Claim: Judge Denise Casper sentenced Whitey Bulger.

James Joseph `` Whitey '' Bulger , Jr. -LRB- -LSB- ˈbʌldʒə -RSB- born September 3 , 1929 -RRB- is an Irish-American former organized crime boss of the Winter Hill Gang in Boston . Federal prosecutors indicted Bulger for 19 murders based on grand jury testimony from Kevin Weeks and other former associates . Bulger is the brother of William `` Billy '' Bulger , former President of the Massachusetts Senate .   According to the FBI , Bulger served as an informant for the Federal Bureau of Investigation -LRB- FBI -RRB- beginning in 1975 . Bulger denies this . However , as a result , the Bureau largely ignored his organization in exchange for information about the inner workings of the rival Italian-American Patriarca crime family . Beginning in 1997 , the New England media exposed criminal actions by federal , state , and local law enforcement officials tied to Bulger . For the FBI especially , this caused great embarrassment . Bulger fled Boston and went into hiding on December 23 , 1994 , after being tipped off by his former FBI handler , John Connolly , about a pending indictment under the Racketeer Influenced and Corrupt Organizations Act -LRB- RICO -RRB- . For 16 years , he remained at large . For 12 of those years , Bulger was on the FBI Ten Most Wanted Fugitives list .   On June 22 , 2011 , Bulger was arrested outside an apartment in Santa Monica , California . Arrested with him was his long-time girlfriend Catherine Greig . Bulger was 81 years old at the time . Soon after , Bulger and Greig were extradited to Massachusetts and taken under heavy guard to John Joseph Moakley United States Courthouse on Boston Harbor , which had to be partially closed for their arrival . Greig pleaded guilty to conspiracy to harboring a fugitive , identity fraud , and conspiracy to commit identity fraud and was sentenced in June 2012 to eight years in prison . Bulger did not seek bail and remained in custody at the Plymouth County House of Correction in Plymouth , Massachusetts . On November 5 , 2012 , Bulger was taken to a hospital from his Plymouth prison cell after complaining about chest pains .   On June 12 , 2013 , Bulger went on trial for 32 counts of racketeering , money laundering , extortion , and weapons charges , including complicity in 19 murders . On August 12 , 2013 , he was found guilty on 31 counts , including both racketeering charges , and was found to have been involved in 11 murders . On November 14 , 2013 , Bulger was sentenced to two consecutive life terms plus five years for his crimes by U.S. District Judge Denise Casper . Bulger is now inmate number 02182-748 currently incarcerated for life at the United States Penitentiary Coleman II in Sumterville , Florida .   Bulger was also possibly involved in the murder of an unidentified woman -- the `` Lady of the Dunes '' -- in Provincetown , Massachusetts , in 1974 . After one of many facial reconstructions was released , it was reported that he had been seen in the city with a woman who matched her description .   Bulger 's assets were auctioned off on June 25 , 2016 , raising $ 109,000 for his victims . Among the items on auction were a rat-shaped pencil holder that went for $ 3,600 , a 1992 excise tax bill from the City of Boston -LRB- $ 160 -RRB- , and his lock-picking kit -LRB- $ 125 , as part of a lot including 95 mini flashlights , a pocket knife and a Leatherman tool -RRB- .