So Much For Whitey Bulger

So ends one of the most fascinating and destructive stories in the annals of US organized crime.

What makes the rampage of the Boston, MA underworld personified and long led by James "Whitey" Bulger such a compelling history is that it was actively enabled by the FBI and by the US Congress, in the person of John William McCormack.   McCormack began his association with the Boston underworld and the FBI as an attorney during Prohibition representing the Gustin Gang, bootleggers from Boston.   When elected to the US House he began looking out for the Massachusetts State Senate seat to which young Billy Bulger was elected. 

McCormack also looked out for Billy's older brother, Whitey.  When Whitey served in the USAF he was court-martialed and openly told his accusers that McCormack would keep him out of trouble.   Whitey began male prostitution activities as a teen and in the 1950s went to prison after a string of bank robberies; McCormack worked to lessen Whitey's hardship in his nine years in prison.   After getting out of prison in March 1965 Whitey was given a no-show job as a janitor for Suffolk County, and before retiring in January 1971 McCormack instructed FBI boss J. Edgar Hoover to develop Whitey as an informant.

A month later Whitey, who by this point was a member of the Killeen Gang of Boston, was with a fellow gangster, Billy O'Sullivan, and O'Sullivan shot Buddy Roache, a member of the Mullen gang of Boston; Whitey was never indicted because when police tried to obtain arrest warrants they were rejected by the South Boston District Court - this thanks to Billy Bulger.

The FBI in 1961, on orders of then-new Attorney General Robert Kennedy - this to cover up his father Joe's long criminal career as well as his own relationships with gangsters such as Chicago's Sam Giancana - began developing informants to take down the Mafia.   In Boston agent Harold Paul "H. Paul" Rico was in charge of this task.   Rico was an FBI agent but he walked, talked, and acted like a gangster, and took a personal hatred of another Boston area gang, the gang of the McLaughlin brothers.   Rico's treachery was first shown when gangster Ronny Dermody, who'd once been arrested by Rico, went to him for help; Rico set him up ostensibly for a meeting - instead Rico sent rival gangster Buddy McLean to kill Dermody, then shielded McLean in his house in Belmont, MA.

Rico developed the Flemmi brothers - Vincent James "Jimmy The Bear" Flemmi and his younger brother Steve - as informants when they were apprentice gangsters working for the Bennett brothers, specifically Edward "Wimpy" Bennett.   Rico also developed psychopathic gangster Joe "The Animal" Barboza as an informant, and in March 1965 they killed minor mobster Edward "Teddy" Deegan; Rico made sure Barboza and Jimmy The Bear would not be indicted, and Barboza fingered four rival gangsters with Deegan's murder - the result was four men framed by the FBI spent some thirty years in prison, and it wasn't until the late 1990s that the FBI was exposed as sending to jail four innocent men to cover up for snitches of theirs - among the agents perpetuating the coverup was Robert Mueller, presently investigating President Trump and getting nowhere with it.

By 1972 with gang war raging, Whitey arranged a meeting with infamous Boston hitman Johnny Martorano, who was with one of the strongest gangs in the area, based in Winter Hill in Somerville.  Martorano was friends with Howie Winter, the gang's leader, and he felt he owed a favor to Billy O'Sullivan.   As a result, Whitey was brought into the Winter Hill Gang.  In this time of the early 1970s Whitey was finally developed into an official FBI informant working for John Joseph Connolly, who'd spent his life getting favors from Billy Bulger and who apprenticed with Rico. 

Connolly now served as point man for protecting Whitey Bulger, and in the 1970s the Winter Hill Gang became involved in extortions, race-fixing, and sports betting among whatever racket they decided to become involved with.  Their strength increased in 1974 - Steve Flemmi years earlier had been allowed to escape prosecution by the FBI, helping him move to Montreal under an alias.   In 1974 the FBI brought him back to Boston to continue as an FBI snitch.   Steve Flemmi was soon taking up with teenage girls such as Deborah "Debbi" Davis, who worked for a famed Boston-area dealer in stolen items, and he also had a wife in Marion Hussey, but it was her daughter Deborah who bore brunt of sexual aggression by Steve; also imposed upon by Steve was Debbi Davis' younger sister Michelle.   Michelle would die of an overdose around 2006, but Debbi was murdered by Whitey and Steve when she became tired of being part of Steve's harem; Debbi had a cousin, Eva "Liz" McDonough, who was girlfriend of gang member Nick Giso; when she demanded answers from Steve about her cousin's disappearance Whitey and Steve tried to set up her murder - and missed.

Whitey-involved murders rampaged in the Boston area in the 1970s.   A rival gang led by Al "Indian Al" Angeli and his brother "Indian Joe" Notarangeli was killed in the 1973-74 period - this as a paid favor to Mafia boss Gennaro "Gerry" Angiulo, and at least one innocent bystander was gunned down by mistake in this gang conflict.  A former friend of Whitey, Tommy King, was murdered and later that same night King's friend, Francis "Buddy" Leonard, was killed.  Club owner Richie Castucci had participated in the gang's sport betting operation, but when the gang hid two of its members out in New York City, Castucci - himself an FBI rat - told his Buearu pals; Connolly got word to the gang and at the end of December 1976 Castucci was murdered; Connolly covered up the murder by claiming it to be the work of the Mafia - "Winter Hill doesn't kill like that."

When Anthony "Fat Tony" Ciulla, the Winter Hill Gang's master race-fixer, was indicted in the late-1970s Zip Connolly and the similarly corrupt head of the Bureau's Organized Crime Strike Force in Boston, Jeremiah O'Sullivan, made sure to cut Whitey and Steve Flemmi out of indictment - this as everyone else went down. 

Their master hitman Johnny Martorano was tipped to the pending indictment and fled to Florida, sustained there by Whitey and the FBI as an ace-in-the-hole.   Zip Connolly meanwhile fought to protect Whitey when the FBI tried to terminate him as an informant; this stemmed from MA State Police surveillance efforts continually frustrated because Connolly was tipping Whitey to them.  Connolly and Jeremiah O'Sullivan wanted Whitey and Steve as informant to justify a massive bugging operation at Gennaro Angiulo's headquarters on Prince Street in Boston.

The operation led to Angiulo's 1983 arrest, but in the meantime Whitey directly instigated or helped instigate other murders.   Another Connolly informant, a flamboyant drug lord named Louie Litif, killed one of his dealers and a witnessing bartender; Connolly covered up this murder and this was established when his letter to the insurance company of the bartender's family was presented as evidence in his later racketeering trial.   Litif was then killed himself by Whitey with help from another gangster, Brian Halloran, who himself would be killed at Whitey's behest in 1982. 

Part of the reason for Halloran's murder is he'd been involved in the murder or Roger Wheeler, a businessman who'd purchased the gaming company World Jai Alai, that had been owned by businessman John Callahan.   Callahan was ousted because he was hanging out with Winter Hill members and had been quietly giving money to them.   Wheeler retained as head of security former FBI agent H. Paul Rico, but soon discovered he was being skimmed.   He accelerated his investigation when one of his cashiers, Peggy Westcoat, who may have known who was involved, was murdered with her boyfriend in 1980.   Whitey, Steve, and Rico commissioned Martorano to kill Wheeler and thus keep them all out of jail.   Not until 2004 would Rico finally face indictment for instigating Wheeler's murder.

In 1980 a gang that included cops robbed a Medford, MA bank and stole what turned out to Angiulo cash.   The leader, Arthur "Bucky" Barrett, returned the money to Angiulo upon learning who it belonged to, but in 1983 Whitey and Steve grabbed him, extorted $60,000 from him, then killed him.   He was buried in the basement of a house the two owned in South Boston, and Barrett's two sons never recovered, killing themselves years later.  Around that same time Whitey and Steve killed Deborah Hussey, Steve's stepdaughter, because she'd confessed to Marion Hussey that she'd been fellating Steve; she was buried in the same basement. 

Then in 1984 Whitey got involved in drug running, though a weed importer named Joe Murray.  His gang tried to smuggle seven tons worth of Whitey-supplied weapons to the Irish Republican Army, but their boats were grabbed.  The DEA, unaware of the corruption of the FBI, revealed they were tipped by a gang member, John McIntyre.  Upon learning this from the Bureau, Whitey killed him.

Whitey's protection didn't end with the FBI - Boston's largest paper The Boston Globe effectively covered up for Whitey, claiming him to be innocent and repeating the line "he kept the drugs out of Southie."   Only in 1988 did the Globe acknowledge he had a "special relationship" with the FBI.  Billy Bulger, meanwhile, had become as Mass Senate President the de facto governor of the state and steered money his way while working to keep Whitey and others out of trouble; he'd even tried to get Zip Connolly appointed as Boston Police Commssioner, and when Whitey telephoned him Billy refused to inform police of such calls, despite being required to do so as an officer of the court.  Billy also stonewalled a grand jury in 2001 about helping his brother, a federal fugitive.  He finally testified before Congress under a grant of immunity, the same deal Whitey's fellow gangsters got before testifying, and even then lied in claiming ignorance.

In 1990 after busting wannabe Mafia boss "Rubber Lips" Patriarca, Connolly retired from the FBI and was given a politically-connected utility security job.   But in 1995 the feds, by now recognizing to keep the FBI out of it, handed down indictments to Whitey and his gang; Whitey fled, having spent twenty years establishing aliases and setting up safe-deposit boxes around the world.

Handling the trial was Judge Mark Wolf, a former member of the office of attorney William Weld before Weld was elected Massachusetts governor; Wolf had directly or indirectly witnessed when Jeremiah O'Sullivan worked to cover up for Whitey and Steve, and thus Wolf was the one who forced the FBI to admit the two gangsters were informants and to turn over old documents - it was these documents proving Whitey and Steve had set him up all these years that caused Johnny Martorano to finally turn on his former friends and expose them for what they were.   And by the time of Whitey's 2011 arrest Connolly and Flemmi were convicted criminals and Rico was dead. 

And now Whitey is gone, responsible directly or indirectly for some 59 murders and unknown millions of dollars stolen - all enabled by the FBI at the behest of a crooked US House Speaker.

The cliche still works - you can't make up this stuff.