People to Watch: Main Plaza developer strives to reflect community vision

David Chessler sees the redevelopment of Main Plaza as more than just an opportunity to capitalize on an underused site — it’s a chance to shape the future of the city he’s made his home.

Chessler teamed with two other Sarasota entrepreneurs, Eric Baird and Jesse Biter, to purchase the 8.6-acre downtown mall for $18.1 million in November. The three friends learned of the opportunity through Biter, eventually closing on a deal for less than half of its 2005 sale price of $40 million.

It’s a different type of endeavor than what Chessler usually oversees as chief investment officer for the Great White Shark Opportunity Fund, a partnership with PGA golfer Greg Norman focused on smaller businesses.

Still, he believed each member of the trio could play a valuable role in revitalizing an aging office and retail hub. Together, they would make sure Main Plaza was redeveloped right.

“We all have kids that are growing up here in Sarasota, and we want to make sure the development we have is something our kids and downtown can be proud of,” Chessler said. “That’s a big piece of why we want the property — we want this to benefit the community.”

There’s been no shortage of public input on what should happen to the property since the sale was announced, Chessler said. The ownership group has encouraged that input, soliciting suggestions online and publicly inviting architects to submit plans for the first phase of redevelopment.

The initial work will focus on refurbishing the plaza’s existing retail footprint. Chessler wants the mall to present a more distinguishing face to visitors — right now, he said, you can walk down the 1900 block of Main Street without realizing what’s actually inside the commercial complex.

The ownership group will meet with architects next week to consider the finer details of a redesign. Already, Chessler has heard some recurring notes. People want to keep a movie theater, although Chessler said current lessee Regal Cinemas has expressed an interest in reducing its current 20-theater footprint to concentrate on a more upscale product. People want local stores and restaurants. They want a unique, open space in which they can hang out.

The group has announced a preliminary three-phase redevelopment plan: First, the retail improvements, then, the theater rehabilitation. The third phase is more ambitious and fluid, because the owners are considering constructing a new, large building on the north end of the site.

That could be a hotel, multifamily housing project, conference center — or something else. Chessler said the group won’t be rushing to market on that phase of the project as it continues to gauge the right fit for the location and the city.

“There’s no need to pop up another hotel just because we want to pop up another hotel,” Chessler said. “We want to build a first rate establishment, and we want to cater to the needs of Sarasota.”

That sort of deliberate, considered mindset is a guiding force for the partnership overseeing this redevelopment, Chessler said. The group does hope to take action soon — residents should start noticing changes in the next few months if all goes according to plan — but Chessler also wants to make sure any changes have a lasting impact.

“We’re not in this to generate an instant cashflow,” he said. “We look at the project over the long term, take our time and make sure we have a well- thought-out plan.”