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This weekend sees the release of the documentary Whitey: United States of America v. James J. Bulger, the latest addition to the robust sub-genre of books, plays, movies, TV shows and column inches dedicated to telling tales of the FBI’s one-time second Most Wanted, Boston gangster James “Whitey” Bulger.
Joe Berlinger’s film focuses on the build up to the 2013 trial of the iconic criminal, exploring what will possibly be the final chapter in the decades-long Bulger narrative. For the first time in the years of media coverage, we hear Bulger’s quietly authoritative voice (speaking to his attorney over the phone), insisting that whatever we think his story is, we might have got the facts wrong.
It’s unnerving to hear the man behind the myth speaking directly. While he was South Boston's undisputed crime kingpin, Bulger lurked in the shadows as the ultimate boogeyman, a remorseless killer and extortionist no one dared cross, letting his fearsome reputation do the talking. During his sixteen years as a fugitive, his ex-cronies did the talking for him, filling in the dates, names and places of his quarter-century crime spree without fear of contradiction. Their tongues were loosened when Bulger was outed as an FBI informant, tattling on his friends and rivals since 1975, violating the gangster code and laying himself open to disloyalty. As a fellow prisoner allegedly told Bulger associate Kevin Weeks while he considered whether or not to dish the goods on his boss, "You can't rat on a rat."
For the longest time, therefore, the James Joseph “Whitey” Bulger, Jr. narrative was woven by others, all intent on making him fit their archetype. No one who’d known him was interested in making objective observations. Instead, they painted him in as terrifying a light as possible — always the worst bad guy in the room — in order to save their own skins. Did they draw on paradigms from fiction as well as memory? No one knows. Other than the crucial ‘dirty rat’ detail, the messy tangle of Bulger myths generated after his disappearance read like classic gangster lit.
Urban Legend
Bulger was the one who set his story in motion. From the get-go, he was aware of how to create a public persona and how he wanted to be perceived. A savvy Southie kid, he early on decided crime offered more profit, more kudos and more long term potential for leadership positions than anything else on offer to a working class stiff, and threw his lot in with the local Shamrock gang. He cut a deliberately colorful figure round the neighborhood, flush with ill-gotten cash, walking his pet ocelot or driving a car along the railroad tracks. He bolstered his reputation as a hometown hero by buying ice creams for local children. He worked his way steadily up the ladder from delinquency to professional criminality, graduated from street muggings and shaking down rent boys to robbing banks, for which he was jailed in 1956.
Serving federal time inside the Atlanta Penitentiary wasn’t easy. Hoping to reduce his sentence, he agreed to take part in a series of psychological experiments. No one at the time knew that these experiments, part of the CIA-funded MKULTRA program, involved giving subjects increasingly dramatic doses of LSD — the participants thought they were helping research a cure for schizophrenia. Bulger stopped sleeping and started fighting, and years later, claimed he suffered from PTSD. He went from wannabe model prisoner to identified troublemaker, and served three years of his sentence in the nation's most infamous high security institution, the Ivy League for hard men, Alcatraz.
Bulger returned to the South Boston streets in 1965, moving back home with his dear old Mom. He was soon working as an enforcer, collecting gambling and loan payments from punters who, after one visit, tended never to be late with their paper bag of banknotes again. He took advantage of the bloody street warfare between the various Irish factions to rise through the ranks, opting for loyalty to Howie Winter and execution of his rivals. Once he achieved the desired leadership position, he upped the fearsome factor by teaming up with Stevie “The Rifleman” Flemmi, an Italian-American mobster with ties to both the Patriarca Mafia family, and Howie’s Winter Hill mob.
From the early 1970s until his flight from indictment in 1994, Bulger (along with his partner-in-everything, Flemmi) was at the center of organized crime in South Boston. He ruled the neighborhood as an archetypal American anti-hero, running rackets from fruit machines to racetrack fixes, truck hijacks to IRA arms shipments, along with extortion, torture and even murder of anyone who got in his way. Confident he would never be arrested, Bulger cultivated his classic-gangster-compliant mythos with care. Those who needed to knew he was a stone cold killer, capable of strangling a victim to death with bare hands or shooting at point blank range, before pulling out teeth and sawing off fingertips to prevent potential identification of the corpse. When he rolled into a target’s office and demanded $50,000 not to kill them, the unfortunate individual usually paid up without demur. Yet he could also be an affable host, showering friends and family with gifts, helping out neighbors in need, a role model and beacon of benevolent hope in the otherwise deprived Southie hood.
It didn't hurt matters that Jim’s younger brother, Billy Bulger, was one of the most powerful politicians in the state. Billy was first elected President of the Massachusetts State Senate in 1978, and was re-elected every two years thereafter to 1996 – the longest tenure in Massachusetts’ history.
Both brothers took the luck of the Irish to new extremes. Despite many attempts by local law enforcement to nail him to the wall, James Bulger always stayed one step ahead of the tails, the wiretaps, or the attempts to get his business associates to talk. Witnesses clammed up or disappeared outright. Police reports got lost in the system. Inquisitive cops found themselves threatened with demotion. Unbeknownst to his fellow wiseguys — especially the Boston Mafia — this Teflon effect came courtesy of his long-term status as an FBI Top Echelon informant. From 1975 onwards, Bulger stayed on top of the heap by providing insider information about Boston gangland activity, especially if it wore an Italian suit. The Organized Crime Squad’s avowed goal was to bring La Cosa Nostra down: they cared little about the crimes perpetrated by the Bulger and his cohort in the Winter Hill Gang.
Even when, finally, a warrant for his arrest was issued in 1994, Bulger knew exactly when to skip town and disappear into a carefully prepared new identity. For sixteen years he stayed off the radar, and, despite making the No. 2 spot (behind Osama Bin Laden) on the FBI's Top Ten Most Wanted list, he was able to enjoy a placid existence in a Santa Monica condo, before a tip-off from a tourist brought a SWAT team to his parking lot.
The Evil That Men Do
This is the stuff of legend – albeit a legend refracted in many different directions through selective reporting by Boston media, through the favorable spin put on Bulger's activities by his FBI handler, Special Agent John Connolly, and through the insinuations spread by Bulger himself about being a 'good bad guy', the gentleman gangster who didn't kill women or permit the sale of drugs on his turf. Audiences everywhere have lapped it up. After Bulger disappeared and his former associates started revealing where the bodies were buried as part of their plea deals, a publishing cottage industry grew up to fuel the demand for Whitey stories. There are many books extant about Bulger's vicious life and times, written by Boston journalists, true crime aficionados, and former trusted confidantes. Hollywood has muscled in on the action too: Bulger was the inspiration for Jack Nicholson's character in The Departed. Johnny Depp is currently in Boston filming an adaptation of Black Mass. Fox is developing a TV show based on Street Soldier: My Life as an Enforcer for Whitey Bulger and the Boston Irish Mob, a memoir written by a former member of the gang.
Why this obsession with one man's sordid criminal history? The answer, perhaps, lies in the neat nature of the narrative structure. Whether by accident or deliberate manipulation, the official Whitey Bulger story adheres precisely to the familiar gangster paradigm. It's a tale many times told, in fact and fiction, about a psychopathic kingpin who rules an underworld dominion. It's ripped from the lurid headlines about Al Capone, the Kray twins, Meyer Lansky, John Gotti, Dominic Noonan, Ned Kelly, Jack Diamond, Demetrius Flenory et al. It's glorified on the silver screen, in The Godfather, The Big Heat, Scarface, Goodfellas, Miller’s Crossing, Get Carter, Pulp Fiction et al. It’s embedded in the folklore of modern America, springing from the bloodshed of prototype gangsters, fêted outlaws like Butch Cassidy, Jesse James and Billy The Kid. Its origins can be traced back still further, to the 14th century ballads praising the deeds of O.G. Robin Hood, who wrote the manifesto for the “good bad guy” agenda claimed by Bulger: steal only from the rich, protect friends and family unto the point of death, and always play the gallant when there’s a lady in the house.
Any aficionado of the gangster genre knows that, often fatally, hubris is an essential part of the package. The arrogance, ambition and ruthlessness required to rise to the rank of capo del capo also, ultimately, spell the aspiring hoodlum’s doom. And so it was with Whitey. For years, no one questioned his impeccable wiseguy credentials. Everyone in South Boston knew James Bulger was a straight-up gangster — cross him, and live in fear for your life, but stay on his right side and he’d see you got your just rewards. Yet there’s only so long even the most adept manipulator can play both ends against the middle. In September 1988, a four-part story in the Boston Globe about the Brothers Bulger focused an uncomfortably bright spotlight on James and William, and devoted a whole installment to James’ rumored role as stool pigeon for the Feds. Whitey denied it categorically, as did the FBI, and it seemed, for a time, that the allegations were a storm in a teacup. But the rumors persisted about the unholy alliance between Bulger, Flemmi and Agent Connelly, and the infractions committed on both sides. It took almost another decade of legal and political maneuvering, but on June 3, 1997, the Justice Department officially disclosed that yes, indeed, James “Whitey” Bulger had been on their books as an informant since 1975.
Dishonor Among Thieves
That was when the canaries began singing, loud and hard. Remember, you can't rat on a rat. Bulger was gone — who knew where — and in his absence former trusted associates blurted everything they knew in the hope of scoring a shorter sentence. Information about where the bodies were buried also netted some lucrative book deals. Kevin Weeks, whom Bulger looked on as a son, served a reduced five-year sentence then spilled the inside beans in Brutal: The Untold Story of My Life Inside Whitey Bulger's Irish Mob (with Phyllis Karas). Also from the perspective of the post-prison straight and narrow, another enforcer, John “Red” Shea, penned Rat Bastards: The Life and Times of South Boston's Most Honorable Irish Mobster in tribute to his former boss. More lowly associates capitalized on their connection with memoirs such as the aforementioned Street Soldier, by Edward MacKenzie Jr. (also with Phyllis Karas), or (and this has to win Lurid Title of the Year) The Choir Boy: Why I Turned to a Life of Crime with the Whitey Bulger Gang after Being Raped by My Scoutmaster by Eric Schneider.
Pulp “Untold Story” paperbacks aside, several Boston journalists have also contributed book-length exposés of the case. Their investigations cover how Bulger’s reign of terror lasted so long without opposition, and how deeply implicated senior FBI officials were in their knowledge of the crimes he committed under an umbrella of federal protection. It's a story of corruption that goes right to the top.
Black Mass: Whitey Bulger, the FBI, and a Devil's Deal by the Boston Globe’s Dick Lehr and Gerard O'Neill is the basis for the Johnny Depp movie, and makes for a chilling read. It explores how Southie born-and-bred Connolly, who had idolized the charismatic Whitey as a child, was completely unable to draw the required lines in the sand. Connolly treated Whitey as a celebrity friend rather than a necessary evil, hanging out over wine and dinner, accepting gifts, and establishing a two-way flow of chatter that made it increasingly unclear who exactly was pumping who for intelligence. Over the years, Connolly exaggerated and downright faked reports about the supposedly vital information Bulger was feeding him about the local Mafia, keeping other law enforcement agencies off the gangster’s back, leaving him to rule South Boston, killing, torturing and extorting with impunity.
Published in 2000, Black Mass ends on the question, “Where’s Whitey?” Lehr and O’Neill’s 2013 follow-up, Whitey: The Life of America's Most Notorious Mob Boss explores the answer with gusto, drawing on court and family records, interviews and previously classified documents to paint a detailed picture of the life and times of Bulger up to and including his 2011 arrest.
Talk radio host Howie Carr’s The Brothers Bulger: How They Terrorized and Corrupted Boston for a Quarter Century widens the scope, bringing the other Bulger, Billy, into the loop. Carr traces the parallel histories of the two brothers growing up in Southie, one an altarboy with aspirations, the other a defiant teenage crook. How did they come to travel such different roads? The brothers admittedly share some similar qualities: they’re both born leaders, unwilling to tolerate rivals, adept at backroom deals, and loyal to their Southie roots. Carr wonders how much else the brothers shared over the years. What did the politician know about the psychopath’s activities, and vice versa? If one brother asked for assistance, how far would the other one go in bending the law to help him out? Unfortunately, when questioned on the record, Billy could never quite recall…
Living The Dream Lie
One has to wonder what “Charlie Gasko”, living quietly in a Santa Monica apartment thought of the media hoop-la surrounding the fast-developing Whitey mythos? He must have read the papers, seen the 60 Minutes segments, and — according to one tip to the FBI hotline — even snuck into a screening of The Departed. Yet there was nothing he could do about the tell-all paperbacks trashing his reputation. Charlie and his wife, “Carol”, were concerned with perpetuating another myth, that of the meek retiree couple who enjoyed evening strolls and bargain shopping. They smiled and said polite hellos to their neighbors, paid their rent in advance, in cash, and decorated their condo with cat figurines. They projected a persona that seemed unremarkable and harmless. Other than the note on their front door that said “Do Not Knock At Any Time Ever”, and Charlie’s occasional flashes of vicious temper, there was nothing that marked them as at all out of the ordinary, or suggested that a $2 million reward was being offered for their capture.
The neighbors noticed nothing amiss until June 22, 2011, when the FBI finally cornered Charlie in the parking lot. They had good reason not to confront the Gaskos inside the apartment; a search revealed more than $800,000 in cash stuffed into cavities in the walls, along with an impressive arsenal of guns and knives. Even at 82 years old, Bulger was still a very dangerous man. Angelenos take note: this former Gasko/Bulger residence, now (presumably) repaired, is currently up for rent, for almost three times what the Gaskos were paying. It seems the gangster's reputation even has an impact on LA rental hikes.
Whitey: United States of America v. James J. Bulger brings the Bulger story to its natural conclusion by giving an account of the trial, the last opportunity any 84 year-old mobster has to make his mark on the public record. Director Joe Berlinger, best known for his much-lauded work on the Paradise Lost series of films, admits to an ongoing fascination with the flaws in this nation’s criminal justice system and how they contributed to Bulger escaping punishment for so long.
As Bulger finally faced 32 counts of racketeering, money laundering, extortion, and weapons charges, including complicity in 19 homicides, many of those involved in the case over the past forty years thought the truth might at last come to light — about the scope of Bulger’s drug-dealing, the true number of his murder victims, and, above all, the magnitude and intricacy of the government corruption that enabled this gangster and his cronies to make his myths.
Bulger knew the only possible outcome of the legal proceedings against him was spending the rest of his life in jail, so he concerned himself with taking this last chance to define his legacy and wrest control of his reputation. The arguments of his defense team attempted to shift the main direction of the runaway Bulger narrative. They contended he had remained true to the gentleman gangster paradigm, and was never a rat. He saved a federal prosecutor’s life in order to earn FBI protection. Special Agent Connolly’s files naming him as an informant were faked, a desperate operator’s attempt at credibility for his anti-Mafia crusade. These claims may sound outlandish but, as the film shows, a plausible deniability argument exists.
Inevitably, perhaps, the narrow scope of the trial failed to deliver a definitive version of the convoluted narrative, disappointing many of the stakeholders who turned up at the courthouse every day. Berlinger gives a voice to some of these dispossessed, the families of Bulger’s victims still seeking justice for their lost loved ones who, if the FBI hadn’t been so determined to protect its sources, may not have become victims of Bulger’s terror-inducing rampage. The prosecution focused on Bulger and Bulger alone, and the Department of Justice may never answer for its part in his crimes.
Bulger’s version didn’t prevail either. At the last minute, he refused to take the stand and give his account of events, denouncing the trial as a “sham”. Try as he might, he was unable to carve his enduring legacy into shape he wanted; the stand-up wiseguy who had the Feds in his pocket, not the other way around. Nor did he get to choose who would play him on the big screen. He picked Mark Wahlberg. The producers of Black Mass went with Johnny Depp. Sometimes the myths we make evolve beyond our reach, no matter how hard we try to bend our personal narrative to the desired paradigm. Truth has a habit of trumping our most cherished fictions. Serving two life sentences, Bulger will live out his few remaining years in USP Tucson, a once-feared gangster forever — whether the accusations are true or not — notorious as a dirty rat.
WHITEY: United States of America v. James J. Bulger, the latest documentary from Academy Award-nominated director Joe Berlinger (Brother's Keeper, Paradise Lost, Metallica: Some Kind of Monster) was released in New York on June 27 and on VOD, followed by a national roll-out, including Los Angeles on July 11.
Unfictional: The Couple In 303, produced for KCRW by Gideon Brower and Eric Drachman
About the author
Karina Wilson is a British writer based in Los Angeles. As a screenwriter and story consultant she tends to specialize in horror movies and romcoms (it's all genre, right?) but has also made her mark on countless, diverse feature films over the past decade, from indies to the A-list. She is currently polishing off her first novel, Exeme, and you can read more about that endeavor here .
