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Around that time, Dippolito began a relationship with a woman named Karen Tanne. She was a recent South Florida transplant from Long Island who had a soft spot for Charlie Brown comics and worked for a nonprofit that advocated for children and families. In July 1998, Tanne gave birth to a son. A recent DNA test backs up her claim that Michael Dippolito is the father.
Soon after Tanne's son was born, Dippolito moved on to another woman: Maria Luongo, a smiling, brown-eyed girl from a traditional Italian family who would stand by him for years to come.
Meanwhile, Dippolito was introduced to the world of commodities fraud. He worked in a local boiler room, where he and fellow telemarketers would recruit people to invest in the foreign currency market and then steal the customers' cash. The Rubbo family, a Broward County clan with ties to the Bonanno crime family, was running this scam in Palm Beach and Broward counties. Investors lost $11.7 million before the scam was busted in 2002, according to a federal indictment.
It's not clear from court files which boiler room Dippolito worked in. Broward Sheriff's Office Det. John Calabro says it "may have" been the Rubbos'. But after learning the trade, Dippolito soon branched out to run his own scheme.
In 2001, he set up two companies — M.A.D. Financial and C.T.U. Inc. — and began cold-calling strangers as far away as Ohio, Illinois, and California, persuading them to invest in foreign currency. From an apartment in Boca, he'd extol the virtues of quick profits to be gleaned from the fluctuating exchange rates between the dollar and the Japanese yen, the euro, and the British pound. The plan was "risk-free," he told customers.
Sitting at home in Northfield Center, Ohio, investor George Nemeth thought the business opportunity sounded tempting and "glamorous." If he invested $20,000, he could earn a profit of $7,000 or $8,000 in a few months, Nemeth remembers a salesman from Dippolito's company telling him.
Already, Nemeth could picture the boat he would buy with the profits. "I almost sent more [money]," he says.
Nemeth was one of at least a dozen customers who wired money to Dippolito's corporate bank account in Jacksonville — some sent $16,000; one man sent $25,000. But soon, Nemeth realized he had been scammed. His phone calls to M.A.D. Financial were never returned. And of course, the profits never materialized.
Instead, Dippolito kept the cash. He splurged on hotel rooms, clothes, and jewelry. He spent more than $6,000 on "pay-by-the-minute chatrooms," including psychic and phone sex hot lines, according to a probable cause affidavit.
Nemeth called the U.S. Commodity Futures Trading Commission and discovered officials there were already aware of Dippolito's scam. In 2002, the commission filed a federal lawsuit alleging Dippolito's companies collected a total of more than $200,000 in about 11 months. (He was the sole officer and director of both companies.)
Calabro arrested Dippolito in March 2002.Dippolito pleaded guilty to charges of organized fraud, grand theft, and unlicensed telemarketing and was sentenced to two years in state prison — although he served only seven months, thanks to the time he'd already spent in jail awaiting trial. He was forced to make monthly restitution payments to his victims and remains on probation until 2032.
Those close to Dippolito believed he turned over a new leaf when he got out of prison. In July 2007, he launched an online marketing company called Mad Media Inc. and used a portion of his income to pay back his victims, according to Calabro. The detective thought Dippolito had been "doing what he needed to do to stay clean." Fraud victim Nemeth says he has received steady restitution checks for years — but they are for just $8 to $10 each month.
Luongo kept dating Dippolito despite his criminal activities. Even today, she says the man she fell for was a sweet, caring boyfriend who would never intentionally hurt someone. "There was nothing that he wouldn't do for me," says Maria, now 29. They married in 2007, after knowing each other for nine years. "He was a great husband." One Christmas, her parents' TV set was broken, so Dippolito bought them a new flat-screen to replace it, she remembers. "He always made sure other people were happy before he was happy."
Maria was aware of Dippolito's troubles with the law — she even stayed with him while he was in prison — but declines to comment about that part of his past. Clearly, however, there were some things she didn't know about her husband. Such as how exactly he made a living, for instance. According to court papers, he claimed to earn $87,000 a year from his marketing business. But it's difficult to tell how legitimate the business is. Mad Media Inc.'s website, madmedia1.com, has a rudimentary design with a picture of a bulldog at the top. "We are an outsourced media planning, buying, and strategy organization with proven experience in interactive direct marketing," the site says. "Our proprietary technology-based solutions enable real-time delivery of high-volume, targeted, qualified, and cost-effective leads as well as campaign optimization and management."
"I don't know anything about any of that," Maria Dippolito says.