Jacksonville Council President Takes Billionaire’s Private Jet to Rays Game

Flight Details and Political Committee Funding

According to publicly available flight data cited by the Florida Trib, the corporate Gulfstream G280 jet owned by a company connected to Dream Finders Homes departed Jacksonville International Airport on a Sunday morning. The 40-minute flight landed at St. Petersburg Clearwater International Airport, carrying Howland and other passengers to watch the Rays play. The aircraft returned to Jacksonville later that evening.

When questioned by the Florida Trib, Howland stated that the trip was connected to his political committee, the Florida Freedom PAC, and that he attended the game to help raise funds. “It will all be disclosed in the committee’s finance reports as required by Florida law,” Howland said, while declining to share specific details about the fundraiser. Zalupski, who purchased the St. Petersburg-based baseball team last year and recently secured an agreement to build a new stadium in Tampa, did not return multiple requests for comment from the publication.

Campaign Finance Rules and Lobbyist Ties

Under Florida law, elected officials are barred from accepting gifts valued at more than $100 from lobbyists or their employers. However, state campaign finance regulations permit officials to utilize political committees—which can accept unlimited donations—to finance travel expenses if the trip is tied to campaign activity, such as a fundraiser. Furthermore, officials can price private plane seats at equivalent commercial economy-rate airfares, significantly discounting travel costs.

Zalupski and his company, Dream Finders Homes, employ multiple lobbyists registered with Jacksonville City Hall, including former Mayor Lenny Curry and Curry’s former chief of staff, Jordan Elsbury, both of whom were also present in St. Petersburg according to social media posts. Zalupski also previously advocated for City Hall’s financial investment in a planned University of Florida graduate campus in downtown, a project that secured millions in public land and $100 million in direct support from the city.

Public Scrutiny and Past Travel Controversies

Travel financing via political committees has a documented history in Jacksonville politics. Former Mayor Curry frequently financed his travel using a standing political action committee partially funded by the owner of the Jacksonville Jaguars. While direct gifts to elected officials require strict disclosure, transfers or payments made directly to an associated political committee avoid direct gift disclosure rules, with reimbursements appearing only in committee expense reports.

Former Jacksonville City Council Member Matt Schellenberg criticized the arrangement, telling the Florida Trib that he would have driven the four-hour distance rather than take a private flight. “He’s supposed to be a leader,” Schellenberg said regarding Howland. “We’re in a political environment where everything is suspicious, and this, in my opinion, looks very suspicious that he didn’t do it in the open.”