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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.