A long-running battle over downtown Sarasota’s skyline is likely headed to circuit court after city commissioners this week narrowly rejected for the third time a proposed high-rise that would become the city’s tallest building.

The proposed condo tower, formerly known as The Obsidian, has drawn widespread opposition over its height and design. Although it met the city’s 18-story limit, developers had included extra space between floors, making the proposal dramatically taller than other nearby buildings.

For three years, angry residents packed City Commission meetings, organized rallies and hired their own experts and attorneys to fight the project. About 45 opponents filled the commission chambers again Monday, donning custom red T-shirts reading “Say NO To the Skyscraper On Palm Ave.”

The proposed tower would have stood 320 feet tall at 1260 North Palm Avenue, becoming the new centerpiece of Sarasota’s skyline, despite containing just 14 condo units. 

After commissioners rejected the project twice, the developer filed a petition under a Florida law designed to resolve land-use disputes without litigation. The special magistrate over that case has largely sided with the developer, determining that the city’s prior action was unreasonable and unfairly burdened the property owner. The magistrate recommended the commissioners reverse their earlier votes and approve the project.

But the commission rejected the project in a 3-2 vote.

“This is a matter of compatibility — or the lack of it,” Commissioner Kathy Kelley Ohlrich said. “The buildings, to me, are totally out of scale.”

Obsidian’s opponents have argued the building was out of character, benefiting only the wealthy buyers who would live there at the expense of the entire city.

Commissioner Liz Alpert, who voted to move the project forward, was concerned about the possibility of a costly legal battle.

“My concern is that by rejecting this, we’re opening up the city to multiple millions of dollars in damages,” Alpert said. “I’m worried about taking on that financial risk.”

Plans for the Obsidian first arrived at City Hall in late 2022, drawing immediate opposition from residents in the nearby Bay Plaza, a 14-story condo built in the 1980s that borders the quarter-acre lot eyed for the new development.

Bay Plaza residents accused the developer of exploiting a loophole in the city’s zoning code to maximize height and waterfront views. They argue the tower would cast shadows, create a wind tunnel and fundamentally alter the neighborhood.

Residents have told reporters that one corner of the project would come within arm’s reach of their building. They’ve argued the project should be rejected based on compatibility concerns.

On Monday, lawyers representing the developer and its neighbors went head-to-head in what amounted to a heavyweight rumble.

“This is one of those ‘emperor has no clothes’ arguments,” said Morgan Bentley, a prominent Sarasota trial attorney hired by opponents of the Obsidian.

“This is really low-hanging fruit for you guys,” Bentley told the commission, urging them to reject the special magistrate’s recommendation.

Robert Lincoln, the attorney for the developer, said there will be legal action if the city again turned down the development.

“You are free to reject it,” Lincoln said. “I do not think it would be a good idea.”

Sarasota and the Obsidian is a long-running drama at City Hall

The project’s developer, Matt Kihnke, has spent more than three years trying to win approval for the tower, revisiting plans and marshaling a team of engineers, planners and attorneys to address concerns about its height and impact on surrounding buildings and pedestrians.

But those efforts failed to sway opponents, who packed the City Commission chambers in May 2025 wearing red shirts and urged elected officials to block the project over concerns about compatibility with surrounding buildings. 

The project has been tied up before a special magistrate ever since — and will likely now head to a circuit court judge.

Martin Hyde, an independent candidate for state senate, and John Harshman, a candidate for Sarasota City Commission, both spoke out against the project at Monday’s meeting. The only public comment in favor of the project was Jonathan Abrams, a luxury real estate agent with Michael Saunders and Co.

When it came time for the board to vote, Commissioners Jen Ahearn-Koch and Kathy Kelley Ohlrich signaled their opposition to the development. 

Commissioners Liz Alpert and Kyle Battie followed by saying although they had apprehensions about the project, and its effect on Palm Avenue, they were also concerned what a losing effort in court could do to the city.

The swing vote came down to Mayor Debbie Trice, who presided over the dais at her last meeting before a new commissioner would be sworn in to replace her on Friday. Trice is not seeking re-election.

“My apologies to the Bay Plaza people: You are a small subset of the population,” she began, seeming to indicate that in her last major act as a commissioner, she was prepared to allow the Obsidian through.

Trice then went on to state her apprehensions to the project, calling that section of downtown “a bit of a jewel box.” In the end, Trice voted against the development in a 3-2 vote, to a surprised adulation from the red shirts.