It was a tale of two starkly different opening statements during Samir Cabrera’s first day in court.
In a dry, halting and complex explanation of the fraud and money laundering charges against the 31-year-old Fort Myers real estate agent, federal prosecutors described a man who broke the trust of investors when he flipped two south Fort Myers properties without disclosing serious markups in the prices and then pocketing the $2.8 million difference.
“As managing member, Mr. Cabrera had a fiduciary responsibility to the investors,” Assistant United States Attorney Robert Barclift told jurors. “That meant he had a duty to look out for their best interests.”
Cabrera’s defense countered with the narrative of a young, driven entrepreneur burned by the steady hands he hired to guide him through a high octane housing market. His lawyers simply failed to disclose the deals, defense attorney John Mills said.
“Now, with the FBI sniffing around, no one wants to admit they made a mistake, and everyone wants to point a finger at Mr. Cabrera,” he told jurors.
It is up to a jury of 12, selected earlier in the day, to decide which account is most plausible and, perhaps, easiest to understand.
Cabrera’s day in court follows his August indictment for 12 felony counts of fraud and money laundering. He could receive 20 years in prison for each of the seven fraud convictions, and 10 years maximum for every money laundering conviction.
Both parties agree on many of the facts: Cabrera owned a company that purchased two commercial lots on Fiddlesticks Boulevard, off Daniels Parkway, in 2006. On the same day of each purchase, he resold the lots, at a substantial mark-up, to investor-funded companies he managed. He and his associates shared the profit, known as “kicker fees.” Cabrera’s involvement in the first company was never disclosed to investors.
The question of whether that failure was intentional is central to the trial.
In his opening statement, Barclift, the prosecutor, dissected the numbers for each deal. He leaned on a podium before the jury and looked down into his notes, often pausing as he moved between points or between the charts he placed on an easel. He told jurors how much money had been invested in both deals, how much was promised in return and the amounts Cabrera and multiple associates split between themselves.
“However, in the end, you’ll see that the lion’s share of money stolen, in the form of these kicker fees, found its way to Mr. Cabrera himself,” he said.
Mills began by telling the story of Cabrera’s ascent from Bonita Springs nightclub manager to real estate agent to big time deal broker. With a hunger to take advantage of a heating housing market, he found himself under the tutelage of Frank D’Alessandro, an area real estate magnate who died last year.
Cabrera and a group of like-minded associates pooled their money to buy properties and sell them for profit. The kicker fees, Mills said, were like a commission for each deal, a perfectly legal way of rewarding the associates’ risk.
Needing legal help to close the deals, Cabrera hired two lawyers to handle logistics. Both failed, Mills said.
“We all know there was no disclosure,” Mills said after court was adjourned. “Our defense is why there was no disclosure.”
The complexities of the case were apparent in jury selection, which lasted most of the day. Cabrera’s marriage to former NBC-2 anchor Jessica Stilwell was the subject of several questions for each round.
When Assistant United States Attorney Jeffrey F. Michelland asked one woman if she watched NBC-2 and knew Stilwell, the woman responded, “Yes, I watched all the time. She was one of my favorites.”
The juror was dismissed soon after.
Stilwell sat in the back of the courtroom, alongside Cabrera’s two younger brothers and his father, as well as several friends.
Cabrera’s father-in-law, Lee County Manager Don Stilwell, was also a subject of several questions. Stilwell received money from Cabrera and was the subject of a county investigation into whether he breached county ethics by investing in the deals. He was found innocent of the allegations.
Of the 12 regular jurors chosen, eight were women. Juror backgrounds ranged from registered nurses to school teachers, and they lived as far north as Port Charlotte and as far south as Naples.
The trial, which is expected to last two weeks, will continue today.

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