Once upon a time, when the markets were hot and money was moving, Frank D’Alessandro was king of Southwest Florida real estate.
Then the bubble burst, and the empire collapsed. Projects failed and investors lost large sums of money. Lawsuits popped up. D’Alessandro died in 2007, after drowning during a kayaking trip.
The rise and fall of his fortunes were visited in a Fort Myers federal courtroom on Tuesday, when one of his real estate agents testified against his colleague, a man who was supposed to be D’Alessandro’s protege: Samir Cabrera, a 31-year-old real estate agent on trial for 12 counts of fraud and money laundering.
Cabrera was to blame for many of the failed projects, said Don Turner Jr., who worked with Cabrera at real estate brokerage D’Alessandro & Woodyard.
“Too many things were done at one time,” he said. “There were too many projects at one time.”
Turner also testified that Don Stilwell, the Lee County manager who survived an ethics investigation into his relationship with Cabrera, his son-in-law, met with Turner and D’Alessandro to discuss Cabrera’s troubled projects in 2006.
Two of those projects, on Fiddlesticks Boulevard in south Fort Myers, are the focus of Cabrera’s trial. Cabrera bought the two lots and then resold — or “flipped” — them to investors at a higher price without telling them he was the seller.
Prosecutors say he meant to hide the flip; Cabrera and his defense attorney say two lawyers with his firm made a big mistake.
On Tuesday, Turner described a hot development market in 2004 that brought the best real estate agents to D’Alessandro & Woodyard, where “phones were ringing all day long.” Cabrera was one of the biggest stars, he said, and one of the closest to D’Alessandro.
“He was confident. He carried himself well. He was well dressed,” recalled Turner.
Cabrera was also driven. With partners from the firm, he formed several companies to buy and move properties for development. In early 2006, he gathered fellow agents to make a fund-raising push for the Fiddlesticks properties, off Daniels Parkway. The flips were planned from the beginning, Turner said.
“They told us they were going to sell to another entity and give us our fees out of that,” he said.
D’Alessandro would finance the projects with special high-interest loans to be repaid in a year. Given the fast pace of the market, a year was ample time to pay it back, the thinking went.
Instead, construction loans began drying up in 2006, and ground was never broken on either site. Investors were left in the lurch. Everyone lost their money.
James E. Andersen, a property manager from Port St. Lucie, testified about losing $50,000 in one of the Fiddlesticks lots. His face reddened as he described how investment documents never mentioned the lot had been flipped, and that he was on the wrong end of it.
“Had you known that, would that have been material to your decision to invest?” asked Assistant United States Attorney Jeffrey Michelland.
“Significantly so,” Andersen eagerly replied.
Prosecutors worked to connect the flips to the failures of both projects. Michelland asked Turner if the $900,000 profit from one of the flips could have been used for loan payments, instead of going toward Cabrera and his associates, as was the case.
It could have, Turner replied.
Instead, project accounts withered. Turner said D’Alessandro knew little about what was happening, despite financing the projects. The two met at Stilwell’s house, and with the county manager present, pored through the account books.
D’Alessandro called another meeting soon after, this time with Cabrera present.
“At that meeting, Frank told us all that, pardon my language, we were all pretty much screwed,” Turner said.
Cabrera said little during the meeting, Turner recalled.
Later, he said, Cabrera began pulling his own money out of the failing ventures. When Turner said investors should get their money first, Cabrera scolded him, he said.
“He said it was just business, and that’s part of the real estate (business). Sometimes things go bad, and you can’t get emotionally involved,” Turner recalled.
Michelland then asked, “How many of his deals went bad?”
“His deals?” Turner asked.
“Yeah,” Michelland said.
“All of them.”
Prosecutors introduced eight witnesses Tuesday, including D’Alessandro’s former business partner, Tom Woodyard. Combined, the witnesses established a timeline of Cabrera’s investments, his involvement with D’Alessandro and D’Alessandro’s high-interest loan business.
Cabrera’s attorney, John Mills, cross-examined some of the witnesses but left much of the day to the government. In his few crosses, Mills emphasized that property flips were only illegal if not disclosed.
Cabrera’s defense centers around two of his former attorneys, who he said should have overseen the disclosures.
Cabrera followed Tuesday’s testimony closely, leaning forward in his chair and looking from attorney to witness during testimony.
He grimaced when Roseanne Gauthier, a co-partner of D’Alessandro’s loan business, said he was a poor loan negotiator.
Before testimony began, a juror was excused from the trial after she complained of back spasms. She was the second juror dismissed since the trial began. Another juror, a man, was released when he said he could not miss work for the two to three weeks of the trial.
The court now has only three alternates.
Witness testimony will continue today.

Steven Beardsley is a staff writer for the Naples Daily News.