Whitey Bulger POSTER

Boston: The City That Always Sucks

The embarrassing legacy of Whitey Bulger as told by two native sons

In Boston, life is often viewed in terms of how much (or how little) things suck. We know because we grew up here, and like many in this city of less than a million people, the two of us met on opposite ends of a brawl. For no reason whatsoever, we punched each other in the face outside an old Boston punk club in 2001. The cops showed up, did nothing. It was just another bullshit night in suck city, as the writer Nick Flynn once put it. Something typical. Nothing like what’s been happening here lately.

Over the past few months, a series of gruesome crimes has left a dark pall over this Puritan city on a hill. In April, two wannabe jihadi fuck heads allegedly detonated bombs during the Boston Marathon, killing three people and injuring hundreds more. Last month, Aaron Hernandez, an overpaid tight end for the New England Patriots, allegedly murdered his friend (and possibly others). Even more recently, police arrested Edwin Alemany, a South Boston man who stands accused of killing a young woman, punching another in the face and stabbing a third—all on a Wednesday morning.

Yet when it comes to pure, sociopathic “Masshole” murder, James “Whitey” Bulger, the crime kingpin who once tyrannized South Boston, stands a body bag above the rest. On Monday, a jury convicted Bulger on a bevy of racketeering charges and for participating in 11 murders. What made Whitey’s reign so terrifying isn’t just that he ran the city’s underworld—strangling and shooting his victims, then taking a snooze while his lackeys disposed of the bodies. It’s that the killing was sanctioned by the FBI, and that Whitey managed to masterfully manufacture such a good-guy gangster persona that even those who hated him often added to his lore. Many here in Beantown saw him as a hero, an Irish-American Robin Hood who fought for them against the powerful Italian mob. In some ways, Bulger encapsulates Boston, in all its corrupt and masochistic contradictions. “Many families were devastated by the drugs and crime,” Michael Cassidy, a former state prosecutor, told the The New York Times on Monday. “It’s important for the city not to have a false memory of what was going on.”

We grew up both terrified and enamored with Bulger. So as the trial ensued, we couldn’t resist periodically returning to Boston to watch it unfold. In the spirit of unity (we squashed our beef a long time ago), we decided to work together, bumming around both the trial and Southie, Bulger’s old stomping grounds. We wanted to see how Whitey’s fall had affected the city. We also wanted to score some crack. It seemed like a good idea.

How the authors bought crack

You can still get high wherever, even in a semi-public alley in the heart of Whitey’s old hood. No teeth required. We bought crack in broad daylight on a Sunday afternoon in front of a bar while a cop car idled nearby. It only cost $10, and as far as we could tell, it looked like some decent rock. One of our friends was smoking it late one night in the Boston Common, when a gang of crackheads stole one of our iPhones. They didn’t, however, get the rest of the drugs. Later, as one of us stopped into a convenience store to use an ATM, a cab driver drove away with our belongings in tow.


During one of our trips from New York City, we stopped at Fenway Park to watch the Red Sox play the Yankees. Fenway is Boston in building form: It’s old, small and filled with angry men. Part of being a Boston baseball fan is rooting for someone and something that sucks. Fans both love and hate the Sox like they both love and hate Bulger (or at least his myth). Both are losers who have made us completely miserable, but they are our losers, and that matters more than anything else. Complaining about the World Series curse or indulging a bar full of drunks with a bunch of fake Whitey stories to sound tough is a rite of passage here, an integral part of the city’s identity.

Whitey Bulger Court Drawing
(Jane Collins/Reuters)

The Sox won in extra innings, and the Fenway franks were delicious. But there was something different in the home of Williams, Boggs and Martinez. Maybe it was the dark cloud hovering over the Green Monster, the stench of stale beer wafting up from the stands or something in the city’s dirty water supply, but we knew something was wrong when the Bronx Bombers lost on Lansdowne Street and we couldn’t even make a steroids joke about A-Rod.

There were too many shitty brosefs—both the sausage-faced townies in tracksuits and the fat yuppies in their baggy khakis and powder blue polos—out in full force, whistling at our female friend, making gentlemanly comments like “Hey bitch, let’s fuck.” People kept trying to fight us. One guy even tried to fight us while he was taking a dump. The lyric little bandbox, as John Updike once called Fenway, had turned into a UFC-style Octagon. And we wondered if somehow Whitey was responsible, even behind bars. Maybe while Boston’s most notorious gangster faced a jury of his peers, the ghosts of the past were haunting the city that always sucks, somehow making it worse, more tense.


The Bulger trial was held at the John Joseph Moakley Courthouse, a boring bureaucratic-looking building near the once decrepit Boston Harbor, just yards away from where Whitey and his scummy friends once ruled the streets—with at least tacit approval from the feds.

Federal criminal trials are not televised, so in order to watch this Southie soap opera we had to show up early. Unfortunately, we often got stuck in the overflow room, watching the trial on closed-circuit televisions. As the trial ensued, rose-petal-perfumed grannies were always interrupting the testimony, yelling things like “What did he just say?” There was always an old guy who shuffled over to a television and turned up the volume like he was at home watching Matlock.

Standing in the courtroom, jailbird Whitey, a small, gray and shriveled man, the human embodiment of a mold-covered raisin, didn’t live up to his myth. He no longer looked like the swaggering savage from the legendary mug shots. Gone was suavely styled hair, the wide-brimmed hat. Instead, his clothes were rumpled and looked like something out of Jerry Seinfeld’s closet; in court one day he wore a blue dress shirt, baggy stonewashed jeans and chunky white sneakers. Known to be obsessed with health and fitness, the 83-year-old reportedly did dozens of pushups every day in his cell, but he was often the last man to rise in front of the judge, and spent most of his time doodling and looking bored.

It wasn’t boring though to watch his reputation get punctured. Bulger’s lawyers admitted that Whitey murdered people, ran the city’s drug game and extorted tons of people. Instead, their defense was all about Whitey’s legacy and some baffling code of honor: that he never murdered women, that he wasn’t a rat for the feds, and that he never sold heroin, just coke, as if that’s somehow better. (According to the testimony of at least one former drug dealer, Whitey’s blow was terrible. Compared with drug kingpins in New York City, he was also allegedly easy to rip off.)

Whitey Bulger Goat
(U.S. Attorney's Office of Massachusetts/Reuters)

Whitey didn’t always seem like such a clown. His rise began at the tail end of the brutal Boston gang wars of the 1960s. Fresh off a quick bid in Alcatraz for bank robbery, Whitey took advantage of the chaos. He and his buddy Stephen “The Rifleman” Flemmi started working with a corrupt FBI handler named John Connolly, who also happened to be the boyhood friend of Whitey’s younger brother, William Bulger. The same William Bulger who was once the president of the Massachusetts State Senate and the University of Massachusetts.

The younger Bulger may or may not have helped Whitey (he didn’t respond to a call for comment), but he didn’t really have to. The elder Bugler had help from the boys at the Bureau, the very people whom you’d think would be putting him behind bars. By the early 1980s, the FBI under Connolly’s lead allegedly gave Whitey and his Winter Hill Gang a free pass to do whatever they wanted—murder rivals, send arms to the Irish Republican Army, extort a bunch of drug dealers, basically terrorize the city—as long as he gave them intel on the Italian mob. As Michael Kendall, a former federal prosecutor who investigated some of Bulger’s activities, said in an interview with The New York Times on Monday“This was the worst case of corruption in the history of the FBI.”


In 1994, Whitey’s free pass expired. The state police, who had long distrusted the bureau on Winter Hill Gang-related matters, built their own case against the King of Southie. And soon Bulger was forced to flee ahead of an indictment, thanks to a tip from Connolly, 73, who will likely spend the rest of his life behind bars in Florida for Bulger-related crimes.

For 16 years, Whitey remained on the run, spending most of that time with his girlfriend, Catherine Greig, under assumed names in a modest, rent-controlled apartment near the beach in Santa Monica. Over the years, there were a host of Whitey sightings in Southern California. One was even at a screening of The Departed, Martin Scorsese’s 2006 crime film, which was at least partly based on Bulger’s relationship with the FBI.

In May of 2011, after Seal Team Six killed bin Laden, Bulger climbed to the top of the FBI’s Most Wanted List. He had a $2 million bounty on his head, and yet he was basically living, sans plastic surgery, in plain sight, roughly 4 miles from the Bureau’s Los Angeles office. That’s such a big question mark that many in Boston think the feds didn’t want to find Bulger. That he knew too much about their corruption, their lies. The FBI has vehemently denied this charge, though many in Boston (us included) think they’re full of shit.

Perhaps in response to the public criticism, the feds went after Whitey with a vengeance after tossing bin Laden’s body into the Indian Ocean. And when he was captured, some Boston residents were happy to see Bulger in shackles. Others, perhaps still in denial over his barbaric crimes, were disappointed. We’re embarrassed to admit it, but we also thought Whitey was kind of a cool guy, the last real American outlaw, an old-school boss who beat the mafia and the G-men at their own games. As the trial progressed, however, it was clear that we were wrong; that Whitey, far above everything else in this second-rate city, was the worst.


The most explosive moment of the trial occurred in July, over an assault on someone’s criminal honor—two words that rarely belong together. Bulger’s attorney Jay Carney called Whitey’s former protégé Kevin Weeks a rat. Weeks freaked out and called Bulger “the biggest rat of all.” And in perfect Boston English, Whitey then taunted Weeks, shouting “You suck!” before they both yelled “Fuck you!” at each other, just like all the nice people we met at the Sox game.

During the trial, Bulger also traded expletives with Flemmi, his former partner in crime and another star government witness. The two stared each other down in the courtroom, and later, a smug, smiling Flemmi mouthed “mothafucka” at his arch rival as he stepped down from the witness stand. Bulger vs. Flemmi was the Magic vs. Bird of maggots: Two of the most deceptive, successful criminals in modern American history were essentially blaming each other for, well, everything. They hadn’t seen each other in 18 years, and suddenly they were calling each other pedophiles. Bulger allegedly snuck off to Mexico with a teenage girl (something he denies), and under oath, Flemmi admitted to receiving “consensual” blowjobs from his stepdaughter, Deborah Hussey, whom Whitey was convicted of killing.

Bulger was so ridiculous that his lawyers were forced to resort to shameless sympathy measures. They released photos of Whitey with a variety of pets, including parrots and even a goat (a fucking goat!). If that wasn’t bad enough, Bulger’s attorneys also offered a photo of Whitey sitting with a priest as if he was a real man of God. That priest turned out to be Monsignor Fred Ryan, the former vice chancellor for the Boston Archdiocese, who was later defrocked for allegedly molesting little boys in the early 1980s, around the time the photo was taken and Bulger was in cahoots with the Bureau.


Southie has changed considerably since Whitey’s fall. The neighborhood has been gentrified, and now boasts ugly glass condos, yuppies walking tiny dogs and the Institute of Contemporary Art, a museum that regularly features horrible shows like Shepard Fairey: Supply & Demand.

Overall, the city’s crime rate has plummeted since Whitey fled. But thugs and drugs still rule in Southie. While we were in town, a 27-year-old man was convicted of beating a grandmother to death with a baseball bat. She had prescription pills and he wanted them.

Whitey Bulger Younger
(U.S. Attorney's Office of Massachusetts/Reuters)

We feel for this city for what happened at the Boston Marathon, but our experience here made it clear that post-Whitey Boston is a city with post-traumatic stress disorder, a place forever scarred by Bulger’s crimes, forever diminished by losing, whether in the streets, in the courtroom or out on the diamond. (Today the Red Sox are in first place, and already no one thinks the team’s success will last.) The Bulger trial ended with a conviction, and helped bring out the truth about Whitey, but no one really knows how to celebrate. People here don’t seem to realize that being strong isn’t as important as being kind, or showing others respect. Instead, a spirit of fatalism and false triumph has infected this city, a place where Whitey never once took the witness stand.

In perhaps a perfect climax to the trial on Monday, Bulger, the fallen king of Southie, was walking out of the courtroom when he turned to his family and offered a thumbs-up. Like it was all good. A woman sitting nearby responded by yelling “Rat-a-tat, Whitey!” as if heckling him was more important than justice, as if working for the feds was somehow worse than being a murderer. We wish we could say it was just another bullshit day here in suck city. But it wasn’t. It was something else.

Ray LeMoine was born in Boston and lives in New York. He is the co-author of Babylon by Bus: Or, the True Story of Two Friends Who Gave Up Their Valuable Franchise Selling Yankees Suck T-Shirts at Fenway to Find Meaning and Adventure in Iraq, Where They Became Employed by the Occupation in Jobs for Which They Lacked Qualification and Witnessed Much That Amazed and Disturbed Them.

John Liam Policastro was born in Boston and lives in Brooklyn. His work can be found via Google search.

Respond Now
  • Terrible representation of Boston, almost fantastical. Not Accurate.

  • should of just stayed in New York. I’m not going to insult New yorkers since I know many and they are fine human beings. you shouldn’t let one or two people put the entire city into a stereo-type. its just ignorant, there are dicks all over the place, including New York

  • An incredibly self-indulgent story by an obvious pair of shitheads. And very accurate.

  • Pretty crazy

  • I can’t remember the last time I saw a fight at the Disney Land that Fenway has become. How much of this article is made up?

  • Really badly written.

    2 Replies - Reply Now

    • I think you mean “poorly written.”

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