January 16, 2003: Jack Whittaker was arrested for drunk driving.
August 5, 2003: thieves broke into his car while it was parked at the Pink Pony, a strip club in Cross Lanes, West Virginia. The thieves went away with $545,000 in cash. Two employees at the same club, the manager and dancers manager who were romantically linked, were later arrested and charged with a plot to put drugs in Whittaker's drinks and then rob him.
January 25, 2004: thieves once again broke into his car, this time making off with an estimated $200,000 in cash that was later recovered.
January 6, 2004: Whittaker was arrested for misdemeanor assault after allegedly threatening the life of a bar manager in St. Albans, West Virginia.
He has also been sued after allegedly groping a woman at a dog racetrack. Whittaker told a TV station after he was charged with drunken driving, "It doesn't bother me because I can tell everyone to piss off."
September 2003, Jesse Tribble, a 17-year-old on and off again boyfriend of Jack's granddaughter Brandi Bragg, was found dead in Whittaker's home in Teays Valley, West Virginia. A coroner's report indicated that he died of a drug overdose.
December 20, 2004, Brandi, 17, was found dead after a drug overdose. After she had been missing for several weeks, her body was discovered lying under a tarpaulin near her then boyfriend's home.
May 27, 2005: Jewell Whittaker (wife) filed for divorce on in Raleigh County, West Virginia.
Whittaker is also being sued by Caesars Atlantic City casino for bouncing $1.5 million worth of checks to cover gambling losses. Whittaker is also countersuing them, claiming that his losses were supposed to be credited due to a slot machine he developed and that they in fact owe him money.
January 11, 2007, a legal complaint against Whittaker alleged that Whittaker claimed that on September 11, 2006 thieves took all of his money. The robbers, according to the account, went to 12 branches of the City National Bank and cashed 12 checks. The incident came to light because Whittaker had not been paying money to a woman who had previously sued him. Kitti French filed the complaint earlier in the week, requesting court costs and money from Whittaker.
On March 26, 2007, Jack Whittaker settled a wrongful death civil suit. The unexpected deal came not long after Whittaker was questioned about whether his money and alleged lack of supervision contributed to the death of 18-year-old Jessie Tribble. Whittaker defended providing his granddaughter, Brandi Bragg, with a $2100-per-week allowance. James Tribble alleges an un-parented Bragg funded the drug purchase that let his 18-year-old son Jessie die of a drug overdose in Whittaker's house.
On February 27, 2008, Whittaker had a "near-miss" $10,000 Powerball win (missing one of the five regular numbers, although he did match the red Powerball number.)