Timothy Connolly

As a result of this huge scandal, Tim Connolly was mostly forgotten on purpose. No one at the Department of Justice wanted to talk publicly about Bulger and Flemmi. Many of the Boston FBI agents involved in the Bulger and Flemmi case retired. Federal agents were forbidden to talk publicly about the case because of liability and potential obstruction of justice. But in 2003, the federal government quietly confirmed what had been rumored. Ex-FBI Special Agent (retired), John Gamel, Connolly's FBI handler and Supervisor of Organized Crime, appeared in front of a Congressional subcommittee and stated for the record:

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

John Connolly was reportedly paid "ten grand" for this information on Tim Connolly. John Connolly is serving a ten-year, 2002 federal prison sentence, for racketeering and obstruction of justice. John Connolly was indicted in May 2008 for the murder of John Callahan, a Miami gaming executive with ties to the Winter Hill. John Connolly is currently on trial for capital murder in Miami, Florida.

A May 2001 Boston Globe exposé on "Mobster Chronicles" referenced Tim Connolly as the real deal, a true gangster, unlike "Eddie Mackenzie, a wannabe gangster who was never part of Bulger's inner circle."

In 1997, it was publicly revealed that Jim Bulger and Stevie Flemmi were secret, Top Echelon FBI informants, ratting on the New England Mafia, while conducting murder and mayhem under the FBI's nose.

Stevie Flemmi was arrested in Boston on January 5, 1995, one week prior to the release of a 37-count racketeering indictment against both he 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.

After the 1995 indictments of Flemmi and Bulger, there was widespread speculation as to who was responsible for bringing down these mob bosses.

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.

Coincident with the South Boston cocaine indictments and the Boston Herald article, Tim Connolly received reliable information that he was being "set up by Bulger and Flemmi" with the DEA. As a result, Connolly sought legal advice and counsel from private attorney Thomas Reilly. Reilly was working in private practice while running his campaign for Middlesex County District Attorney. Later, as Middlesex DA, Reilly would aggressively prosecute both Bulger and Flemmi from 1991 to 1994. It was Reilly who developed the legal strategy against Bulger and Flemmi that used bookmakers to help make the case under the Racketeer Influenced and Corrupt Organizations Act. Tom Reilly would eventually be elected Massachusetts Attorney General and served from 1999 to 2007.

In 1990, a 45-person Organized Crime Task Force was initiated by the DEA, Massachusetts State Police, FBI, Internal Revenue Service, 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.

According to court records, "in 1988 or 1989, (FBI) Agent John Connolly indirectly warned Stephen Flemmi through James Bulger that alleged extortion victim Timothy Connolly was cooperating with the FBI and would attempt to record conversations with Flemmi."

Connolly was officially "made" into the Winter Hill gang in 1984. With Flemmi's backing, he purchased a South Boston bar called the Broadway Casino and renamed it Connolly's Corner Cafe. The 3C's, as it was known in Southie, would quickly become a Winter Hill gangster front and hangout, a place from which the Irish mob ran bookmaking, loan sharking and eventually cocaine. In 1985, Connolly bought into New Boston Mortgage, a legitimate Boston area mortgage broker. Here, he developed his expertise in creating fraudulent real estate loans for Winter Hill associates. From 1985 to 1994, Connolly ran a real estate rehabilitation business with Frankie "The Flame" Fraine, a renowned arsonist, insurance scam artist and Winter Hill associate. Together they used Bulger and Flemmi's contacts to renovate condemned properties and launder cash for the mob. According to DEA sources, Connolly was believed to have been "the bank", the financing arm for the South Boston cocaine ring, lending cash to associates who actually bought and distributed the drugs. This kept Bulger and Flemmi at a safe distance from the actual drug dealing activity but not far from the profits. Connolly laundered millions of dollars in drug and gambling proceeds through a variety of real estate and off-shore banking schemes. He was a millionaire before age 30.

Tim Connolly is not to be confused with corrupt ex-FBI Special Agent John Connolly, who shares the same spelling of their last name. John Connolly is accused of accepting $235,000 in cash and gifts from Bulger and Flemmi during the 1980s in return for providing them with tips and information on ongoing police and federal investigations. In addition, ex-Agent Connolly reputedly "fingered" Winter Hill associates and gang members, who were informing on Bulger and Flemmi. A number of known informants were murdered including Richie Castucci, Brian Halloran, John Callahan and John McIntyre.

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 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.

In June 1976, Connolly joined up with Stevie Flemmi's "other gang", nicknamed "the Rox" for their hometown. He drove bales of marijuana in a U-Haul truck from south Florida to Boston under the guise of being a college student moving home. Connolly continued this practice throughout college, earning as much as $10,000 per load at the end, when they started adding cocaine to the mix. His criminal career as a drug trafficker was off and running. During college he ran a sports card gambling operation at ten colleges for Flemmi. He distributed "gaming cards" and collected cash from his dealers. By 1978 he was working as a bouncer at Flemmi's nightclubs. Then he started collecting debts for Flemmi's loan sharking business. A part-time job at a South Boston jewelry store put him in touch with Flemmi's partner, Jim Bulger, beginning in 1978.

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.

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.

Timothy A. Connolly III (born May 27, 1958), aka "Timmy Connolly" and "TC", is 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.