Loafing Tampa republished its article on the flight under a Creative Commons Attribution-NoDerivatives 4.0 International license.
