The High Cost of Winning

updated 03/15/2004 AT 01:00 AM EST

originally published 03/15/2004 AT 01:00 AM EST

Jay Sommers, 36
Won: $5.8 million
Outcome: Lost it all, delivered pizza

Oh, to be young, handsome and suddenly so rich you can outshop Paris Hilton! Jay Sommers was 20 when he won a fifth of a $28.9 million lottery jackpot in Michigan in 1988. With his first annual $290,000 payment he bought not one but five new cars. "I blew all of the check in 2½ months," says Sommers. "What 20-year-old wins that kind of money and is sensible with it?"

Oh, to be young, handsome and suddenly so broke you're delivering pizza! Spending so fast he couldn't pay taxes, Sommers asked a friend who is a businessman to manage his loot. His pal persuaded Sommers to swap his annual checks for a discounted lump-sum payout. One day in the mid-'90s Sommers went to the bank and discovered all his money was gone—frittered away by his friend's bad investments and shady deals. Sommers sued his friend and won the case, but spent much of his $887,000 settlement paying off lawyers and debts. To make ends meet during the case he took the pizza-delivery job. "People recognized me and it was humiliating," says Sommers, 36. "One minute I'm famous and five years later I'm broke. It's been a roller coaster ride."

Single and living near Detroit, Sommers now does construction work and is a racecar driver trying to make it big in NASCAR. "I'm still bitter and I'll be bitter the rest of my life," he says. "I think I'd be further along today if I had never won."

Callie Rogers, 17
Won: $3.5 million
Outcome: Lost fiancé, peace of mind

After supermarket clerk Callie Rogers, then 16, bagged her jackpot last June, "I just sat there crying," the British teen recalls. Over the coming months there would be more tears in store. First, jealousy reared its ugly head. "People I didn't know were saying bad things about me," she says. Then her 25-year-old boyfriend proposed—and told her she'd have to buy her own ring, promising to pay her back. She ended up dumping him. "I knew he was a loser before I got rich," she says now.

These days things are looking brighter for Rogers. She has a new, live-in boyfriend, 24-year-old Nicky Lawson. "He's got his own money," Rogers says. "He bought me my ring."

Andrew 'Jack' Whittaker, 56
Won: $314.9 million
Outcome: Embarrassing busts, stolen bucks

As Andrew "Jack" Whittaker should be able to attest, tippling and toting around large stashes of cash don't make for a winning ticket. Since bagging the largest single Powerball jackpot ever on Christmas Day, 2002, a lump-sum windfall of $113.4 million after taxes, the married contractor from Scott Depot, W.Va., has survived a series of misadventures that sound like something from The Sopranos. During the past eight months Whittaker, 56, has been drugged at a strip club and robbed of $545,000 (it was recovered); arrested for threatening to have a bar manager and his family killed (he faces a March court date); and charged with drunk driving after state police found him sitting in his Cadillac SUV on the side of the interstate on Jan. 25, allegedly slumped over the wheel with the vehicle running. Said Whittaker, whose blood-alcohol level registered 0.190, twice the legal limit: "I wasn't driving, absolutely wasn't driving."

Many locals seem inclined to view Whittaker's troubles tolerantly, however, especially since he earmarked $14 million to establish a foundation that delivers food, clothing and scholarships to the state's poor. "I just keep on doing what I'm doing," Whittaker said after his DUI arrest, "and tell everyone my personal life is my own business."

Billie Bob Harrell Jr., 50
Won: $31 million
Outcome: Lost his marriage—and his life

Billie Bob Harrell Jr. was just about broke when he played the Texas Lotto Jackpot in June 1997. But then six ping-pong balls landed the right way and Harrell, 48, was $31 million richer. He quit his job at Home Depot and with his first $1.24 million check took his family to Hawaii, gave tens of thousands to his church, lavished cars and houses on friends and family. He even bought 480 turkeys for the poor. "He played Santa Claus," says his mother, Agnes. "He seemed to think everything would be all right. But it never was the same again."

Suddenly strangers were calling demanding donations; Harrell changed his phone number several times. The strain of it all damaged his marriage, and less than a year after winning Harrell split from his wife. Reckless spending and lending led him to make a bad deal with a company that gives lottery winners lump-sum payments in exchange for their annual checks, and Harrell wound up with much less than what he had won. But by then, it seemed, all he wanted was to have his family back. One night in 1999, just before he was set to meet his ex-wife for dinner, his oldest son found him dead of a shotgun wound. "Winning the lottery," Harrell had earlier told a friend, "was the worst thing that ever happened to me."

Today Harrell's mother does not believe her son took his own life, despite a police report ruling it a suicide. In the bedroom that night police found a note they believe was meant for his ex-wife. "I didn't want this," Harrell wrote. "I just wanted you."

Denise Rossi, 53
Won: $1.3 million
Outcome: Stripped of her winnings

Blindsided—that's how Thomas Rossi felt when Denise, his wife of 26 years, hit him with divorce papers in 1997. "I thought we got along good," says Rossi, 70, a photographer. "I couldn't understand it. She wanted me to move out of the house very fast. It wasn't like her to act this way."

Two years later it all made sense. A letter addressed to his ex-wife that mistakenly arrived in his new Los Angeles apartment revealed she had won a lottery. Rossi learned Denise had scored $1.3 million in the California lottery on Dec. 28, 1996—11 days before she filed for divorce. He took her to court for not disclosing the money, and the judge awarded Rossi the entire haul. According to her lawyer Connolly Oyler, Denise could have kept half and perhaps all of her loot had she been honest, but the court ruled "her failure to disclose was a fraud," he says. Since then Denise has disappeared (she could not be located for comment), but not before trashing Rossi. "I was very happy to be free of this person that was like a parasite," she told NBC's Dateline in 2000. "[Winning the lottery] has brought me really nothing but grief and headache."

Receiving $48,000 after taxes every year, meanwhile, has given Rossi "peace of mind," he says. "If it wasn't for the lotto, Denise and I would probably still be together. Things worked out for the best."

William Post, 64
Won: $16.2 million
Outcome: Brother hired a hit man to kill him, divorce, bankruptcy

Gone are the days when William Post, 64, would find a pair of pants he liked and buy 400 of them. Gone too are the mansion, the farm, the half-dozen cars and the diamonds. In fact, looking around Post's ramshackle home in Franklin, Pa., you'd never suspect that 16 years ago he won $16.2 million. And yet despite declaring bankruptcy in 1994 and suffering from health problems including severe asthma, Post maintains, "I'm a very happy man now. Money can't buy peace of mind."

As an overnight multimillionaire, that was certainly something that eluded the onetime circus cook. In 1994 his brother Jeffrey pleaded no contest to hiring a hit man to kill Post and his then wife, Connie, allegedly in order to get his hands on Post's estate. (Jeffrey is serving 20 years probation.) Spooked by the plot, Connie left Post not long after. From there things deteriorated further, in large part because of Post's lavish and sometimes bizarre spending sprees. "As soon as the stores opened he'd want to go and buy stuff," says his daughter Gladys Burrous, 42. "Everything, anything."

Today Post lives on a $558 monthly Social Security disability check and has $43 in the bank. "He probably is happier," says Burrous of her father. "When he won, he really didn't know how to handle it."

Pam Lambert and Alex Tresniowski. Andrea Billups in Washington, D.C., Lauren Comander in Chicago, Kathy Ehrich in New York City, Wendy Grossman in Houston, Ken Lee in Los Angeles and Ellen Tumposky in Cockermouth, England

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