Developer to take on Texas-sized new role

John Simon, lead developer behind a highly anticipated project in downtown Sarasota stalled by the recession, is about to add a new wrinkle in his pursuit: a lot more time on an airplane.

The CEO of Pineapple Square Properties in Sarasota, Simon recently accepted a new position, to run strategic planning for the Howard Hughes Corp., a Dallas-based publicly traded real-estate firm. The 850-employee company owns and manages 34 sites in 18 states, from New York to Hawaii.

Although that job promises to capture a lot of Simon’s time — and frequent flier miles — he isn’t going to give up on Pineapple Square. That project, which covers an area around Lemon and Pineapple avenues and Main Street, was originally planned as a $200 million mix of condos, retail and office space. Some of the retail has already opened, such as Brooks Brothers on Main Street.

“The rumors in town of my having left town are inaccurate,” Simon said Tuesday. “I’m committed to Sarasota. I’m committed to making Pineapple Square work.”

To make the project work, the first step was to reshape what it will be. Simon accomplished that late last year, when he and Sarasota city officials agreed to a revised development plan. The original agreement called for 157 condos and about 85,000 square feet of retail space. But the recession made condo sales unworkable, Simon said.

The new plan, however, allows Simon to build something other than condos, possibly a hotel, on property the development firm owns at Lemon and Pineapple avenues. Simon, one of the Sarasota Observer’s seven people to watch in 2011, has been in several discussions with a number of three-star hotel operators. He declines to name any of the potential partners.

Simon said other possibilities for the site include Class A office space and apartments.

Still, to make any of those options work, Simon, who said he has invested a substantial amount of his own money into Pineapple Square, faces a hurdle common to many other developments: lack of financing.

“The fundamental issue,” said Simon, “is when lenders will begin to lend for new developments.”

Simon said he’s hopeful that issue will improve by the end of 2012. In the meantime, he will maintain a home and an office in the Sarasota-Bradenton region and Dallas. For Pineapple Square, he said his location isn’t a high priority because the work involves meetings with nationally based lenders.

Simon will resign from two downtown Sarasota-focused board positions to make more time for his Howard Hughes Corp. responsibilities. But he plans to remain active on the Sarasota Ballet Board of Directors, for which he’s the Governance Committee chairman.

In a January interview, Simon emphasized his belief in downtown Sarasota.

“How lucky you are to have a hardware store downtown that is not chased out by Home Depot or Wal-Mart,” he said in January. “There are no less than four barbershops. This is a community that uses its downtown. It’s unlike other downtowns that have burned out areas.”