9. Michael Linskey
In 1991 Michael Linskey bought a $14 million winning lottery ticket from a South Boston corner store. This store just happened to be owned by feared Boston mobster Whitey Bulger. The story goes that Bulger bullied Linskey into sharing his winnings since the winning ticket was bought at his store. Linskey took half of the winnings and the other half was split between Bulger, Kevin Weeks, and Linskey’s brother Patrick. The four men actually signed a notarized statement informing the world that they all agreed to this financial arrangement. It was proposed four years later that Bulger bought into the winnings with laundered money while the mobster was being investigated by U. S. Attorney Donald K. Stern. It can only be imagined how scary it is to be shaken down by a legendary Boston mobster, probably scary enough to forget how fun it is to have won such a huge sum of money from the lottery.
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