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.

In late 2008, Healy got a lead with Madeira's information, and Healy talked him into purchasing stock in a music company, then flipping it. Madeira walked away with about $50,000 in profit, and Healy told him there was more to come. Madeira said he was interested, but first, they needed to meet.

A soft-spoken man, Madeira, 54, studied chemistry at a private Christian college before setting up his practice in 1984 in Chambersburg, Pennsylvania. He was a conservative, and he liked to pray on the phone with his friends if they felt troubled.

He had lunch with Healy on Long Island, where he saw Healy's office and the Mercedes he drove. "He was very energetic and outgoing," Madeira says. "He made you feel good."

Healy began purchasing equities for Madeira through Guru Investments, but after that initial win, a satellite company that was going public fell flat, and all the money disappeared.

Healy couldn't apologize enough to Madeira. "If you don't make money on this one, I'll give you shares of another one," he'd say as they planned their next investment.

In all odds, there were never any trades in New York. "It sounds very convenient that on paper, [Madeira's] first trade hit, but at the very end of the day, he broke even," Turner says.

But Healy and Madeira were bonding, and Healy invited his investor to a Good Samaritan Hospital golf fundraiser. That night, he stayed over at Healy's house, met his wife and kids. Other times, Healy would come to Chambersburg, and Madeira would try to pay for Healy's hotel — but Healy would sneak down to the front desk and pay his own way.

By 2000, Healy was confiding to Madeira about his marital difficulties. Things weren't going so hot with Christine, and Healy wanted to start over. "I told him to work things out and see a counselor," Madeira recalls.

But after the dot-com bust, Healy said his investments weren't worth much. He was thinking of heading to Florida. At the end of the year, Healy and his family packed up and moved to Hollywood, where he became president of Dark Dog, an energy-drink company. And he and his dear friend Madeira fell out of touch.

Some believe it began with Shalese Presnell.

They met at the Streets of Miami, a temporary racetrack where two Dark Dog-sponsored cars were whizzing by. Shalese was wearing a bikini.

Shalese, 37, is the kind of gorgeous that stops traffic. Loose waves of long dark hair tent her big eyes, tan skin, and perpetually pouting lips. She's five-foot-six but comes across much taller. Her breasts don't deign to fall toward her torso.

An interior design student and swimsuit model who'd posed her way through Hawaiian Tropics calendars, Shalese met Healy while passing out cans of Dark Dog as part of the racing promotion. She asked Healy about openings in the company, and two days later, she had a job in marketing.

"There was no immediate attraction to Sean," Shalese says. But they could talk about anything. She liked how smart he was, how successful he seemed. They became best friends, "and the friendship turned into, we couldn't not see each other."

But Healy was married, and Shalese was living with a longtime boyfriend. "There was even a point where I almost didn't want to go to work, because I knew that there was this chemistry developing between us," Shalese says. "Sean was very — still is — very much in love with me."

Healy divorced his wife, and according to the December 16 settlement agreement, he would pay $3,000 a month in child support and alimony. In the court papers, he declared an annual income of $75,000.

Within a couple of months, Healy and Shalese married. "He always made me feel like a princess," she says. He bought her little things, jewelry. A recent photo of the couple shows Shalese leaning into Healy, his right hand on her lower back and his left hand holding a flask. Shalese grins through pink lipstick; Healy stares ahead, lips slightly parted, almost a smile.

Healy sent a wedding invitation to Madeira, but the old friend couldn't make it. His father was fatally ill with cancer.

When Dark Dog went under in 2004, Healy claimed he lost half a million dollars. But he still had a limo, and he told his bride that their cash came from investment companies he had owned and sold off in New York. Now, he told Shalese, he had a new idea: day trading.

Healy's Ponzi scheme began with friends and family whom he persuaded to invest in his day trading. Some of his early victims were the parents of kids on his son's hockey team, which Healy coached. Healy liked to have a few families over for football on Sunday or throw big birthday parties in the backyard for his kids.

Healy wanted to be the guy to pick up the check at the end of the night. He wouldn't make a big thing out of it. He and Shalese would meet friends at restaurants and clubs, and Healy would slip to the back, pay the bill, and leave. "Nobody would even know until we left," Shalese said. "I think he just wanted to be the one who did it."

Friends would call asking for loans. They were getting married or starting a new business venture or paying off the new house. If Healy could just give them $10,000 for this, $30,000 for that. "He couldn't say no to people, you know?" Shalese recalls.

As he was being generous with his friends, he was also losing his investors' money. He told Shalese he had lost it all in day trades.

"Please," Shalese asked him, "never get family, friends, anything ever involved again."

"I swear to you," Healy said, "there's nobody else getting involved." He promised he would work with only one investor, his old friend Madeira.

Healy called Madeira in April 2008. "I'm a new man," Healy said. He'd remarried a beautiful woman, with whom he'd had a son and was about to have a daughter. And he was back on his feet financially: He'd already made a million or so, and he was ready to reinvest.

Healy told Madeira that he was bored trading by himself. "Let's say you make maybe $50,000 or $100,000," Healy said. "It's hard to celebrate by yourself." If he celebrated in front of his wife, he told Madeira, then she'd see how much money he made and spend it all.

While Madeira thought about it, the men chatted about their children: how much hockey Healy's son was playing, how tall Madeira's son was getting, how Shalese might need a C-section.

That May, Madeira began wiring Healy money for shares of stock in Ruth's Chris Steakhouse, MySync, and Humana Gold. The wires always went to a Bank of America account in Shalese Healy's name. If it was under his wife's name, Healy explained, his ex-wife couldn't factor his gains into alimony or child support.

He told Madeira he would match each investment dollar for dollar, then wire the money to a New York trader named Matt, who would put the deals through. In June, Madeira learned from Healy — always over the phone — that various oil commodities contracts had netted him $1.6 million. In July, the oil netted another $1.2 million.

Madeira could call whenever, sometimes at 4:30 in the morning, and Healy would be wide awake. Madeira would hear another phone ringing, Healy picking it up. Madeira listened as Healy told the caller, "Uh-huh, uh-huh. Let's make the trade."

In August 2, 2008, Madeira was out in his pool, swimming with his wife and two kids, when a storm abruptly approached.

He hurried his family inside while chatting on his cell phone with Healy. They were talking about how great the trades were going when Madeira heard a loud boom. There was a flash of light. Lightning had struck Madeira's chimney. The call dropped. Bricks exploded over Madeira's lawn and pool.

When Healy called back later, Madeira's friend and insurance agent, Michael Starr, was over inspecting the damage to the chimney. "How's it feel to be a multimillionaire?" Starr heard Healy say. "Doesn't it feel great, Al?"

Through a combination of trades, Madeira's $1 million investment had turned into $39.5 million, Healy said. Madeira was stunned but excited. So was Starr: Just the week before, he had wired $100,000 to Shalese's account to be traded through Healy. Documentation was sparse, but Madeira figured he had known Healy for ten years.

Seeing his investment multiplied by 40 excited Madeira. He wanted to push more money into the investment, but he was out of cash. Then again, Starr had clearly seen the draw in investing with Healy; if this friend or that friend would lend Madeira $1 million now, Madeira could easily offer a return of $3 million within 90 days. He would have his lawyer draft documents. Healy explained that there were restrictions on the account at the moment — some silly misunderstanding — but that they would be lifted February 1 or for sure by February 11.

In truth, the money had been long gone. Healy had spent more than $600,000 on 12 watches — Paris Hiltons, Hublots, a Rolex. He spent just as much money on a single ring: $619,000 for 162 diamonds and a simple band.

For wheels, Healy and Shalese had their pick of a $1.9 million fleet: a red Ferrari F430 Spyder, a yellow convertible Lambor­ghini, a black Bentley, a classic Porsche, a newer Porsche, a metallic burnt-orange Hummer golf cart. Healy had the interior of a 2008 Lamborghini turned pink; the logo decals had been replaced with rhinestones, and pink rims were installed.

Full-time bodyguard and Iraq veteran Tim Cash would drive the couple in a stretch Hummer limo while they bar-hopped their way through South Beach, sipping champagne at strip club Solid Gold or dropping $4,600 at Nikki Marina in Hollywood.

A typical style at Lezlie's Hair Studio or dinner at Hollywood Prime rang up at $500. They had box seats for the Panthers. They had box seats for the Heat. They paid their interior designer, Perla Licci, in sporadic installments of up to $65,000, for a total fee of $1.2 million.

In the same week that they spent $51,000 on the use of a private jet, the Healys dropped $1,000 at a swimsuit store, $10,000 at Versace, at least $100,000 on Bahamas resorts.

Shalese found their trophy case the day she toured a Weston home formerly owned by retired Dolphins quarterback Bernie Kosar. The seven-bedroom mansion in the Weston Hills Country Club was perfect, she told Healy. "If you like it, we'll get it," he replied — sight unseen. They paid $2.4 million for it on October 20.

The mansion would see another $2.3 million in upgrades: gold-leaf ceilings crowning silk curtains shading Versace windowpanes, Batman statues, full-sized Egyptian sarcophagi, and custom woodwork in the children's rooms depicting hand-painted ballerinas and superheroes.

The wet bar kept an eye on the pool table in the game room, where jerseys signed by Brett Favre and helmets autographed by Joe Namath lined glass cases. In the $500,000 home theater, lights twinkled like stars on the ceiling over red leather seats. Former Dolphins defensive end Jeff Cross could often be found fixing himself a drink, lounging on the couch.

The week after Healy called Madeira a multimillionaire, the chiropractor made the journey to South Florida for Shalese's baby shower. "I had no idea about the strip clubs and liquor — he basically said that he drank little to none," Madeira says.

At the shower, Madeira sat across from Dennis Rodman, the flamboyant former NBA player who lives in South Florida. "I feel good karma from you," Rodman said.

"Thanks, I guess," replied a confused Madeira.

"It's good, man," Rodman said. "It's good."

Before Madeira returned to Pennsylvania, Healy took him aside. "If anything ever happened to you, Al, I'll make sure I watch after your family, if you would do the same for me," Healy said. "You never know what you're going to get into."

"Of course," Madeira said.

Back home, Madeira continued borrowing money from friends and colleagues. Shalese's baby arrived that September, just before the economy crashed. That December, Bernie Madoff was arrested for running a $65 billion Ponzi scheme.

"Can you believe that guy?" Madeira asked Healy.

"The guy deserves the chair, Al," Healy replied. "I can't believe anyone would take people's money, give them false documents, and just spend it. He makes me sick."

Healy had promised that the restrictions on their account would be lifted by February 11. But when the day arrived, the money did not. There had been another hold, Healy explained. There was another restriction. It's coming, it's coming. By then, Healy had sworn that his and Madeira's cash position stood at a combined $160 million. Look, it's coming.

It didn't. Now it was supposed to be the beginning of March. Madeira called Healy three times on March 5. Each time, Healy hung up on him.

The friends who had lent to Madeira were beginning to feel that it was a scam and that perhaps Madeira was in on it. "Sean, I can't wait anymore," Madeira told him over the phone. "I apologize, but I have to contact an attorney over this."

Madeira hired Paul Turner. Healy hired attorneys, who told Turner that Madeira's money had been lost in bad investments.

"But I still have personal wealth myself," Healy said. "I feel bad for Madeira, and I had no idea other people were involved." Of course, Healy had spoken with, met, and accepted wire transfers from the other investors. Healy offered Madeira about $6 million to settle up, which Madeira was interested in — if Sean could show documentation that the money was traded.

Madeira flew to Florida for an in-person meeting with the man who lost his millions and their attorneys. But the meetings kept getting pushed back. On the last day Madeira was in town, Healy's attorneys said the meeting was off.

So on March 16, Madeira sued Healy in federal court for the $14 million he had invested. Madeira asked a judge to freeze Healy's assets and force him to produce documentation of the trades.

At the April 2009 deposition, Healy stared at the brick wall and lied. Madeira had been careless, had wired monies too late, and that had put restrictions on their account.

Turner blinked at Healy. "So it's your position that whatever the amount is that Mr. Madeira sent to you, he should have sent more money?"

"Of course."

Healy provided Turner contact information for the New York trader who had supposedly put through the investments. Turner would soon discover that the phone number was disconnected, and the address Healy provided had never existed.

Healy offered Turner another phone number. It turned out that the number belonged to a pay-as-you-go cell phone that had been purchased in Weston, a few blocks from Healy's home — the same place where it was activated.

But the true mistake Healy made was tossing a stack of bank statements to Turner. They made little sense: Eight of the 12 pages from one month were duplicates, and pages were missing. And when Turner sent the documents to a Post Office inspector with a background in fraud, the man laughed. The papers had clearly been doctored. They were fakes.

On July 12, the Securities and Exchange Commission filed charges in Pennsylvania against Sean Healy: two counts of wire fraud and one count of unlawful monetary transactions. Shalese was named a relief defendant, meaning that the government would come after anything she owned that was bought with the stolen money.

"I believe that she was complicit in everything Sean did," Turner says.

At the April deposition, Shalese said the Lamborghini was an investor's car, despite the pink modifications. She said Sean told her he was flipping cars with a partner from a dealership. She'd even seen the boxes of T-shirts and business cards with the company name: Fast Motor Sports.

The SEC appointed a receiver, Miami attorney Melanie Damian, to freeze the Healys' accounts and seize their assets. Damian showed up at their home on July 13. Shalese was taken aback and scared. Healy, however, was fine. "Everything's going to be OK," he told her. "This is just a misunderstanding. We'll get everything back."

"He was actually giving a little tour of the house at some point, like here's this room, check out this jewelry, here's where we have our theater room," Damian says. "It was like he was showing off — who shows off to the receiver that's taking their things?"

Damian seized the hard drive of Healy's office computer, the one he swore he'd done all the trades on, and turned it over to the court. There were no trades.

Instead, the computer was filled with contracts for sports boxes and country club memberships and private jets, photos of their Lamborghini in stages of customization, pictures of the Versace goblets and dream cars and exotic linens.

With the accounts frozen, Shalese didn't have money to buy diapers.

At a deposition August 20 in Miami, Turner told Shalese to look at two sets of bank statements. He asked her if she noticed anything suspicious. She did. The bank's copies of the actual statements were different from Healy's sloppily prepared fakes.

Shalese walked out of the room and began to cry. "What's going on?" she asked.

She climbed into the car with her husband, who immediately said, "Don't worry about it. We knew about that. It's all going to be fine."

A few days later, Healy called Shalese into his office, a wedding of marble and granite. From his desk chair, Healy had a direct line of view to the desk of his bodyguard, and behind him was a touchscreen that let him scan security cameras that covered every inch of his 100,000-square-foot mansion. To his right, he could see through the hallway window to his circular driveway, past the fountain he'd had custom-installed, to anyone entering his home. From this spot, he could see anything coming at him.

"Look," he told Shalese, "I don't want to scare you. But there have been threats against you and the kids."

A third party, "a really bad guy," had run off with all the money Healy and Madeira had invested, he explained. Maybe it was the fictional Matt or a man named Mike Hein or whatever — but he was gone, and he had called Healy. The man said he'd kidnap Shalese and the kids and kill them.

Shalese and Sean decided to take the kids to visit Healy's mother in New York. While they were en route, cops showed up at the Weston mansion looking for Healy. On October 15, he reported to the U.S. District Court in Harrisburg, Pennsylvania. One night, when Healy was away at court and his parents had gone out of town, the power went out. It wasn't storming. The weather was fine, clear. Shalese and the two kids were alone in the house, and suddenly, she knew: The bad person had come for them.

Her children's hair was still wet from their baths, and they were all barefoot. She felt around for her keys, and they ran, sobbing, out the front door. Shalese locked herself and the kids in the car in the driveway. She called the police, trying to explain. They came. A circuit breaker on the street had blown.

On November 23, Healy pleaded guilty to the wire fraud and unlawful monetary transactions charges. Twelve days later, U.S. District Court Judge Jose Martinez in Miami awarded Madeira a $48 million civil judgment against Healy and Shalese. Anything bought with the stolen money was to be sold, and the investors would split the proceeds. But it will be only a fraction of the money they put in. Healy and Shalese would always owe the rest of the money.

At his criminal sentencing on March 31, Healy stood up in courtroom number three on the eighth floor of Harrisburg's Federal Building and wept.

"I'm very sorry for everything I've done. I really messed up," Healy told U.S. District Court Judge Sylvia Rambo. "I know everybody here has children, they have problems, things like that, because of what I created. I have four kids at home. They don't deserve it. I did a really bad thing.

"I'm not a con man by any stretch of the imagination," he trembled. "I'm a family man. I have kids."

Madeira was there. "I'm hoping it was sincere, but he's a professional actor, second only to Madoff. Who knows? Who knows his heart? Who can have you over at his house, have barbecues with the kids, have you out to dinner with his parents — who does that? Who takes advantage of you and acts like he's your best friend? He begged me to be the godfather to his daughter. Who does that?"

Turner didn't buy it. "In my opinion, you've been running cons your entire adult life, and you go to prison... He's just going to come out with new tricks."

Judge Rambo sentenced Healy to 188 months — nearly 16 years — in prison.

Shalese wasn't there. It was too expensive, she explains. She was living with an old friend in Hollywood, working as a bartender five nights a week. It didn't make sense to skip work, get a sitter for the kids, buy a flight, pay for a hotel room, just to sit in a courtroom for one day, she says.

"A lot of people say, 'He did this because of you' or 'He wanted to give you these things,' " Shalese says. "I've never had somebody love me that much." She pauses. "If it was so much that he felt like he needed to do this, I don't know. But it was never like I expected any of this. I was happy with him in a modest house without all the jewelry."

Sitting in a Pennsylvania jail cell awaiting his appeal, Healy has time on his hands. He sends the kids word puzzles and drawings of Cookie Monster and Superman. He sends Shalese three letters a day, some eight pages long, front and back.

And he calls, all day. After the first time, Shalese will turn her ringer off. She reads his letters sporadically. "I need to stay in a positive place and be positive for the kids and be going to work every night," she says. "To sit and read those things all the time, it brings you back."

But when she does pick up the phone, Healy tells her the same thing every time. He loves her and he misses her. He needs her to be there for him. To promise that they'll always be together.

He's going to take classes in prison. He's going to get a new degree, to support her when he gets out. He misses the kids. He loves the kids.

He's going to make this better.

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