Notorious Gangster Whitey Bulger Hit the Jackpot

INSIDE EDITION reports on how reputed mobster Whitey Bulger could have taken a piece of a $14 million winning lottery ticket during the height of his crime spree.  

Following his extradition from Los Angeles to Boston, notorious mobster Whitey Bulger currently resides in solitary confinement. It may be hard to believe, but that man, also known as Public Enemy #1, was once a big winner in the Massachusetts state lottery.

The win happened in 1991, but to this day it remains a mystery how the former king of the Boston mob managed to hit the $14.3 million jackpot. Was it an odds-defying coincidence, or a more sinister rigged game?

In rare surveillance footage, Bulger can be seen collecting the earnings that he won in the Massachusetts state lottery.

"No one could quite believe that it happened, but there was nothing to say that it wasn't legitimately his. He held the ticket," Phyllis Karas, author of Brutal said.

At the time, lottery officials checked and rechecked their computers. They swore that everything was tamper-free.

"Everything was absolutely crystal clean," said Tom'Ohare, executive director of the Massachusetts state lottery.

The winning ticket was actually bought by a man named Michael Linskey. But Linskey had partners with whom he shared the winnings: his brother and two men from his south Boston neighborhood– Whitey Bulger and Bulger's henchman, Kevin Weeks.

The ticket was purchased at a south Boston liquor mart. And the store's owner? None other than Whitey Bulger.

When the surveillance video was taken, Bulger was collecting the first of his 20 annual installment payments of $89,000.

"When it came out, the state treasurer said it would've been less embarrassing had the state treasurer's own mother won the lottery," Karas said.

New details are also emerging about the identity of the tipster who led the FBI to Whitey Bulger and his girlfriend, Catherine Grieg, at their Santa Monica apartment.

The tipster is reportedly a woman from Iceland, of all places. She was watching CNN when she saw the now famous FBI TV commercial.

"Iceland. Seriously? Why didn't the Feds just tell us one of Santa's elves called the tip in from the North Pole?" a skeptical Boston Herald said.

Catherine Grieg is expected in court on Tuesday for a bail hearing.