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Snitch on Snitch on Snitch - What to Expect from the Whitey Bulger Trial

This week, the racketeering and murder trial for infamous Boston mobster James "Whitey" Bulger finally began, roughly 18 years behind schedule. Bulger fled Boston based on a tip from a childhood friend that the Feds were finally coming after him. And...
Κείμενο John Liam Policastro

Photo via Wikimedia Commons This week, the racketeering and murder trial for infamous Boston mobster James "Whitey" Bulger finally began, roughly 18 years behind schedule. Bulger fled Boston based on a tip from a childhood friend named John Connolly that the Feds were finally coming after him. Connolly himself was a newly retired FBI agent who, it turns out, had made Bulger his top-echelon informant in 1975. This move would prove to be a mutually beneficial deal between two devils. Based on Bulger's tips, the Boston Mafia (the Bulger gang's archrival) was obliterated in a string of victories for Connolly and the Boston branch of the FBI. Due to Connolly's protection, Bulger was able to lie, cheat, steal, and even allegedly kill his way to the top of Boston's underworld.


Of course, Bulger—who has plead not guilty to the 32 charges, including 19 counts of murder—and his attorney, J. W. Carney are hammering away at many of these charges and accusations and have a pretty good defense. Why? Because Bulger had a complicated and still mysterious relationship with the FBI’s star witnesses: they are all admitted killers, confidants, or even former members of Whitey’s gang. In other words, the crux of this trial will basically be a long and legal reenactment of the final standoff in Reservoir Dogs, with Bulger, the FBI, and former mobsters Steve "the Rifleman” Flemmi, John Martorano, and Kevin Weeks pointing bloody accusations at one another while still all collectively admitting some acknowledgements of guilt of their own. An even more ironic twist has this all going down in a federal courthouse located in South Boston, the neighborhood he grew up in and where he ultimately became the judge, jury, and even executioner, according to prosecutors.

Although the Whitey Bulger tale is a long and lurid legend in Boston, it became a national story shortly after he fled ahead of a racketeering indictment and his secret history with the FBI emerged in 2000. Whitey was even on the top of the FBI's most wanted list and only replaced by Osama bin Laden after the 9/11 attacks. He was finally apprehended in June of 2011 thanks to a shadowy tip to the FBI while living in plain sight in a Santa Monica condo with weapons and cash stashed in the walls under the name Charles Gasko. Having remained a huge story in the local press ever since, jury selection delayed the start of the trial, with some 800 people crammed into the selection to find 12 fair and impartial people. One alternate juror actually fell asleep during prosecutor Brian Kelly's opening statement laying out the government's case against Bulger and asserting that he was a "hands on killer" stretching back 30 years. Defense attorney Carney and Bulger dispute these murder allegations, maintaining that while he certainly made millions upon millions of dollars over the years through drugs, gambling, and loan-sharking, he was not a killer. Bulger instead insists that the murders are being pinned on him and were perpetrated by the men testifying against him and shouldn't be believed.


Flemmi was Bulger's right-hand man and a fellow informant for Connolly. Flemmi is already serving a life sentence for multiple murders and avoided the death penalty by cooperating with the FBI against Connolly, and Connolly is serving a 40-year sentence for his corrupt career, including a second-degree murder conviction for tipping Bulger and Flemmi off about World Jai Alai business owner Roger Wheeler going to the FBI when he discovered Bulger's gang conducting an embezzlement scheme through his business. Wheeler was murdered. Wheeler was in fact killed by Martorano, who also admitted to 20 other murders of his own and received a scant 15-year sentence for his testimony against Bulger and ultimately only served six years and has since become an author. Two of the other 19 murder charges were young women named Deborah Davis and Deborah Hussey who had romantic relationships with Flemmi, who claims he witnessed Bulger separately strangle both women to death in a South Boston basement, though Flemmi admits he even pulled Hussey's teeth out of her lifeless head before dumping her body in a makeshift grave dug by Kevin Weeks, who received five years for his cooperation with the government.

Confused yet?

Prosecutors also described the grisly last moments of Arthur "Bucky" Barrett's life. The small-time thief was lured to the same Southie basement by Flemmi and Bulger, chained to a chair, and tortured so he would give up the location to a large stash of money he had stolen before being shot to death by Bulger. Kelly noted that Bulger was alleged to have joked, "Barrett's going downstairs to lie down for a while," as he marched the doomed thief to his death. During this testimony, Bulger sat silently and emotionless staring straight ahead as he has largely done for most of the week, except for snickering, right when ex-bookie Dick O’Brien recalled a death threat Bulger made to a man who owed him money.


An early mug shot of young Whitey.

However untrustworthy his accusers are his is still a very long-shot defense. Carney even stated that not only is Bulger not a killer, but he was also never an FBI informant, citing Bulger's Irish heritage and insisting "the worst thing that an Irish person could consider doing was becoming an informant." Carney also insisted that Bulger couldn't have been of use to the FBI because he really had no associations with the Italian run La Cosa Nostra, an assertion quickly struck down by the prosecution as they showed grainy surveillance footage of Bulger meeting with one-time Boston Mafia head Donato Anguilo back in 1980. Anguilo was one of the many major mafiosos in Boston and Providence to be brought down by the FBI during the mid-1980s thanks to information Bulger and Flemmi gave up snitching. Bulger insists he merely gave large sums of money to Connolly and scores of other local law enforcement officials in the city as routine payoffs as he took over the Boston underworld.

Retired State Police Col. Thomas Foley, who began the investigations over 20 years ago that led to these sweeping indictments, also testified that Bulger was an FBI informant and stated that the corrupt Boston FBI office  was thwarted. Jurors have also been shown large caches of machine guns and other large arsenals of weapons seized by authorities and attributed to Bulger, though the defense got Foley to admit that none of Bulger's fingerprints or DNA have been found on any of them. Most of the testimony on Friday was from aging Boston bookies from the 70s and 80s detailing how Bulger and his crew shook them all down with iron fists. None of this proves that he killed anyone, although he is alleged to have actually killed 40 people in his lifetime starting with the bloody Boston gang wars of the 1960s when many Southie gangsters and rivals were wiped out shortly after Bulger was released from prison—he is an Alcatraz alum—for various robbery and hijacking charges. It is also interesting to note that while he is steadfastly maintaining he'd never have worked with the government, he was actually a willing volunteer for the CIA's infamous MK-Ultra mind-control experiments and allegedly fed LSD while an inmate in the federal penitentiary in the late 1950s as a way to reduce his sentence, according to one-time protegé Kevin Weeks, though I doubt we will see an electric Kool-Aid acid gangster defense emerge.


There is still much more to come, but the main event will surely be the long-awaited trilogy of testimony from Flemmi, Martorano, and Weeks against Bulger. Notably absent from the stand is Whitey’s younger brother, William "Billy"  Bulger, who rose to the top of the Boston political world while his older brother simultaneously rose to the top of the Boston criminal world, becoming the Senate president for years and eventually becoming president of the University of Massachusetts. He was infamously forced to resign from that post when it was revealed he had been in contact with his brother while he was on the run, even defiantly telling a House committee in 2003, "It's my hope that I'm never helpful to anyone against him," before invoking his Fifth Amendment rights. With a spotty roster of twisted witnesses and a well-documented history of FBI corruption amid more embarrassing national spying scandals, this is surely the government’s trial to lose.

The trial will last all summer. Stay tuned.


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