There is no shortage of lottery winners who go broke—enough to fill many seasons of reality television—but there was good reason to think that Whittaker, a successful businessman whose journey from rags to riches was the product of self-reliance and hard work, would make good use of his new wealth. The idea that 10 years later he would wish he’d torn up his winning ticket and thrown away the pieces would have struck the man and everyone who knew him as nuts.
Jack Whittaker’s downfall began at the Pink Pony strip club in Cross Lanes, W. Va., a crenelated building with pink-frosted stucco walls and black glass doors. The club’s unsettling combination of girlish innocence and highway-access-road menace might serve as a metaphor for the lottery winner’s inner life. At approximately 5 a.m. on Aug. 5, 2003, Whittaker called the police from the parking lot of the Pink Pony complaining that he’d been drugged and that a substantial sum of money was missing from his Hummer. “There’s no confusion on the fact that he didn’t have all his faculties,” a police spokesman told reporters. Whittaker gave the police a urine sample for analysis, and his private investigator found $545,000 in cash behind a trash bin an hour later; the strip club’s manager and his girlfriend were charged with robbing Jack, but were never indicted. “I’m simply a businessman who has seen his share of failures and successes,” Whittaker told reporters. “My personal life is my own, and I make no excuses for my actions.”
Whittaker’s faith that he could handle his enormous lottery winnings with the same qualities of self-reliance, hard work, and aggression that had allowed him to master previous challenges was tragically misplaced. Less than three months after the incident at the Pink Pony, Whittaker was arrested after driving his Hummer into a concrete median on the West Virginia Turnpike. The arresting officer, M.J. Pinardo, reported that he smelled alcohol, but Whittaker refused sobriety tests and became “extremely belligerent.” The police found a small pistol and $117,000 in cash on Whittaker. “It doesn’t bother me, because I can tell everyone to kiss off,” he explained to reporters outside the local courthouse after his arrest. His reply to criticism of his gas-guzzling Hummer was equally succinct: “I won the lottery,” he said. “I don’t care what it costs.”
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The cost of Whittaker’s insouciance went up sharply the following year. On Jan. 25, 2004, according to a police report, he got drunk, parked his car in the middle of the street, went away, returned to find that $100,000 he had left on the passenger seat was stolen, and was charged with drunken driving when the police arrived. Vernon Jackson Jr., also from Scott’s Depot, was indicted on charges including breaking and entering an automobile and grand larceny, but it was also possible to imagine that Jackson had simply taken money Whittaker no longer wanted. After all, he’d left the cash out in plain sight on the passenger seat.
Later, Whittaker was arraigned on charges of trying to assault and threatening to kill Todd Parsons, the manager of Billy Sunday’s Bar and Grill in St. Albans, after previously being banned from the establishment. Further lawsuits followed. In March 2004, Whittaker was sued by a floor attendant at the Tri-State Racetrack & Gaming Center in Nitro named Charity Fortner, who claimed he’d forced her head toward his pants while he gambled at the dog track. The suit was settled out of court for an undisclosed sum.