Newly released FBI documents provide glimpse into Whitey Bulger’s dark world

BOSTON — Nearly three years after South Boston Mob Boss James ‘Whitey’ Bulger was murdered in prison, the FBI is unlocking its ‘Bulger Files.’

The Bureau is making public 300 pages of heavily redacted documents dating back to the mid-1970s as Bulger was becoming an FBI Top Echelon Informant and consolidating his grip on Boston’s underworld. The first set of documents from 1974 reveals FBI agents discussing Bulger gang victims who were willing to wear wire tapes for the feds.


Many of the documents detail one loan sharking victim who fell far behind on his payments to Bulger. The victim told federal agents that Whitey Bulger himself, at one point, “slapped him around.” Later, the victim said he was robbed at gunpoint. The victim’s name was redacted from the file.

Bulger did not face any federal charges until the mid-1990s. That’s when he became a fugitive and was on the run until his capture 16 years later in Santa Monica, Calif.

The file also contains documents from 1977 to 1978 when the feds were building a horse race-fixing case against the Winter Hill Gang and its leader, Howie Winter. Bulger and his partner Stephen Flemmi were a part of that gang.

The documents identify Howie Winter and the Winter Hill Gang as masterminds of a scheme to fix horse races at tracks in New England and across the country.  The scheme worked through contacts in Las Vegas and involved New York Mobsters.

According to documents, jockeys were bribed to not win races, and in one case, a fast horse was given a sedative. All of this was done so that mobsters could please sure win bets, earning thousands of dollars every day.

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By the time the case went to trial, Bulger and Flemmi were Top Echelon FBI Informants. Their names were removed from federal indictments. The Horse Race Fixing Scheme was a turning point for Whitey Bulger. By the time Howie Winter was released from prison, Bulger and Flemmi were firmly in control of Boston’s underworld.

Howie Winter died in November 2020. He was 91.

It is expected the FBI will be releasing more of its Bulger files.