Timothy A. Connolly 3rd - Criminal Career

Criminal Career

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.

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.

A May 2001 Boston Globe expose 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."

Globe writers Shelley Murphy and Judy Rakowsky state "Timothy Connolly, a former associate of Bulger and Stephen "The Rifleman" Flemmi, said "I was down in the dirt with these guys. I know."

Physically

Tim Connolly is a former basketball player, standing six foot six, with broad shoulders and a barrel chest. He has reddish blond, fine hair and a classic Italian nose. Considered handsome, his most striking features are his steely eyes and stare. He is an accomplished boxer and is well experienced in the martial arts. The word on Connolly is “don’t mess with him unless you’re prepared to shoot him...two or three times.”

Personality

Connolly is a born leader who commands a large following in both organized crime and law enforcement circles. According to a close source, “People love him or hate him. But everyone knows enough to be afraid of him. This guy will kill you!” “Very, very sharp.” said one person who has known him for 30 years. Connolly’s IQ is rumored to be “up there with Jim Bulger’s”, which is rumored to be in the 135 to 150 range. Connolly is a known womanizer, who was known to have six or eight girlfriends at a time. Connolly was a frequent visitor to Flemmi’s brothels. “That’s one perk I did use” Connolly reportedly joked to his friends.