Bad luck can come in many forms. We often think of it as being a sudden illness, a tragic accident, or losing a job. However, for lottery winner Jack Whittaker, bad luck came in the form of winning a huge $315 million Powerball jackpot.
Almost a Christmas miracle
In 2002, the Whittaker family of Charleston’s Scott Depot suburb was a West Virginian success story.
According to a detailed article published by The Washington Post, the family patriarch, Jack, had lifted himself out of poverty to become the highly successful owner of a sewer-and-pipe-laying construction business.
At 55, he worked hard to provide a good living for his wife, his widowed daughter, and his beloved granddaughter Brandi.
Jack enjoyed moderate gambling and made a habit of buying a Powerball ticket if the pot got bigger than a hundred million.
On Christmas 2002, his wife Jewell, watching late-night TV, thought that Jack’s ticket matched four numbers of five. The couple went to sleep with visions of a six-figure windfall dancing in their heads.
In the life of a working man, 4:30 a.m. is time for a deep yawn and a blind stumble to the coffee-pot. It’s not usually time to turn on the TV.
However, on December 26th Jack made an exception to see if his wife had been right.
She was wrong. He had five matching numbers, winning what was at the time the biggest undivided jackpot in history.
Jack Whittaker’s good intentions…
Jack’s initial reaction to winning an unprecedented $315 million in the Powerball lottery was everything that could be hoped for.
He was joyful, humble, and openly generous.
He gave the deli worker at the gas station where he’d purchased the winning ticket a hundred dollars cash. Shortly afterwards, he bought her a house in his own neighborhood and gave her a large cash bonus.
He pledged to tithe a Biblical ten percent of his winnings and promised to open a foundation to help the many needy people in his community.
At first, he made good on these larger-than-life promises. The foundation opened, and Jack gave out of his own pocket to many down-and-out folks that tracked him down in person.
However, the burden of national fame and local notoriety in his largely poverty-stricken community quickly became overwhelming.
Everyone seemed to think that Jack owed them something. News agencies wanted his story. Friends and family wanted hand-outs. Do-gooders thought some of that good fortune should be thrown their way. And parents of children with cancer thought they’d found a savior.
A series of unfortunate events
The Washington Post reported that just a week after his initial big promises to help others with his lottery bonanza, Jack walked into a local strip club and put $50,000 cash on the bar.
“It was like the money was eating away at whatever was good in him,” Misty — a type of den-mother/problem manager at the strip club — said. “[The money] just consumes you. You become the money. You are no longer a person.”
Jack was such a problem that the Pink Pony club where Misty worked had to assign a bodyguard to protect the girls from him. The manager repeatedly begged him to stop flashing cash, fearful he’d “get rolled at the club.”
Despite these warnings, one night Jack was robbed of $545,000 cash from his car in the Pink Pony’s parking lot. Two employees were charged, though never indicted, and the club lost its liquor license.
Jack had gone from a man who gainfully employed over a hundred people to a man who’d cost dozens of people their livelihoods in one night.
By the first anniversary of his “win,” Jack estimated that he’d already gone through $45 million of his windfall.
Jack recklessly continued to frequent strip clubs, trashy bars, and racetracks, where he quickly became a pariah. His “patronage” was a type of poison, breaking up long-standing relationships, causing fights, and closing doors permanently.
He also continued to get robbed in one way or another, sometimes at gun point. Jack was involved in several one-vehicle accidents. He drank heavily and was charged with driving under the influence. Women sued him for harassment and molestation.
Eventually a casino in Atlantic City sued him for racking up gambling debts of $1.5 million.
In just five years after his jackpot win, the $315 million Powerball winner claimed his bank account was empty.
Family pays the highest price
Worse than all the blown money, wasted opportunities, and selfish destruction of other people’s lives was what the money did to the Whittaker family.
Poor Jewell, who’d loved her husband of forty years, separated from him.
His daughter Ginger blew money revamping a mansion. She made sure it included a special suite for her teenage daughter Brandi, the apple of the family’s eye.
Jack, the over-indulgent Paw-Paw, purchased his granddaughter four custom cars and gave her $2,000 a week to spend as she wished.
Brandi quickly spiraled out of control. Within months, she was involved in a series of bad relationships, all revolving around her willingness to buy “friends” with insanely expensive presents. Mostly, her world became drugs.
Her most serious boyfriend was found dead of an overdose in Jack’s home in 2004. A few months later, just two years after the lottery win, Brandi was also found dead.
The 17-year-old was wrapped in a plastic tarp and dumped behind a decrepit van at a place called Scary Creek. In this ABC News interview, Jack discusses the loss of his granddaughter and how the lottery money was a curse for him and his family:
By 2009, Brandi’s mother Ginger was found dead in her home, of unspecified but unsuspicious causes.
Finally, Jack’s uninsured home — the place where it all started — burned down in 2016. Jack lived another four years, passing away in 2020 of natural causes.
Reflections on the tragedy of winning
Jewell often said that she wished she’d just torn up that ticket. The money ruined their lives. And while Jack never accepted responsibility, he did say in one interview that he also blamed the accursed money.
It’s easy to sit in judgment on Jack Whittaker. “If I won a massive jackpot, I’m sure I’d do better.”
But would I? Would any of us?
Henry Ford famously said: “Money doesn’t change men, it merely unmasks them. If a man is naturally selfish or arrogant or greedy, the money brings that out, that’s all.”
Navigating a windfall: Lessons from Jack Whittaker’s story
In many ways windfall wealth is a test. It’s a test of your character, your ability to manage change, your moral beliefs, and whether you’re reactive or proactive, in your life.
Character and moral beliefs
Prior to his tragic win, Jack was a self-professed Christian. However, given the train-wreck which so quickly followed, it would appear that some of those beliefs were only skin-deep.
Presented with the sudden freedom of having “more money than God,” he slowly lost all sense of self-restraint.
His total lottery win—$113,386,407.77 after taxes—is a massive chunk of change. However, it’s not more money than even the federal government, much less God.
It’s also interesting to note that Jack’s hill-raising had been a rough-and-tumble philosophy of “Don’t start a bar fight, but never lose one.” Jack’s wild behavior in bars and strip clubs seems almost to have been begging for someone to punch him out. But no one’s going to rough up the local millionaire, leaving him without external boundaries.
Managing change
Another mistake Jack made was in believing that he could accept that kind of money and nothing would change in his life. Any kind of windfall will change your life to some extent. The larger the dollar figure, the greater the change.
First off, anyone who receives windfall wealth should seek professional legal and financial advice to prepare a good plan for their new financial circumstances. If Jack had such a plan in place, it doesn’t appear that he followed it.
Another wise decision would have been a change of address.
Much as Jack and Jewell loved their rural community, the money made it impossible for them to continue in their original lifestyle. And the harder they tried to force it, the more they poisoned the lives of those around them.
Much like a superhero, privacy is the best protection a person with money can have.
Whether that means moving to “rich country,” behind gates and security guards, or simply disassociating your identity from your net worth, you can’t live with people who resent you because you’ve got more than they do. It’ll destroy your peace of mind, and it’ll destroy anyone who feels like you owe them.
If you’ve recently received a windfall, or if there’s a possibility that you might, make sure you figure out how you’re going to protect your privacy, safeguard your new wealth against scammers, and wisely handle your wealth.
One good way to do this is to look at the habits of the wealthy.
Especially people who’ve made their own money and have kept it longer than ten years.
- How do they invest?
- How do they give?
- How do they handle publicity?
Proactive versus reactive thinking
Jack’s thinking was all reactionary, start to finish.
He reacted to his sudden wealth out of an instinctive desire to give and help his community. Nice goals without any specific direction.
One common factor shared by proactively wealthy people is their focus. They focus in on one or two goals in any given area and pour their energy into that. Most people who stay rich are incredibly generous. However, you’ll notice that they pick just a few causes with which they have emotional ties to focus the bulk of their generosity.
Jack created the “Jack Whittaker Foundation” to give money away to people who needed it. Not surprisingly, the foundation was quickly overwhelmed and had to shut their doors.
He might have considered creating:
- “The Jack Whittaker Foundation for Lymphoma,” (a disease his daughter suffered from)
- “The Foundation for Suicide Prevention,” (to which he’d lost his son-in-law), or even,
- “The Jack Whittaker College for Small Business Success”
He showed the same short-sightedness in giving to his beloved granddaughter. Without a plan for how her life might have been made truly better, he literally spoiled her to death.
A cautionary tale
Sudden windfall wealth is both a deep desire, and a secret terror, of many of us because of stories like Jack’s.
On the one hand it shows that — rare as it might be — winning a mega-jackpot is possible. And on the other hand, these success stories that turn into tragedies show that rich people aren’t protected from life’s most painful consequences.
In some ways, they’re more vulnerable.
Jack started as a remarkable success by the standards of his West Virginia community. He was an independent businessman, reasonably affluent, and had a thriving family.
Only 17 years after winning $315 million, his life, family, home, and legacy were in literal smoking ruins.
He and his broken-hearted wife had a bitter divorce. Both his daughter and granddaughter died before him. He left a string of ruined lives behind him.
Forensic accountant Bob Rufus, who was brought in during the divorce and witnessed the disaster first-hand summed up the Whittaker Powerball tragedy:
“What happened to Jack would be humiliating to a normal person. But he felt like he was above it all as a result of financial worth. [Winning the lottery] certainly wrecked his life.”