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September 3, 1929 - Whitey Bulger

His decades-long reign over South Boston's criminal underworld was made possible not just by violence, but by a calculated arrangement with the FBI that shielded the Winter Hill Gang from federal scrutiny while rivals were dismantled around them. The corruption that sustained him ran deep enough to embarrass multiple government agencies when it finally unraveled. He spent sixteen years as a fugitive before his 2011 capture, by which point his case had become as much a story about institutional failure as about organized crime.

From Wikipedia

Whitey Bulger

James Joseph "Whitey" Bulger Jr. ( ; September 3, 1929 – October 30, 2018) was an American organized crime boss who led the Winter Hill Gang, an Irish mob group based in the Winter Hill neighborhood of Somerville, Massachusetts, northwest of Boston. On December 23, 1994, Bulger went into hiding after his former FBI handler, John Connolly, tipped him off about a pending RICO indictment against him. He remained at large for sixteen years. After his 2011 capture, federal prosecutors tried Bulger for nineteen murders based on grand jury testimony from Kevin Weeks and other former criminal associates.

Although he adamantly denied it, the FBI stated that Bulger had served as an informant for several years starting in 1975, providing information about the inner workings of the Patriarca crime family, his Italian-American Mafia rivals based in Boston and Providence, Rhode Island. In return, Connolly, as Bulger's FBI handler, ensured that the Winter Hill Gang was effectively ignored. Beginning in 1997, press reports exposed various instances of criminal misconduct by federal, state and local officials with ties to Bulger, causing embarrassment to several government agencies, especially the FBI.

Five years after his flight from the Boston area, Bulger was added to the FBI's Ten Most Wanted Fugitives list; he was considered the most wanted person on the list behind Osama bin Laden. Another twelve years passed before he was apprehended along with his longtime girlfriend, Catherine Greig, outside an apartment complex in Santa Monica, California.

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