The FBI Agent Who Helped Whitey Bulger Escape: The Disgraced Legacy of John Connolly
South Boston native turned FBI agent John Connolly went from chasing gangsters to becoming one
Background
Just a few days before Christmas in 1994, notorious South Boston crime boss James “Whitey” Bulger fled Boston with his longtime girlfriend Catherine Greig.
He was fleeing the place where he had risen up the ranks of the city’s underworld, essentially becoming South Boston’s boogie man.
Although his departure had come suddenly and unexpectedly, in truth, Bulger had been preparing for this for years. He had squirreled away millions of dollars from his decades of criminal activities and deposited it in various bank accounts in the United States as well as overseas. He had amassed a collection of false identifications as well as various disguises.
Bulger was a shrewd criminal who knew that someday, his only chance at freedom would be life as a fugitive. He had meticulously planned for this inevitability, which allowed Bulger and Greig to successfully evade capture for more than 16 years.
However, none of that would have been possible unless Bulger had been tipped off about the upcoming indictments of him and other members of his organization.
There was a reason why it seemed that for years, Bulger was always a step ahead of law enforcement.
What few knew at the time was that Bulger had an FBI agent feeding him information, protecting him, and running interference with other law enforcement agencies.
Neighborhood Ties
John Connolly was nine years old when he first met James Bulger. The Connollys and Bulgers were neighbors in the Old Harbor Housing Project in South Boston.
Bulger who was eleven years older than Connolly, already had a reputation as a neighborhood tough guy who was not to be messed with. One day, Connolly was being bullied by a group of older kids. When Whitey saw what was going on, he stepped in and chased the kids away.
Bulger then bought the awestruck Connolly an ice cream.
South Boston, a historically Irish area of the city, was known as a place where neighbors looked out for one another. Many residents were extremely distrustful of outsiders, and most issues were resolved without involving law enforcement.
Over the ensuing decades, both Connolly and Bulger embarked on different paths. Whitey, already a well-known hoodlum, would pay his dues and climb the ranks of the Boston underworld. At one point, even serving a stint in the notoriously harsh Alcatraz prison for a series of bank robberies.
Bulger was able to reduce his sentence by agreeing to participate in an experiment to study the effects of LSD as a possible weapon for mind control. Although this allowed Bulger to cut his prison sentence short, he would later admit that he suffered long-lasting effects from the experiments.
Meanwhile, John Connolly received encouragement, ironically enough, from Whitey’s younger brother William Bulger, who was six years older than Connolly. William told the young Connolly that getting an education and going to college was the path to success.
William Bulger knew of what he spoke. He graduated from Boston College and later went to law school. He became the longest-serving President of the Massachusetts Senate and later went on to be president of the University of Massachusetts.
Following William Bulger’s advice, Connolly attended and graduated Boston College, and like William, went on to law school. He later earned a graduate degree from Harvard University.
Joining the FBI
In 1968, Connolly joined the FBI and served in several field offices, including Baltimore, San Francisco, and New York City. In 1973, he was assigned to his hometown of Boston.
During this time, the FBI was particularly interested in disrupting the activities of the mafia in Boston and New England. Connolly was also instrumental in helping develop the FBI’s Top Echelon Criminal Informants Program.
The aim of the program was to develop informants who were involved in criminal activities themselves and had information that could help the feds build cases against their desired targets.
Recruiting Whitey Bulger
During the early 1970s, Whitey Bulger, then a member of the mostly Irish Winter Hill Gang, was feuding with the New England mafia led by Raymond Patriarca. These disputes, which involved rackets and turf within Boston, played right into the hands of the FBI.
Unbeknownst to those around him, Bulger’s partner in crime, Stephen “The Rifleman” Flemmi, had been an FBI informant since 1965. The FBI had tried unsuccessfully to recruit Bulger in 1971, but he had refused.
However, Connolly was eventually able to bring Bulger into the fold. Several factors likely played into Connolly’s favor. One being that Bulger remembered him from the old neighborhood, and another being that the FBI would simultaneously go after Bulger’s rivals within the mafia while shielding Bulger and his men from law enforcement scrutiny.
Whitey was given his own file, which Connolly would sometimes pad in order to justify Bulger’s worth to the Bureau. Attributing information obtained from other sources to Bulger made him appear to be a more valuable asset than he really was.
In 1977, FBI Supervisor John Morris was placed as head of the Bureau’s Organized Crime Squad in the Boston field office. However, Morris himself would prove to be nearly as corrupt as Connolly and only escaped prison by testifying against Connolly.
The fact that the FBI was so intent on going after Italian organized crime was a major benefit to Bulger. He and his crew were involved in many of the same activities as the mafia such as bookmaking, gambling, extortion, and murder. However, the seemingly less organized Irish gangs were seen as a lesser priority.
Crossing Over
As the relationship with Bulger deepened, the gangster seemed to have an effect on the agent. Other agents began to notice Connolly’s stylish clothes and well-manicured hair. Bulger began referring to Connolly as “Zip” a reference to the fact that they both grew up in the same zip code.
Connolly was also showing a lot of cash for a federal employee. During the 1980s, Connolly made several high-end purchases including a boat, multiple condos, and houses.
An FBI employee who worked under Connolly recalled opening his desk drawer one time and finding ten uncashed paychecks.
It seems Connolly had been seduced by the lifestyle that Bulger’s dirty money brought. As shameful as this corruption was, it would later come out that Connolly’s leaks to Bulger directly led to at least two murders.
Revelations, Trial, and Sentencing
While Whitey Bulger was able to flee Boston in late 1994 ahead of impending indictments, other members of his organization were arrested and stood trial on numerous racketeering charges.
During the court proceedings, many shocking revelations emerged, most notably, the unholy relationship between Connolly and, to a lesser extent, John Morris and the Bulger organization.
Stephen Flemmi testified about numerous bribes and other gifts they had given to Connolly in appreciation of his service to the gang. Most damning of all for Connolly was the revelation that information he fed Bulger led to two men being murdered.
The 1981 murder of Oklahoma businessman Roger Wheeler and the 1982 murder of John Callahan. At the time of their deaths, both men were being investigated regarding their dealings with Bulger.
As a direct result of Connolly’s information, both men were killed by Bulger’s hitmen.
In 2008, Connolly was convicted of second-degree murder for the death of John Callahan in Florida. Though the minimum sentence for the crime was 30 years, the judge sentenced Connolly to 40 years, citing that an FBI agent should be held to a higher standard.
He also received a 10-year federal sentence for the conspiracy charges, which he served in North Carolina before being sent to Florida to serve his 40-year sentence.
Update
In 2021, John Connolly was granted medical release from prison after his attorney claimed that he was gravely ill and only had about a year to live. However, as time continues to pass and reports say Connolly’s condition may be improving, prosecutors are discussing sending him back to prison.
Senior trial counsel Michael Von Zamft said, “Prosecutors only agreed to Connolly’s release because they believed he was terminally ill. And since he is not terminal, he should return to prison.”
Despite the fact his crimes occurred while employed as an FBI agent, Connolly continues to receive pension benefits as a former federal agent.
Sources:
Nealon, Patricia. “FBI was aware of crimes by informants, ex-supervisor testifies.” The Boston Globe, 12 June 1998, p. 36, https://www.newspapers.com/image/441528651/?match=1&terms=john%20connolly
Neavling, Steve. “Disgraced Former FBI Agent John Connolly to Remain Free of Prison Despite Improving Health.” Tickle The Wire, https://ticklethewire.com/disgraced-former-fbi-agent-john-connolly-to-remain-free-of-prison-despite-improving-health/
Patmore, Neil. “The Secret Life Of John Connolly, The Boston FBI Agent Who Partnered With Infamous Mob Boss Whitey Bulger.” all that is interesting, 29 March 2023, https://allthatsinteresting.com/john-connolly