Timothy A. Connolly III (May 27, 1958 - July 21, 2020), aka "Timmy Connolly" and "TC", was an American former South Boston bar owner and mortgage broker, who wore a wire inside the infamous Winter Hill Gang and helped the federal government indict their two leaders, James "Whitey" Bulger and Stephen Flemmi ("The Rifleman"). The public was led to believe that Tim Connolly was merely a businessman and an innocent victim of one of Jim Bulger's many extortions. But in truth, Tim Connolly was secretly a "made member" of the Winter Hill gang and a high ranking lieutenant in this Bulger crime family.
Early life
Connolly was born and raised in Roxbury, Massachusetts, US, the hometown of Stevie Flemmi. He is the youngest of three children. His father is Irish-American and his mother is Italian (Sicilian). Like Flemmi and several other members of the Winter Hill, Connolly grew up in the Orchard Park projects, one of the first low-income housing projects in Boston. At age 12, Connolly's family moved over the city line into a working class section of Milton, a wealthy suburb of Boston. At age 15, Tim Connolly befriended a high school classmate, Billy Hussey, Stevie Flemmi's biological son. Connolly met "Stevie" and their relationship grew from there. Flemmi would ultimately become Connolly's mentor and boss for the next three decades.
Connolly graduated from Milton High School in 1976, where he was captain of the basketball team, earning all star honors. He attended Bridgeton Academy, Maine for a post graduate year. In September 1977 Connolly entered Boston College on a partial basketball scholarship. He quit before the season started. Connolly graduated from BC in 1981.
The Winter Hill Gang
The Winter Hill gang, aka "The Irish Mob", is an Irish American crime family (with Italian American associates) operating in the region of Boston, Massachusetts, dating back to the early 1960s. The Winter Hill gang was considered one of the most ruthless and violent white gangs in America. It operated for thirty years; running a portion of Boston's gambling rackets, drugs and did "brutal hits" for the Patriarca crime family (the New England Mafia), until its two leaders were indicted in January 1995.
Tim Connolly was an early protege of Stevie Flemmi, a renowned homicidal maniac of Italian descent. Beginning as a teenager in the mid-1970s, Connolly went to work for Flemmi, collecting gambling receipts and moving marijuana. Over the next decade, Connolly worked his way up from the bottom to the top spot below Bulger and Flemmi. From 1984 through 1994, Connolly operated several legitimate and illegitimate businesses which fronted for the Irish mob. In addition, Connolly ran his own criminal crew, which offered protection, loan sharking, gambling and drug distribution. Connolly was a close associate of both Flemmi and Bulger, having been seen with them on hundreds of occasions by Drug Enforcement Administration and Federal Bureau of Investigation (FBI) agents performing surveillance. Connolly was one of only two lieutenants who met daily with Bulger and Flemmi. The other was Bulger's driver and bodyguard, Kevin Weeks.
Stevie Flemmi was arrested in Boston on January 5, 1995, one week prior to the release of a 37-count racketeering indictment against both him and Bulger. Flemmi has not been released from prison since. He is serving consecutive life sentences in a witness protection prison for his admitted participation in the murders of 10 people including two women. It is rumored that Flemmi committed over 50 murders himself and is responsible for the death of over 100 people, mostly career criminals.
Jim Bulger was tipped off by corrupt FBI agent John Connolly before the indictments came down and fled Boston. Since the Racketeer Influenced and Corrupt Organizations Act indictments, Jim Bulger has also been charged with twenty murders.
Tim Connolly was shot in Boston's Chinatown neighborhood in an apparent assassination attempt in November 1994. Two weeks later, entering the Federal Courthouse on crutches, he provided crucial testimony to a grand jury that resulted in the racketeering indictments against Bulger and Flemmi. Connolly entered the Witness Protection Program in December 1994 but is rumored to have been "kicked out" within two years. He is believed to be "banned from Boston" as part of his deal with the United States Department of Justice. He has not been seen in Boston in over a decade. Unlike Winter Hill Associates Kevin Weeks, John "Red" Shea, Eddie Mackenzie and Pat Nee, Connolly has turned down several book deals and offers to be interviewed. He is rumored to be completing his life inside the Irish mob.