They called him “Whitey” because of the shock of light blonde hair he had as a kid growing up in South Boston. But he preferred “Jimmy,” the name his parents had given him. He was raised in a tenement and rose to the top of his field.

A younger brother, Billy, was equally successful, although in a different line of work. William Bulger was a lawyer who served as president of the Massachusetts State Senate for eighteen years and later was the president of the University of Massachusetts. His was a blue collar success story. Part of the American dream.

James “Whitey” Bulger’s life was more of a nightmare.

It was, however, even more memorable and significant than his brother’s.

Whitey Bulger was a gangster.

This is like saying that Joe DiMaggio was a baseball player. It’s factual, but there’s a lot more to the story.

Bulger’s life is currently on display in movie theaters across the country. Black Mass, based on a great book of the same name written by two Boston Globe reporters, tells the story of his rise and fall. Johnny Depp, who last worked these cinematic grounds portraying FBI undercover agent Donnie Brasco, nails the role of Whitey, offering a complicated protagonist who is alternately sinister, sincere and amoral.

One character in the movie refers to Bulger as a “professional criminal consultant.” It’s a great description and gets to the heart of the story. Bulger didn’t want to acknowledge that he was a cooperator. Being a “rat” was the lowest form of humanity in the world in which he grew up. So he and the FBI put a different spin on what he was doing. For most of his underworld run—from the mid 1970s until the mid 1990s—Bulger was an FBI informant.

What the Bureau refers to as a “high echelon” snitch.

Bulger, on the other hand, saw his “relationship” with the feds as a mutual cooperation pact. He used the FBI to eliminate his rivals and the FBI shielded him from prosecution. For Whitey, it was a “win-win.”

During the twenty years he fed info to the feds, Bulger was a member and later the leader of the Winter Hill Gang, a Boston-area criminal organization that was involved in gambling, loansharking, extortion, drug dealing and murder.

blackmassmovieposterBulger had his hand in all of that. The book and the movie perfectly capture the game that he played.

The FBI made a deal with the devil, and the devil came out on top. Bulger and his top associate, Steve “The Rifleman” Flemmi, provided the FBI with information about the New England Mafia. The feds, on a crusade to taken down the “Eye-talians,” willingly looked the other way as Bulger expanded his criminal activities. What’s more, the agent supposedly “controlling” Bulger gave him information about other investigations being conducted by the State Police, the Boston Police Department and the DEA, all of whom had Bulger high on their list of criminals who ought to be taken down.

None of those investigations went anywhere. Informants ended up dead. Electronic surveillance proved fruitless. One classic example is the story of a listening device the DEA planted in Bulger’s car in 1985. Whitey was tipped off by the FBI, found the device and ripped it out.

Sheepishly, the DEA sent two agents to recover the equipment which was worth about $20,000. Bulger turned it over with a smile, adding with no small amount of bravado that he didn’t understand what was going on.

“We’re all good guys here,” he told the DEA agents who were trying to gather evidence about a massive cocaine ring he was running. “You’re the good good guys and we’re the bad good guys.”

It’s a funny story. But you’re not likely to get much of a laugh if you tell it to the families of the men and women killed by Bulger while the FBI allowed him to run wild.

The FBI romance with Bulger came at a time when the Bureau was effectively eliminating Cosa Nostra in many major cities. But at what price? A similar scenario played out in New York with Colombo crime family capo Gregory Scarpa, who was also a high echelon informant. During an internecine power struggle, Scarpa’s rivals kept turning up dead. There are those who believe the FBI was feeding Scarpa information that helped him and his faction stay on top in that mob war.

In Philadelphia, less egregious but just as ill-advised, the FBI cut a deal in the late 1990s with then mob boss Ralph Natale. The feds fell in love with the idea of flipping a mob boss. Natale, looking at a possible life sentence for drug dealing, was only too happy to cooperate. Problem was his information and his testimony in a major racketeering trial was full of holes. Natale talked a better game than he played, but the FBI bought into what he was selling.

Like Natale, Bulger used the FBI to his own benefit. Unlike Natale, Bulger was the real deal.

Black Mass, the book and the movie, make that abundantly clear.

The book was written fifteen years ago, long before the Bulger story played out. Whitey, given a heads-up by his FBI agent, went on the run in 1995 just as an indictment charging him with racketeering was about to come down.

The agent, John Connolly, was later convicted of leaking information to Bulger and of second degree murder. He is currently serving a forty-year prison sentence.

Bulger spent sixteen years on the lam but was captured in 2011 living with his girlfriend in a rent-controlled apartment in Santa Monica. Police found weapons and more than $800,000 in cash in the apartment.

In 2013, Bulger was convicted of racketeering charges, including his involvement in eleven murders. He is currently serving a life sentence. At age 86 he will most certainly die in jail.

His story, now wonderfully depicted on film, is an underworld morality play that asks more questions than it can possibly answer.

Dick Lehr and Gerard O’Neill, the Boston Globe reporters, raised those same questions in the introduction to their book. The Globe was the first to break the story of Bulger’s ties to the FBI, ties that the FBI denied for years.

“What if the FBI takes down the informant’s enemies and the informant rises to the top of the underworld?” they wrote in April 2000. “What if the FBI protects the informant by tipping him off to investigations conducted by other police agencies?

“What if murders pile up unsolved? If working folks are threatened and extorted, with no recourse? If a large scale cocaine ring, time and again, eludes investigators? If elaborate government bugging operations, costing taxpayers millions, are leaked and ruined?

“This could never happen, right, a deal between the FBI and a top echelon informant going this bad?

“But it did.”

Cinematically, Black Mass lacks the style and pacing of other gangland classics. It is not as good a movie as The Godfather or Goodfellas. But then what films are?

I would also rank it third behind two other Boston-based mob movies, the 1973 film The Friends of Eddie Coyle and Martin Scorsese’s masterpiece The Departed from 2006 in which Jack Nicholson plays a character based on Whitey Bulger. Among the memorable lines from that film is this description from a State Police sergeant about how other agencies should deal with the FBI:

“My theory is…treat ’em like mushrooms,” said the sergeant, played by Mark Wahlberg. “Feed ’em shit and keep ’em in the dark.”

For too long it was the FBI and Bulger who were keeping everyone else in the dark.

Black Mass brings the story into the light. It is one of Johnny Depp’s finest performances. But it clearly was not the FBI’s finest hour.