Dear Powerball Winner: Take Our Advice and Take the Annuity

[Tanuki]

52. Jack Whittaker, who won over 300 million, is another cautionary tale

https://en.wikipedia.org/wiki/Jack_Whittaker_%28lottery_winner%29

..."On August 5, 2003, less than a year after Whittaker won the lottery, thieves broke into his car while it was parked at a strip club in Cross Lanes, West Virginia. The thieves made away with $545,000 in cash that Whittaker carried around in a suitcase.[6] When asked why he would carry that much money around with him Whittaker responded "because I can". In another incident, two employees at the club, the general manager and a dancer-manager who were romantically linked, were arrested and charged with a plot to put drugs in Whittaker's drinks and then rob him.[5] On January 25, 2004, thieves once again broke into his car, this time making off with an estimated $200,000 in cash, but this was later recovered.

On September 17, 2003, Jesse Tribble, an 18-year-old on-and-off-again boyfriend of Whittaker's granddaughter Brandi Bragg, was found dead in Whittaker's home in Teays Valley, West Virginia,.[7] A coroner's report indicated that he had died from overdosing on a combination of oxycodone, methadone, meperidine, and cocaine. On December 20, 2004, Brandi Bragg, 17, was found dead on the property of a male friend after being reported missing on December 9. Her body was wrapped inside a plastic tarpaulin and dumped behind a junked van. No one was charged with a crime. Cocaine and methadone were found in her system, but the cause of death was listed as "undetermined."[5]
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Whittaker was later sued by Caesars Atlantic City casino for bouncing $1.5 million worth of checks to cover gambling losses. Whittaker also countersued, claiming that his losses were supposed to be credited due to a slot machine he developed and that they in fact owed him money.[9]

On January 11, 2007, a legal complaint against Whittaker alleged he claimed that on September 11, 2006, thieves took all of his money.[10] The thieves, 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 July 5, 2009, Ginger Whittaker Bragg, Whittaker's 42-year-old daughter and the mother of Brandi Bragg, was found dead in Daniels, West Virginia. No explanation was given but officials did not expect foul play.[11]".....