An hour before the town council’s regular meeting and before passing the resolution, council members met with Shutts & Bowen attorneys in a “shade meeting,” a closed-door session in which, according to Florida Statute 286.011(8), officials are permitted to meet privately with their attorneys, provided the subject matter is restricted to "settlement negotiations or strategy sessions related to litigation expenditures."

The agenda for Windermere's shade meeting indicated it would cover “strategy related to litigation on the pending appeal of the case.”

Shade meetings are conducted in private, but the statute says the meetings must open and close within a public meeting and include a court reporter.

Town officials, who have never explained why they want the properties or what would be done with them if the town owned them, have long maintained that the owners of the boathouses should have turned the structures over to Windermere under a 1986 lease agreement between the town and owners at the time. The 10 former and current residents, who are the defendants in the town’s lawsuit, insist the boathouses are their private property. In October, a judge ruled in favor of the residents and denied the town's motion to evict them from the structures and find them in breach of the contract.

The lawsuit has drawn increasing attention from local residents opposed to the town’s continued pursuit of litigation. The first time council members held a shade meeting, around Halloween, protesters gathered outside Town Hall, holding signs that called for an end to “the lawsuit that refuses to die.” 

More recently, at Tuesday’s council meeting, Windermere Historic Preservation Board Chair Joan Foglia told council members that the town had spent “hundreds of thousands of dollars in legal fees,” for a lawsuit the town ultimately lost.

“Many long-standing relationships in this town have been destroyed and severed, dividing our community over this issue,” Foglia said. She said the funds spent on the boathouses should have been spent restoring Town Hall. 

“The current estimate that I have for renovations for the Town Hall is between $1.7 and $2 million at this time,” she said. “I just don't want to see any more money spent without resolving the issue in the best interest of all the residents in the town.”

During the discussion over a budget amendment item on Tuesday’s agenda, Town Manager Robert Smith admitted the town’s administrative budget has faced “legal fees that were well outside” of what had originally been budgeted. 

Initially, $225,000 was budgeted for legal fees for Fiscal Year 2024-2025; the actual costs for that year totaled $302,018 — a more than 34-percent increase. As of October, the town had spent upwards of $637,000 in taxpayer funds to litigate the boathouse lawsuit — that number has only grown since the town opted to appeal the Ninth Circuit Court's decision.

Tuesday, ahead of the vote on the resolution, Foglia urged council members to consider what the “end goal” was in pursuing the boathouses.

“Do we, as a town, intend to own those boathouses?” she asked. “I don't know what the end goal is here. What does the town need to do to settle the unanswered question of who owns land beneath the boathouses … Will this appeal answer that question?”

The council provided no answer.