Biggest Lottery Losers: Jack Whittaker’s Tragic Powerball Win

Winning the lottery will definitely change your life—but not always for the better, as Andrew Jackson “Jack” Whittaker, Jr. of Putnam County, West Virginia discovered. After winning the $314.9 million US Powerball jackpot in 2002, Whittaker suffered a string of personal tragedies that ruined his life and decimated his winnings. Just five years after he won, the once-lucky Whittaker told an interviewer that he wished he’d “torn that ticket up.” Here’s how he became one of the biggest lottery losers in history—and how the tragedy could have been avoided.

HOW JACK WHITTAKER WON THE JACKPOT

Before his fateful win, Jack Whittaker was the president of a successful water and sewer-pipe laying firm in Putnam County, West Virginia. He had an estimated net worth of about $17 million before he bought the winning lotto ticket. He lived a simple life, getting up at 4:30am daily to run his company, and he spent his spare time with his family. With plenty of cash in his pocket, he wasn’t a regular lottery player—nor did he need to be.

However, by Christmas Day in 2002, the US Powerball jackpot had ballooned to a massive $314.9 million prize, so he decided to buy in. Whittaker purchased $100 worth of Quick Pick tickets at the deli where he bought his breakfast biscuits every morning. The next day he woke to the world-shattering news that his ticket was the winner!

Even more impressive, he was the only winner. At the time, Whittaker held the record for the biggest American jackpot claimed by a single ticket.

America’s luckiest man decided to take the cash payout and pocketed a hefty $170 million prize.

HOW WHITTAKER SPENT HIS WINNINGS

Jack Whittaker was a generous man, and his first move was to donate 10% of his winnings to local charities and churches. He also invested $14 million in a new charity he named the Jack Whittaker Foundation, which gave food and clothing to needy families in his economically struggling home state.

Whittaker appeared in newspapers, on television interviews, and local morning shows—and the more money he donated, the more famous he got. His wife and granddaughter were often pictured with him. 

Finally, he went back to the deli where he’d purchased the lucky ticket. He had been buying his breakfast from the friendly manager, Brenda Higginbotham, for years, and they got along famously. One day he simply showed up and gifted her a generous $44,000 cheque—and went on to buy her a$123,000 home and a new Jeep Grand Cherokee SUV.

WHERE IT ALL WENT WRONG

Many lotteries around the world encourage winners to remain anonymous, but only eight American states allow anonymity. West Virginia isn’t one of these states, and Whittaker’s public win and extreme generosity became a serious problem almost immediately.

Soon after his win, calls and letters from strangers began pouring in, asking for money. He got mail asking for help to pay for medical procedures for sick family members, for investments, and for donations to religious causes. Locals began stalking him and his wife, waiting at the deli where he bought his breakfast and begging him for jobs. He began receiving threats and had to hire private security for his family.

The attention and money eventually became too much for Whittaker. He began gambling, drinking, and spending wildly. This was not wise in West Virginia, where many communities are living in poverty—and tragedy soon followed.

A STRING OF ROBBERIES AND TRAGEDIES

Just eight months after winning the Powerball, Jack Whittaker had made a name for himself as a party animal at local bars, the horse track, and strip clubs. One day, he visited a local club and told the entire bar that he had a briefcase stuffed with $545,000 in cash in his car, which he had left running by the front door.

By the end of the night, someone had allegedly tried to drug him, and his briefcase was gone. Police later located it behind the dumpster of the club. The club’s owners were charged with robbery, but they were never indicted.

While he was spending wildly, Jack Whittaker also regularly gave thousands of dollars in spending money to his 15-year-old granddaughter, Brandi. Unfortunately, easy access to huge sums of money corrupted her friendships and she began using drugs to cope with the loneliness. Whittaker then began paying people to spend time with her and allowed them to drive her around in his luxurious cars.

Within just two years of winning the lottery, Whittaker’s car was also broken into and $100,000 was stolen; a woman he was having an affair with was robbed of $25,000 and one of his cars; and a friend of Brandi’s overdosed on drugs and died at one of his houses. Adding to this chain of tragedies, Brandi also overdosed and passed away in 2005 at the tender age of 17. Jack Whittaker blamed Brandi’s friends for giving her the drugs.

In 2009, Whittaker’s daughter, Ginger, also passed away after succumbing to the cancer she had been battling for years.

In the intervening years since his win, Whittaker has racked up a mountain of debt and legal trouble. He was called to court for a DUI in 2003 and was ordered to attend rehab for his drunk driving charge. He was also sued by a casino worker named Kitti French, who stated that he had assaulted her. She won the case, but Whittaker claimed that he couldn’t pay her because thieves had emptied his bank account. The bank investigated this claim, but the findings have not been made public. Whittaker was also sued by Caesars Atlantic City casino for attempting to cover $1.5 million in gambling losses with bounced checks.

More recent news about the Whittakers is no less disastrous. In December 2016, a massive fire broke out in their home and everything was destroyed, but luckily the couple survived. Unfortunately, the home was not insured.

DEATH

On June 27, 2020, at the age of 72 years old, Jack Whittaker passed away after a battle with an undisclosed illness. He left behind his wife and two remaining daughters.

CONCLUSION

Unfortunately, Jack Whittaker’s family and neighbours experienced what can happen when an unimaginably huge jackpot is let loose in a small, economically depressed community. While Whittaker may still have some of his $170 million in winnings remaining, the exact amount is not clear—and he certainly lost what mattered most: his daughter and granddaughter.

Whittaker’s string of personal tragedies and financial disasters emphasizes the extreme importance of setting up sound financial and legal management for a lottery windfall, curbing one’s personal spending habits—and safeguarding your loved ones. Like so many other lottery winners who lost it all, Jack unfortunately learned this the hard way.