How Winning $314 Million in the Lottery Ruined His Life

By Stuart Wolf - May 25, 2025

This article appeared in peekably.com and has been published here with permission.

Nearly everyone dreams of winning the lottery, but be careful what you wish for! Jack Whittaker from West Virginia thought he was the luckiest man in the world when he won a mega Powerball jackpot. But as soon as the millions hit his bank account, Jack went off the rails, and his life fell apart. This is the story of how winning $314 million on the lottery ruined Jack’s life.

Who Is Jack Whittaker?

Andrew Jackson Whittaker Jr. was born in the small town of Jumping Branch, West Virginia, on October 9th, 1947. As you may already have guessed, his father was Andrew Jackson Whittaker Sr., while his mother was Ruby Christine Upton Whittaker, née Upton.

Photo via Reddit

Jack was a normal West Virginian kid who married his high school sweetheart, Jewell, almost as soon as they graduated in the 1960s. Jack loved country music — especially the music of Johnny Cash — and pretty soon, he started dressing like The Man in Black.

Family Man

After tying the knot so young, Jack formed his own construction company from the ground up. Over the years, Jack and Jewell had a son, Dion, and a daughter, Ginger Whittaker-Bragg. A hard worker, Jack worked his way up to president of Diversified Enterprises Construction, his contracting firm in Putnam County, West Virginia.

Pexels // Yury Kim

Even before his lottery win, Jack was already a rich man. Early mornings, long hours, hard work on construction sites, and running his own business had brought him home a whopping $17 million.

One of the Locals

55-year-old Jack Whittaker was well-known around Putnam County for being a self-made man, a construction company owner, and for his stylish appearance and cowboy hat. He always dressed in a sleek country style, which led many locals to compare him to his hero, country musician Johnny Cash.

Wikimedia Commons // Tim Kiser // Public Domain

Like most people in the area, Jack drove a truck, lived in a modest home, and often stopped at his local convenience store for deli sandwiches, a coffee, and a chat.

‘Twas the Morn Before Christmas

That local convenience store was C&L Super Serve in Hurricane, West Virginia. The cashier there described him as being “polite and cheerful as if trouble were a stranger.” Just before 6:30 a.m. on Christmas Eve of 2002, the store’s Biscuit Lady — 39-year-old Brenda Higginbotham — noticed her favorite customer pulling up outside the store.

Facebook // @C&L Super Serve

So, just like every other day, Brenda began preparing his usual breakfast order. She liked Jack as he always made her feel happy and put a smile on her face.