Timothy A. Connolly 3rd
Encyclopedia
Timothy A. Connolly 3rd (born May 27, 1958), aka "Timmy Connolly" and "TC" is a 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 "The Rifleman" Flemmi. 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 Boston crime family.
crime family
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 shark
ing, gambling and drug distribution. Connolly was a close associate of both Flemmi and Bulger, having been seen with them on hundreds of occasions by DEA
and 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 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.
Jim Bulger was tipped off by corrupt FBI agent John Connolly
before the indictments came down and fled Boston. Since the RICO
indictments, Jim Bulger has also been charged with twenty murders. He has been a federal fugitive for thirteen years. He is the FBI's Most Wanted
American fugitive and overall, second only to Osama bin Laden
on the FBI's Ten Most Wanted List. There is a two million dollar reward for information leading to the arrest of James "Whitey" Bulger.
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.
A front page Boston Globe article stated:
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.
The ensuing FBI scandal, involving Bulger and Flemmi, has been called "one of the greatest failures in the history of federal law enforcement" and quite possibly "the biggest scandal in FBI history."
"Memos show that for more than twenty years, FBI headquarters in Washington D.C. knew that Boston agents were using hit men and mob leaders as informants and shielding them from prosecution for serious crimes, including murder."
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:
, USA, 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.
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 arson
ist, 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.
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.
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.
who developed the legal strategy against Bulger and Flemmi that used bookmakers to help make the case under the RICO statutes. Tom Reilly would eventually be elected Massachusetts Attorney General
and served from 1999 to 2007.
After hearing Connolly's story, Reilly put him together with the U.S. Attorney for Massachusetts, A. John Pappalardo. After some legal wrangling and a grant of immunity, Connolly agreed to become a Top Echelon informant on Bulger and Flemmi. His Top Secret Operation was dubbed "Close Shave" or "Clean Shave" by his FBI handlers. They figured that Bulger would slit Connolly's throat if he ever found out he was wearing a wire and recording conversations. Connolly reportedly wore a wire for four years, gathering evidence, while the government's case was slowed by ex-FBI Agent John Connolly and corruption within the Boston FBI office.
, 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.
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." .
John Connolly was reportedly paid "ten grand" for this information on Tim Connolly.
John Connolly is currently 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
.
In reality, it was Bulger and Flemmi who were "rats". They were setting up Tim Connolly with the DEA because they thought he was a major threat. They were willing to trade him (along with 50 associates who pled guilty to narcotics distribution) in return for a four year pass with the feds.
When the indictments came down against the Winter Hill, Connolly refused to testify against anyone other than Bulger and Flemmi. He put his life on the line for four years inside the Irish mob while the feds fumbled their case.
One ex-FBI agent who requested anonymity said this abou Tim Connolly: "TC outfoxed the foxes. He got to them before they got to him. That takes balls and smarts."
Winter Hill Gang
The Winter Hill Gang is a structured confederation of Boston, Massachusetts-area organized crime figures, predominantly Irish-American with a small Italian-American faction. It derives its name from the Winter Hill neighborhood of Somerville, Massachusetts north of Boston. Its members have...
and helped the federal government indict their two leaders, James "Whitey" Bulger and Stephen "The Rifleman" Flemmi. 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 Boston crime family.
The Winter Hill Gang
The Winter Hill gang, aka "The Irish Mob", is an Irish AmericanIrish American
Irish Americans are citizens of the United States who can trace their ancestry to Ireland. A total of 36,278,332 Americans—estimated at 11.9% of the total population—reported Irish ancestry in the 2008 American Community Survey conducted by the U.S. Census Bureau...
crime family
Crime family
A crime family is a term used to describe a unit of an organized crime syndicate, often operating within a specific geographic territory. The term is used almost exclusively to refer to units of the Mafia, both in Sicily and in the United States, although it is occasionally used to refer to other...
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
Patriarca crime family
The Patriarca crime family, also known as the New England crime family and the Providence crime family, is an Italian-American organized crime syndicate based in New England, specifically Providence, Rhode Island and Boston, Massachusetts, and is part of the Italian-American Mafia or "La Cosa Nostra"...
(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 shark
Loan shark
A loan shark is a person or body that offers unsecured loans at illegally high interest rates to individuals, often enforcing repayment by blackmail or threats of violence....
ing, gambling and drug distribution. Connolly was a close associate of both Flemmi and Bulger, having been seen with them on hundreds of occasions by DEA
DEA
DEA is the commonly used acronym for the Drug Enforcement Administration, a United States law enforcement agency.DEA or Dea may also refer to:- Organizations :* DEA , UK development education charity...
and 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
Kevin Weeks
Kevin Weeks is a former mobster of Irish-American descent and a longtime friend and confidant to James J. Bulger, the infamous boss of the Winter Hill Gang, a crime family based out of the Winter Hill neighborhood in Somerville, Massachusetts.After his arrest and imprisonment in 1999, he became a...
.
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
Witness protection
Witness protection is protection of a threatened witness or any person involved in the justice system, including defendants and other clients, before, during and after a trial, usually by police...
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
John Connolly (FBI)
John J. Connolly, Jr. is a former FBI agent, who was convicted of racketeering and obstruction of justice convictions stemming from his relationship with James J. "Whitey" Bulger, Steve Flemmi, and the Winter Hill Gang...
before the indictments came down and fled Boston. Since the RICO
RICO
-Music:*Rico , a 2000 album by Matt Bianco*"Rico" , a 1998 song the Matthew Good Band from the album Underdogs*Rico International, a manufacturer of reeds, mouthpieces, and woodwind accessories...
indictments, Jim Bulger has also been charged with twenty murders. He has been a federal fugitive for thirteen years. He is the FBI's Most Wanted
Most Wanted
*Lists used by law enforcement agencies to alert the public, such as:**FBI Ten Most Wanted Fugitives**FBI Most Wanted Terrorists**United States Secret Service Most Wanted Fugitives**U.S...
American fugitive and overall, second only to Osama bin Laden
Osama bin Laden
Osama bin Mohammed bin Awad bin Laden was the founder of the militant Islamist organization Al-Qaeda, the jihadist organization responsible for the September 11 attacks on the United States and numerous other mass-casualty attacks against civilian and military targets...
on the FBI's Ten Most Wanted List. There is a two million dollar reward for information leading to the arrest of James "Whitey" Bulger.
Tim Connolly was shot in Boston's Chinatown
Chinatown
A Chinatown is an ethnic enclave of overseas Chinese people, although it is often generalized to include various Southeast Asian people. Chinatowns exist throughout the world, including East Asia, Southeast Asia, the Americas, Australasia, and Europe. Binondo's Chinatown located in Manila,...
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
United States Department of Justice
The United States Department of Justice , is the United States federal executive department responsible for the enforcement of the law and administration of justice, equivalent to the justice or interior ministries of other countries.The Department is led by the Attorney General, who is nominated...
. 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.
Who brought down Bulger and Flemmi?
After the 1995 indictments of Flemmi and Bulger, there was widespread speculation as to who was responsible for bringing down these mob bosses.A front page Boston Globe article stated:
- Timothy A. Connolly 3d, a one time proprietor of a South Boston bar frequented by ne'er-do-wells, emerged as a crucial witness against Bulger, accusing Bulger of menacing him with a knife while extorting money.
- Apparently (Connolly) worked as an informant for the FBI for several years before joining Chico Krantz and other bookie, Jimmy Katz, in the Witness Protection Program. In a deal brokered by then-U.S. Attorney John Pappalardo in 1991, Timothy A. Connolly 3d, (who owned the Corner Cafe.) became an FBI informant when he could not make his alleged extortion payments to Kevin Weeks, a close Bulger associate.
- Connolly, who worked for a Waltham mortgage company, was pushed into investigator's arms, according to interviews and court records, simply because he took too long to help a drug trafficker in South Boston pay off a $40,000 debt to Bulger.
- Connolly was summoned to the back room of the Rotary Variety store in South Boston in July 1989. And it was there, according to a court affidavit, that Bulger threw caution to the wind and did his own dirty work, menacing Connolly by drawing a long knife from a sheath on his leg, punctuating a tirade by stabbing nearby boxes and waving the blade around Connolly's face. Connolly was purportedly "fined" $50,000 that was to be split between Bulger and Weeks. Two years later, Connolly went to the U.S. Attorney's office and is now a cooperating witness who is believed to have worn a body wire around town last year."
- For all intents and purposes, Whitey Bulger was untouchable until an incident that allegedly occurred one night in 1989. Late in the evening, Whitey allegedly arrived at his "office" behind the liquor store, to take care of some unfinished business. Reportedly, Whitey's associate, Stephen "The Rifleman" Flemmi, stood waiting inside. Their guest of honor was a local tavern owner named Tim Connolly, whom Whitey had allegedly targeted for extortion. Two days later, after Whitey had allegedly threatened Tim Connolly, Tim did the only thing he felt he could do. He returned to the liquor store with $25,000 cash. But Connolly also did something else. He went to the FBI. They, in turn, began building a case against the so-called "Don of South Boston." Connolly provided authorities with the evidence needed to build up a federal racketeering case against Bulger.
- "Timothy Connolly...had a simple story of extortion to tell about Bulger putting a knife to his throat for money. But the U.S. Attorney's Office tried to turn Tim Connolly's solid single into a home run. They constructed an elaborate plan to infiltrate Bulger's financial operation...U.S. Attorney A. John Pappalardo decided to use Tim Connolly to get into Bulger's finances. He turned Tim Connolly over to two handpicked FBI agents who had no ties to John Connolly. They wired the mortgage broker as a way to get an inside look at Bulger's money laundering."
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.
The ensuing FBI scandal, involving Bulger and Flemmi, has been called "one of the greatest failures in the history of federal law enforcement" and quite possibly "the biggest scandal in FBI history."
"Memos show that for more than twenty years, FBI headquarters in Washington D.C. knew that Boston agents were using hit men and mob leaders as informants and shielding them from prosecution for serious crimes, including murder."
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:
- "the case against (James "Whitey" Bulger) started in July 1990, when Tim Connolly was referred to the FBI by Tom Reilly, a private attorney. Connolly was a mortgage broker who prepared fraudulent mortgage schemes for associates of James "Whitey" Bulger. Connolly informed the FBI that James "Whitey" Bulger had personally extorted $50,000 from him and that he had been "shook down" in the backroom of a liquor store with a knife to his chest."
Early life
Connolly was born and raised in Roxbury, MassachusettsRoxbury, Massachusetts
Roxbury is a dissolved municipality and current neighborhood of Boston, Massachusetts, United States. It was one of the first towns founded in the Massachusetts Bay Colony in 1630, and became a city in 1846 until annexed to Boston on January 5, 1868...
, USA, the hometown of Stevie Flemmi. He is the youngest of three children. His father is Irish-American and his mother is Italian (Sicilian
Sicilian
Sicily is an autonomous Italian island. The adjectival form Sicilian can also refer to:* Sicilian language* Sicilian Baroque, baroque architecture in 17th & 18th centuries on Sicily...
). Like Flemmi and several other members of the Winter Hill, Connolly grew up in the Orchard Park projects
Public housing in the United States
Public housing in the United States has been administered by federal, state and local agencies to provide subsidized assistance for low-income and people living in poverty. Now increasingly provided in a variety of settings and formats, originally public housing in the U.S...
, 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
Maine
Maine is a state in the New England region of the northeastern United States, bordered by the Atlantic Ocean to the east and south, New Hampshire to the west, and the Canadian provinces of Quebec to the northwest and New Brunswick to the northeast. Maine is both the northernmost and easternmost...
for a post graduate year. In September 1977 Connolly entered Boston College
Boston College
Boston College is a private Jesuit research university located in the village of Chestnut Hill, Massachusetts, USA. The main campus is bisected by the border between the cities of Boston and Newton. It has 9,200 full-time undergraduates and 4,000 graduate students. Its name reflects its early...
on a partial basketball scholarship. He quit before the season started. Connolly graduated from BC in 1981.
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-HaulU-Haul
U-Haul International, Inc. is an American equipment rental company, based in Phoenix, Arizona, that has been in operation since 1945. The company was founded by Leonard Shoen U-Haul International, Inc. is an American equipment rental company, based in Phoenix, Arizona, that has been in operation...
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 arson
Arson
Arson is the crime of intentionally or maliciously setting fire to structures or wildland areas. It may be distinguished from other causes such as spontaneous combustion and natural wildfires...
ist, insurance scam artist and Winter Hill associate. Together they used Bulger and Flemmi's contacts to renovate condemned properties and launder
Money laundering
Money laundering is the process of disguising illegal sources of money so that it looks like it came from legal sources. The methods by which money may be laundered are varied and can range in sophistication. Many regulatory and governmental authorities quote estimates each year for the amount...
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.
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
Massachusetts State Police
The Massachusetts State Police is an agency of the Commonwealth of Massachusetts' Executive Office of Public Safety and Security responsible for criminal law enforcement and traffic vehicle regulation across the state...
, 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
In law, assault is a crime causing a victim to fear violence. The term is often confused with battery, which involves physical contact. The specific meaning of assault varies between countries, but can refer to an act that causes another to apprehend immediate and personal violence, or in the more...
, Assault and Battery, Assault and Battery with a Dangerous Weapon including Pistol Whipping, Attempted Murder, Threatening a Witness and Extortion
Extortion
Extortion is a criminal offence which occurs when a person unlawfully obtains either money, property or services from a person, entity, or institution, through coercion. Refraining from doing harm is sometimes euphemistically called protection. Extortion is commonly practiced by organized crime...
. 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
Frank Salemme
Francis P. Salemme [Salemone], also known as "Cadillac Frank" and "Julian Daniel Selig" , is a Boston, Massachusetts mobster who became a hitman and eventually the boss of the Patriarca crime family of New England before turning government witness.-Early years:In 1957, while in prison, Salemme...
.
In 1990, a 45- person Organized Crime Task Force was initiated by the DEA, Massachusetts State Police
Massachusetts State Police
The Massachusetts State Police is an agency of the Commonwealth of Massachusetts' Executive Office of Public Safety and Security responsible for criminal law enforcement and traffic vehicle regulation across the state...
, 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
Boston Herald
The Boston Herald is a daily newspaper that serves Boston, Massachusetts, United States, and its surrounding area. It was started in 1846 and is one of the oldest daily newspapers in the United States...
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.
Top Echelon FBI Informant
Coincident with the South Boston cocaine indictments and the Boston Herald article, Tim Connolly received reliable information that he was being "setup by Bulger and Flemmi" with the DEA. As a result, Tim Connolly sought legal advice and counsel from private attorney Tom 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 1991-1994. It was Tom ReillyThomas Reilly
Thomas F. Reilly is an American attorney and politician who served as the 45th Massachusetts Attorney General. He was born in Springfield, Massachusetts to Irish immigrant parents....
who developed the legal strategy against Bulger and Flemmi that used bookmakers to help make the case under the RICO statutes. Tom Reilly would eventually be elected Massachusetts Attorney General
Massachusetts Attorney General
The Massachusetts Attorney General is an elected executive officer of the Massachusetts Government. The office of Attorney-General was abolished in 1843 and re-established in 1849. The current Attorney General is Martha Coakley....
and served from 1999 to 2007.
After hearing Connolly's story, Reilly put him together with the U.S. Attorney for Massachusetts, A. John Pappalardo. After some legal wrangling and a grant of immunity, Connolly agreed to become a Top Echelon informant on Bulger and Flemmi. His Top Secret Operation was dubbed "Close Shave" or "Clean Shave" by his FBI handlers. They figured that Bulger would slit Connolly's throat if he ever found out he was wearing a wire and recording conversations. Connolly reportedly wore a wire for four years, gathering evidence, while the government's case was slowed by ex-FBI Agent John Connolly and corruption within the Boston FBI office.
The "Other Connolly"
Tim Connolly is not to be confused with corrupt ex-FBI Special Agent John ConnollyJohn Connolly (FBI)
John J. Connolly, Jr. is a former FBI agent, who was convicted of racketeering and obstruction of justice convictions stemming from his relationship with James J. "Whitey" Bulger, Steve Flemmi, and the Winter Hill Gang...
, 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.
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." .
John Connolly was reportedly paid "ten grand" for this information on Tim Connolly.
John Connolly is currently serving a ten year, 2002 federal prison sentence, for racketeering and obstruction of justice
Obstruction of justice
The crime of obstruction of justice, in United States jurisdictions, refers to the crime of interfering with the work of police, investigators, regulatory agencies, prosecutors, or other officials...
. 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
Miami, Florida
Miami is a city located on the Atlantic coast in southeastern Florida and the county seat of Miami-Dade County, the most populous county in Florida and the eighth-most populous county in the United States with a population of 2,500,625...
.
Tim Connolly Didn't Rat
In the book "Paddy Whacked: The Untold Story of the Irish-American Gangster" the author mistakenly accuses Timothy Connolly of being "a rat."- " The federal prosecutors had put together a big case against the South Boston mob and it included a number of rats, most notably Timothy Connolly (no relation to John) who was the proprietor of a South Boston tavern that had been the hub of Bulger's cocaine operation. Connolly also had information that linked Bulger and Flemmi to at least two murders, which was enough to put the mobsters away for the rest of their natural born lives."
In reality, it was Bulger and Flemmi who were "rats". They were setting up Tim Connolly with the DEA because they thought he was a major threat. They were willing to trade him (along with 50 associates who pled guilty to narcotics distribution) in return for a four year pass with the feds.
When the indictments came down against the Winter Hill, Connolly refused to testify against anyone other than Bulger and Flemmi. He put his life on the line for four years inside the Irish mob while the feds fumbled their case.
One ex-FBI agent who requested anonymity said this abou Tim Connolly: "TC outfoxed the foxes. He got to them before they got to him. That takes balls and smarts."