Whitey's Payback (2 page)

The world is a messy place. Ever since Adam and Eve were chased out of the Garden of Eden, we have known this to be true. It is the job of elected officials, civic leaders, and parents to promote the illusion that life is fair, people are good, and the world is an orderly place; our daily lives at home, school, or on the job are designed to lend credence and support to this illusion.

The journalist’s job is to drag this fantasy out into the light of day, to pull back the curtain and make sense of what seems chaotic and difficult to explain.

I am not attracted to the dark side. I am attracted to the light, and what that light reveals about the true nature of the social universe.

The various articles in this collection were written over a twenty-two-year period. They reflect my interest in crime as a vast ecosystem, a parallel universe to the social and economic system we observe in the upperworld on a daily basis. The way I see it, one cannot exist without the other. In the United States, business, politics, and crime are frequently intertwined. What is happening below the surface shapes the world as we know it. What is presented to the public is occasionally wrapped in bullshit and lies.

For me, these collected articles are all basically about one thing: the pursuit of the American Dream. To the reader, the question is posed: How far would you go to achieve power and prosperity for you and your own? Some people, out of free will, dire circumstances, or temporary insanity, make choices that take them to the wrong side of the law. Chronicling the path of misguided souls and devious minds has become a big part of my calling as a writer.

It is worth noting that the pieces in this anthology were written for a variety of publications, and that I have never been under the employ of a particular magazine or newspaper. My status as a freelance writer, I like to believe, affords me a certain degree of independence. I am not peddling a specific ideology, nor do I represent the views of an established publication like, say,
Esquire
or the
New York Times
. Even though I have written for these periodicals, I have never been urged to adhere to a particular editorial point of view. I have never been pigeonholed in that way. My reporting is my own, and my point of view, when there is a need to assert it, is a consequence of my research and not an editorial dictate from above.

Creatively and spiritually, I am nurtured by the work. And the kind of reporting I enjoy most has to do with traveling to locales that serve as the setting and/or incubation chamber for the kinds of criminal activity I write about.

For a crime journalist, there are few undertakings more invigorating than traveling into a city—say, Kingston, Jamaica, or Hong Kong, or Ciudad Juárez, Mexico—in search of a good story. The trip must be planned with near-surgical precision. If you know what you’re doing, some important interviews will have been set up ahead of time, so that you come into town and hit the ground running. You travel light, dress unobtrusively, carry little more than some research material, a notepad, a tape recorder, a laptop. You stay somewhere downtown in an anonymous hotel, a Holiday Inn or something similar. You circulate without calling attention to yourself, talking with people on all sides of the law, playing dumb, if necessary, to get what you need. You profess to have no ideological agenda, and hopefully you do not, for to tip your hand one way or the other can quickly rile passions and create untenable situations. You get what you need and then get the hell out of town as quickly as possible. Hopefully, the sources you have spoken with think little of your visit until after they see your article in print and react accordingly.

I do not whack people, but I can’t help but think that what I do on these assignments is akin to being a hired assassin. You arrive from out of town as a mysterious stranger. Every move you make, every conversation you have, is geared toward a specific goal. The task at hand is to accomplish what you came for cleanly and professionally, and then—
poof
—disappear in a cloud of smoke.

Seated in the prison visiting room in upstate New York, Mad Dog Sullivan smiles at my analogy. He finds it cute. The idea that a writer’s gathering information and putting words down on paper is in any way similar to the actions of a professional hit man is the kind of literary prestidigitation that brightens his day. Sullivan knows about high-intensity assignments that leave people scratching their heads, wondering what happened. But he also knows that the end result of his line of work is a dead body and shattered lives. “I belong in here,” he says, “no doubt about that. If they were to give me the death penalty, I can’t really argue with that, either, even though I don’t want to die.”

The immorality of Sullivan’s actions is clear, but this does not stop the hit man from taking pride in his work. And this is where Sullivan and I sense a kinship, a mystical connection that can sometimes exist between a writer and his subject, no matter how contrary may be their backgrounds, lives, or daily existence. Sully and I come together out of a shared appreciation of craftsmanship.

Believe it or not, Mad Dog always operated within a personal code. For one thing, he has never been a rat. Many times since he began his most recent period of incarceration in 1981, he has been approached by federal agents and prosecutors offering him some kind of deal if he would testify against organized crime figures for whom he worked. Sullivan’s response has always been the same: “Go fuck yourself.”

The other part of Mad Dog’s code has to do with being the best at what you do.

At one point in our conversation, I ask Sully to describe his cleanest and most professional hit. He described the planning and execution of a particularly perilous assignment with matter-of-fact satisfaction, how he stalked his victim—a notorious underworld figure—until he knew the man’s daily routine. Sully described how he created a disguise and chose a particular caliber weapon best suited to the unique conditions of the shooting. One night, he penetrated the victim’s inner sanctum—his favorite saloon. Joe got right up next to the guy, chatted with him at the bar for twenty minutes before shooting him once in the head, then walking—not running, walking—right out of the bar. His disguise was so seamless, and the act so sudden and unexpected, that witnesses gave three entirely different descriptions of the shooting, and a description of the shooter that guaranteed that Joe Sullivan, without the disguise, would never be identified as a suspect.

Sullivan’s appreciation of a job well done extends to my own undertakings as a writer. Since he’s been in prison so long, Sully has lots of time on his hands, and he’s become a voracious reader. He is fascinated by the process of gathering information and getting it down on the page. He asks me if I use a tape recorder or take notes when I’m doing interviews. “How do you get people to talk to you?” he asks. He wants to know how I’m able to put so much into my writing and still keep everything organized. He’s curious about how I’m able to remain mostly objective when writing about people that many would dismiss as “scumbags.”

I answer Joe’s questions, and he listens attentively to my answers.

I am fascinated by his life’s work, and he is fascinated by mine.

Over a couple of visits to the prison visiting room, we continue our conversation. Often, Mad Dog and I become so engrossed that it’s easy to forget where we are. The hours pass, the day drags on. We are merely two craftsmen—the assassin and the journalist—discussing the tricks of our respective trades.

The sixteen stories in this collection are republished here in their original form. With articles written fifteen and twenty years ago, it is tempting to go back and edit or rewrite from a revisionist perspective, to bend the information to a contemporary point of view. Fortunately, I am not the kind of writer who is obligated to make prognostications or provide “expert opinion” on the likely outcome of elections or sporting events. These articles represent the time in which they were written, snapshots from America’s ongoing crime narrative.

The books I have written are sometimes from a historical perspective, but my journalism, as represented by these pieces, chronicles America’s crime history in real time. To be judged fairly, they must be taken as investigations into an evolving phenomenon, though with the benefit of hindsight they can also—for better or for worse—be evaluated for their accuracy as harbingers of things to come.

The title of this collection—
Whitey’s Payback
—is drawn from the most recent collection of articles dealing with the prosecution of Boston mobster James “Whitey” Bulger. The story of Bulger’s capture and prosecution has many of the characteristics I most relish in a good story, namely, deeply rooted historical underpinnings that help explain a contemporary situation.

Having Mad Dog Sullivan and Whitey Bulger open and close this book has a certain symmetry: Taken together, they represent the last of a kind of old-school gangsterism that most people would rather deny ever played such a monumental role in American urban life.

Over the years, one fact has not changed: In the United States, the narrative remains open-ended. Being a crime journalist is the gift that keeps on giving. When gangsters, con artists, porn kingpins, and corrupt lawmen stop using the American Dream as their license to commit crime, I will stop writing about it. Short of that happening, I hope to see you again in another twenty-two years, with another collection of stories.

Not long after I published my first book, in late 1990, I received a call from an editor at
Playboy
. The editor wanted me to write a feature article for the magazine. No major publication of this stature had ever before called me, out of the blue, with the offer of an assignment. It was a big step in my career as a journalist. The editor told me what they had in mind, though, frankly, I was hardly listening. I accepted the assignment immediately because it felt like an important opportunity. It was only later, after I’d hung up the phone, that it dawned on me what I was being asked to do: The story was to be an exposé on the Witness Protection Program.

Can that even be done?
I asked myself.

It was a good question, one I should have asked myself
before
I accepted the assignment.

The Witness Protection Program was, and remains, a highly covert federal program. It was designed to be secretive, a program that you could not trace or expose.

And so began a pattern for me of taking on certain reporting assignments with considerable fear and trepidation about whether or not that particular undertaking could be accomplished.

The article about the Witness Protection Program took six months of research and went down many blind and frustrating alleyways before appearing in the April 1991 issue of the magazine. The editors at
Playboy
were pleased with the result and quickly came back to me with another assignment. They wanted me to write an article that charted the decline and fall of the Mafia in the United States.

I had little interest in writing about the Mafia. In the early 1990s, I sensed there were many great stories to write about organized crime in America, but the story of the Mafia was old news. Even a story about the decline of the Mafia felt like old news. To me, magazine and newspaper editors were missing out on the most interesting crime phenomenon of our time: the emergence of newer ethnic crime groups that were using gangsterism and organized crime as a process of assimilation much like previous generations of Italians, Irish, and Jews had used crime as a way to carve out their own slice of the American Dream.

I told the editor at
Playboy
that this was what I really wanted to write about. And so we came up with a compromise. I would do a series of three articles that would chronicle this transformation that was taking place in the American underworld. Two of the articles would be about the emergence of a new group, and the last article would be about the decline of the Mafia. The series was entitled “The New Mob” and it ran in the magazine over a nine-month period, from October 1991 to September 1992.

Logistically and as a research assignment, the series was a challenge. It established a method for me that I have tried to continue throughout my career, which is to approach a subject with a wide lens and then zoom in on a particular storyline, to reveal the big picture and then focus on details within the big picture.

To write each of these articles required absorbing a tremendous amount of information, not just about the criminal activity of the subject I was writing about, but also the cultural and political factors that helped shape a particular criminal phenomenon or gang, both in the United States and the country of origin.

There was another proclivity that I established with this series that I have tried to replicate whenever possible, that of traveling, when it is called for, to complicated, challenging locales (in this case, Kingston and Hong Kong) on high-intensity information-gathering assignments.

I am not a gratuitous thrill seeker. I do not bungee-jump or skydive on the weekends. And I do not, per se, take these assignments out of a Hemingwayesque sense of adventure. But I do relish the challenge of going into an environment that is new, a situation that requires street smarts and urban survival skills. I take pride in doing my homework and navigating these environments in a way that minimizes the opportunity for disaster. A successful research trip is one where you penetrate as deeply as possible, get the information you need—maybe even more than you hoped for—and then come home all in one piece, older and wiser and with experiences you remember for the rest of your life.

I have learned that these trips are often filled with fascinating moments that sometimes never make it into the article I am working on.

For instance, on my very first research trip for the
Playboy
series, I found myself in central Kingston, a place I had never been before. If you are not from Kingston, and have never been exposed to extreme Third World poverty, the conditions in the shantytowns and tenement yards are shocking. In 1991, when I was first there, many of the neighborhoods were cordoned off by makeshift barricades. For fifteen years or so, the island had been in the throes of a wave of gang violence touched off primarily by the partisan wars between Jamaica’s two main political parties. Each ghetto neighborhood was aligned with one of the two parties, and the gunplay and general violence, especially around election time, was horrifying.