6. Michael Linskey
This just so happens to be one of our favorite of the 11 worst lottery winner horror stories (#11 being the obvious fave, as the only person who got hurt deserved what she got!). Not because it has a happy ending—we’ve already established all these stories end badly—but because at least one of the men tied to the story has a pretty well-known reputation. You may even recognize the South Boston mobster played by Jack Nicholson in the movie The Departed who went by the name of Whitey Bulger. Not the kinda guy you wanna mess with—that’s for sure!
You can imagine how Michael Linksey felt back in ’91 when he purchased a Mass Millions lottery ticket from a liquor store controlled by none other than Whitey Bulger, himself. When it was found out that the ticket was worth $14.3 million, it didn’t take long for Whitey to pay his new, rich friend a personal visit. Basically, Michael had one of two choices: Split the money with the feared mob boss, or die! Obviously, he split the money 50/50, but it couldn’t have been easy to just hand over millions of dollars that he had won fair and square.
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