AlthoughBlack Masscenters on Boston-based mobster James “Whitey” Bulger (Johnny Depp), the biographical crime drama has viewers wonderingwhat, exactly, happened to FBI agent John Connolly (Joel Edgerton) in the wake of his partnership with Bulger. Based on the bookBlack Mass: The True Story of an Unholy Alliance Between the FBI and the Irish Mob,Depp’s controversial crime moviedelves into what unfolded in Boston during the mid-1970s. Bulger, who helmed the Irish Mob’s Winter Hill Gang, was the most powerful organized crime leader in South Boston, even though his family’s roots caught Connolly’s attention.
Growing up in the tight-knit South Boston community, the FBI agent had been a friend of both Whitey and his brother, another member ofBlack Mass' cast of characters. In a strange twist of fate, Whitey becomes an informant for Connolly, who hopes to infiltrate a rival Italian crime syndicate — the Angiulo Brothers. Sincethe Angiulos pose a real threat to Bulger’s power, the Southie mobster decides that becoming a rat for the FBI is his best path forward. However, Whitey Bulger cleverly exploits Connolly’s protection, allowing the Winter Hill Gang to continue its criminal operations relatively unscathed.
John Connolly’s Racketeering Offenses Explained
In Black Mass, Connolly’s Federal Charges Included Racketeering
Ultimately, John Connolly was saddled with racketeering offenses, among many other charges. Even after Bulger helped Connolly and his FBI colleagues arrest the Angiulo Brothers, Connolly was seduced by the mobster’s charm, refusing to see the dangerous criminal for who he really was beyond the informant title. Connolly’s FBI colleague, Brian Halloran (Peter Sarsgaard), reported everything to his superiors, but, as seen inBlack Mass' ending, the move resulted in Halloran’s death. Eventually,the tenuous — and increasingly corrupt — nature of Whitey and Connolly’s relationship landed on the front page ofThe Boston Globe, prompting Bulger to flee Boston.
As of September 2024,Black Massis streaming on Netflix.
On a federal level, Connolly was charged with racketeering for his involvement with Whitey Bulger and the Irish Mob. Generally speaking, racketeering is a type of organized crime that hinges on the creation of an unlawful scheme that’s disguised as a legitimate business, allowing those involved to turn a profit through illegal means. As seen inJohnny Depp’s mob movie, Connolly was so embedded in Whitey Bulger’s fold, and willing to accept money and gifts, it’s not surprising that he received racketeering charges. In 2002,Connolly was officially convicted and sentenced to a decade in federal prison(viaThe Guardian).
John Connolly Was Sentenced To 40 Years In Prison In 2008
Second-Degree Murder Charges Landed Connolly A Stint In Florida Prison
In addition to racketeering charges, Connolly was initially saddled with obstruction of justice charges for helping Whitey Bulger evade capture —but neither of those crimes landed him a 40-year prison sentence. In 2008, just several years after serving the first chunk of his ten-year federal prison sentence,Connolly was convicted of second-degree murder in the state of Florida. Without a doubt, the turn of events is one of the more convoluted elements in Connolly’s fall-from-grace story. As depicted inBlack Mass, the FBI agent gradually looked the other way, eventually aiding Whitey Bulger’s criminal exploits.
Black Mass Review
Black Mass is an intriguing blend of classic gangster movie drama under the umbrella of an intimate Bulger biopic.
Although John B. Callahan was murdered by Winter Hill Gang hitman John Martorano in 1982, prosecutors pointed out that Martorano was acting on the orders of Bulger and his long-time associate Stephen Flemmi. The Winter Hill Gang criminals decided to put a hit out on Callahan only afterJohnConnolly informed them that the FBI was investigating the businessman’s ties to the gang, hence the second-degree murder chargesleveraged against Connolly. The trial’s judge noted that the former FBI agent had “crossed over to the dark side,” sentencing him to 40 years in prison in 2009 (viaCNN).
John Connolly Was Granted Parole In 2021
The Former FBI Agent Was Released From Prison On Medical Grounds
Before being granted parole in 2021, John Connolly’s second-degree murder conviction was a real roller coaster. Even after the sentencing, Connolly maintained that he wasn’t involved in the murder of John Callahan, either directly or indirectly. Nonetheless,when Connolly was released from federal custody in 2011, he was immediately transferred to a Florida state prisonfor the 40-year sentence for second-degree murder. While a 2014 appeal overturned Connolly’s murder conviction, it was promptly reinstated by a full court en banc the following year (viaThe Boston Globe). Still, the possibility of parole wasn’t out of the question.
Connolly was released from Florida state prison on medical grounds…
After serving a third of his 40-year sentence in Florida state prison, John Connolly became eligible for parole. The potential for parole added yet another wrinkle to an already-convoluted situation. In 2021 — a decade after finishing his federal prison sentence — Connolly was officially granted parole from prison in Florida. Reportedly,the parole came on the heels of prison officials learning that Connolly was gravely illand likely to die in prison if he stayed. Officially, Connolly was released from Florida state prison on medical grounds, with experts claiming he had roughly a year left to live.
Where Is John Connolly Now?
Connolly Lives In Massachusetts & His Health Is Improving
Released from Florida state prison in February 2021, John Connolly returned to his home state of Massachusetts. Despite his medical release, and status as “terminally ill,” the former associate of Whitey Bulger will remain under the supervision of law enforcement until 2047 (viaBoston Herald) — though he likely won’t live that long. Initially, medical experts said Connolly had just a year to live, but that was several years ago. Now in his mid-eighties,Connolly lives life on the outside and, despite his convictions, even receives a pensionfrom his time with the FBI.
As of 2023, experts speculate that John Connolly may return to prison if his medical parole is deemed no longer valid.
When Connolly was initially released on parole, officials deemed that Connolly was to remain confined to a hospice facility or residence unless he was seeking medical care for his terminal condition. It’s possible the added risk of COVID-19, which spread more easily in confined spaces, was another reason officials agreed to Connolly’s parole. However, according to theBoston Herald,the agent-turned-mob-informant’s health seems to be improving, which is prompting officials to revisit his parole. If John Connolly is well enough to serve the remainder of his prison sentence, theBlack Masssubject’s parole may be reevaluated.
Sources:The Guardian,CNN,The Boston Globe,Boston Herald
Black Mass
Black Mass is a crime drama biography based on the true story of one of the most notorious criminals in U.S. History, Whitey Bulger. When Bulger’s turf is encroached on by a rival mafia family, the Angiulo brothers, the death of one of his own mafia family members leads him to join his long-time friend and become an informant for the FBI to exact his revenge - and push the Angiulo’s out of his turf.
