Timothy A. Connolly 3rd - A History of Violence

A History of Violence

Connolly’s business acumen was well known to people in South Boston, many of whom referred to him as “one of South Boston’s new millionaires.” Yet, Connolly’s brutal, violent side made him a perfect fit for the ruthless Irish mob. He had a reputation for having a “hair trigger” and pulling a gun without hesitation. He was well known for bare knuckles bar room brawling and gun violence. Much of his criminal record has been expunged but Connolly reputedly had over twenty “assault and battery” arrests.

Connolly was the subject of Massachusetts State Police, Boston Police and DEA investigations dating all the way back to 1977. His rap sheet lists a number of violent offenses ranging from Assault, Assault and Battery, Assault and Battery with a Dangerous Weapon including Pistol Whipping, Attempted Murder, Threatening a Witness and Extortion. In addition, he was charged with dozens of lesser offenses ranging from To Wit the Sped of Beasts (Running a Gambling Operation), Selling Stolen Merchandise and Drug Dealing. In almost all cases, the charges were dropped or dismissed without a finding. Connolly was a suspect in over twenty homicides in the Boston area but has never been officially charged with murder.

Connolly was considered a serious threat both inside and outside the Irish mob because of his large following, his contacts within the La Cosa Nostra (LCN) and his ability to pull people together from other gangs to form his own gang. Connolly is half Italian on his mother's side and has strong Sicilian roots. He has several cousins and relatives who were made men in La Cosa Nostra. One cousin was a highly respected LCN "banker" who wielded considerable power and influence throughout Boston. This "cousin" mentored Tim in real estate and other business. As a result, Connolly was known to have frequent contact with Frank Salemme.

In 1990, a 45- person Organized Crime Task Force was initiated by the DEA, Massachusetts State Police, FBI, IRS, Boston Police and U.S. Customs, with the goal of putting Connolly in jail. It was believed that his business operations were "the straw that linked all of Bulger and Flemmi's activities with the LCN." (La Cosa Nostra) As a result, Connolly was under 24 hour surveillance and the subject of numerous federal wiretaps.

An August 19, 1990 front page article from the Boston Herald titled "Feds taped alleged coke boss" referenced a phone conversation between John "Red" Shea and Tim Connolly, which was recorded by the DEA. The Herald article suggested that "Red" Shea was South Boston's coke boss but Connolly was much higher up in the Winter Hill than Shea or any other drug dealers. The taped conversation was about a questionable real estate loan which Connolly secured for South Boston drug dealer, Thomas Cahill, who was part of the South Boston narcotics distribution network.

" John "Red" Shea was among 51 people charged in four separate indictments last week with working for four cocaine rings that allegedly smuggled the drug in from Florida and sold it on the city streets. In an August 30, 1989 (phone) conversation, Timothy Connolly complained to Shea that Rooney called Monarch Mortgage-which wrote (Thomas) Cahill's loan and told them his property was "overfinanced by 130 percent." Rooney told the company "It was a bogus deal and a bogus appraisal" claimed Connolly, owner of Connolly's Corner Cafe in South Boston. "he ratted on me and Tom (Cahill).

Shea offered to "go down right now and tell him to shut his (expletive) mouth or I'll shut it permanently." Connolly said "that would be the nicest thing to do."

Red Shea was found guilty of cocaine dealing and served 12 years in prison. He was released in 2002.