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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 families: 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 net 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 a simple band with 162 diamonds.
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.