Whittaker donated large sums to Christian charities, including the construction of a multimillion dollar church in Hurricane, West Virginia. He also set aside $14 million to start the Whittaker Foundation, which provides food and clothing to impoverished families in West Virginia. Whittaker also tipped a woman who worked at a local convenience store where he purchased the winning ticket by buying her a $123,000 house, a new trick, and $50,000 cash. So far, so good!

Unfortunately, Whittaker had a penchant for strippers and strip clubs. In 2003, thieves broke in his car while it was parked at the Pink Pony strip club in Cross Lanes, West Virginia. For some strange reason, Whittaker had over half a million in cash in his vehicle, and thieves made off with $545,000. At the time, Whittaker expressed concerns that the incident may affect his charitable efforts. Whittaker told reporters, "I'm simply a businessman who has seen his share of failures and successes. My personal life is my own, and I make no excuses for my actions." Thieves broke the driver's side window and stole a briefcase containing the cash. The briefcase contained $245,000, and thieves also stole three cashier's checks for $100,000 each.

The local sheriff weighed in and stated, "It's a known fact that Mr. Whittaker does carry a lot of money around with him, because he does frequent not only that club, but several other establishments... and he does gamble." Whittaker told police he was drugged, and provided police with a urine sample for analysis. As the old saying goes, a fool and his money are soon parted, and it wasn't long before Whittaker was back at the strip clubs. On January 25, 2004, criminals broke into his car and stole about $200,000 in cash. This time, the cash was recovered.

As the sheriff mentioned, Whittaker liked to gamble. Unfortunately, his luck at the gaming tables was abysmal. Whittaker was sued by Caesar's Casino in Atlantic City for bouncing $1.5 million in checks he used to cover his gambling debts. Whittaker also had a granddaughter he doted on and gave her large sums of money. On December 20, 2004, Brandi Bragg, his granddaughter, was found dead and her body was wrapped in a plastic tarp. The death was ruled an overdose, and the crime has never been solved. In 2005, Whittaker was charged with drunk driving, and his luck seemed to deteriorate with each passing year. Whittaker has said that he wished he had never purchased the winning ticket. He told reporters during an interview: "You know, my wife had said she wished that she had torn the ticket up. Well, I wish that we had torn the ticket up too."