Ponzi Playboy Sean Healy Blew Through the Money He Swindled

Sean Healy sat fidgeting in a low, black-leather chair, stuck in a sixth-floor law-firm conference room overlooking SE Second Street in downtown Fort Lauderdale. It was April 7, 2009, and he was being asked a series of questions usually reserved for Las Vegas barmaids.

"Do you know Dennis Rodman?"

"Sure," he replied.

"How many times have you met Dennis Rodman?"

"A dozen or so."

And the inevitable, given the circumstances of the lawsuit: "Has Dennis Rodman ever given monies to you or your wife?"

"Ever given monies to us? No."

Healy is more often red in the face than not, perhaps six-foot-three, with close-cropped brown hair and a penchant for Ed Hardy T-shirts. The 39-year-old had put on weight from the stress of the past few months, and his sleep apnea had been flaring up, leaving the self-proclaimed day trader exhausted when he woke up at 4 a.m. to greet the market.

It was 1:30 in the afternoon, and Healy had to get out of there, and fast. He shifted from side to side in his seat, sending the chair's silver wheels rolling across the wood-paneled floor. He stood. He paced, his eyes flitting down to his oversized watch.

Across from Healy sat Paul Turner, the attorney who had filed the multimillion-dollar lawsuit against him. The suit claimed Healy had duped Pennsylvania chiropractor Alfred Madeira out of at least $11 million from May 2008 to March 2009. It was part of a Ponzi scheme Healy ran that would steal up to $16 million from about 40 investors.

The afternoon slid on. Turner showed Healy handwritten documents that were faxed to Madeira as proof that the chiropractor's money was being invested well. Sean shook his head. He hadn't faxed those, and if he had written the documents — and he wasn't admitting he had — then the signature wasn't his. And the number at the top looked crooked.

Hours ticked by. Sean angled forward in his chair, cheeks red. He'd mumble and interrupt Turner's questions.

Healy requested a recess. He said he was having heart problems. When they reconvened, his attorney, Richard Bales, announced that Healy had to stop. "I looked at the guy, and he looks bad," Bales explained.

"I think he looks bad because of the questions that are being asked, not as a result of a medical issue," said another attorney, Matthew Lipman.

As it turns out, they were both wrong. Bank and phone records would show that Healy did have to get out of there — but not because of Paul Turner's increasingly dangerous questions and not because of a heart condition.

If he hadn't left then, Healy would have missed tip-off for the Miami Heat game.

Healy raced off to his private box to see the Heat lose 87–93 to the New Orleans Hornets. That night, he texted one of the victims — whom he was trying to pay off — "Hey, I'm at the game, want to come by?" He finished the night by plunking down $1,200 at Passion Night Club at the Hard Rock Casino in Davie.

Unlike most Ponzi perps, Healy never invested a single dollar of Madeira's money. Instead, he and his wife, Shalese, blew it quickly on a fleet of fast cars, strip clubs, private jets, Bahamas getaways, and a Weston mansion. Healy's spending spree left his wife, four young kids, a half-dozen legal minds, and a courtroom of victims to wonder:

What the hell was he thinking?

Things had not always been good for Sean Healy. Growing up in suburban New York, he was only about 12 when his father passed away. His mom went back to school for interior design. Sean liked playing hockey, but he went down hard one day and came back up needing a metal plate in his ankle.

His mother, Karen, thought Healy needed a structured environment with male role models, so she sent him to the La Salle Military Academy, a now-defunct all-boys Catholic school in Oakdale, New York. Healy's quick, sarcastic sense of humor roped in friends. He had a way about him that made people want to be near him, all hugs and handshakes and "how are you?"s.

Healy had a difficult time adjusting at La Salle, where most of his classmates were wealthy. He'd comment on how his friends' fathers were CEOs or Mob bosses or both. But he ended up doing well, graduating with honors. He went on to Northeastern University but after three years transferred to the University of Rhode Island, where he studied business administration and graduated in 1992. The next year, he married and had a daughter. Two years later, he and Christine Healy had a son.

Healy took a job in Long Island as a junior broker but quit to start his own firm with friends. His career took a criminal turn by 1997, when Healy was working at his third boiler-room operation in New York, according to Turner. At Guru Investments, he cold-called wealthy investors with promises of high returns that never materialized.

KEEP NEW TIMES BROWARD-PALM BEACH FREE... Since we started New Times Broward-Palm Beach, it has been defined as the free, independent voice of South Florida, and we'd like to keep it that way. With local media under siege, it's more important than ever for us to rally support behind funding our local journalism. You can help by participating in our "I Support" program, allowing us to keep offering readers access to our incisive coverage of local news, food and culture with no paywalls.
Lisa Gartner
Contact: Lisa Gartner