Whitey Bulger Beats the System Again

Calling him “a little sociopath” and insisting that he was not, in fact, “a face of the city” of Boston had the opposite of its intended effect.

The reality of James "Whitey" Bulger, now sentenced to two life terms, can't possibly compete with the myth. That was all too clear from the remarks addressed to him at sentencing by the prosecutor and the judge, each in a different way speaking on behalf of the public.

Calling him "a little sociopath" and insisting that he was not, in fact, "a face of the city" of Boston had the opposite of its intended effect. Instead of reducing the defendant's status, it reaffirmed that Bulger's legend, augmented and transformed by film and television, will live on long after the man himself has faded.

From the beginning of the trial, the prosecution team seemed less focused on getting a conviction -- essentially assured by the facts -- than by making some sort of civic point. Bulger had been romanticized, described as the inspiration for Jack Nicholson's character in "The Departed" (never mind that the movie is actually the remake of a Hong Kong gangster picture that had nothing to do with Boston). His legendary status as a kind of benign-but-brutal master criminal, closely connected to politics through his brother and magically able to elude capture, seemed to drive the prosecution over the edge.

The government wanted this image crushed because it imagined that the idealized picture of the appealing criminal threatened the values of law and order. This of course was preposterous. I can think "The Godfather" is the greatest American film of the last half-century (except maybe "Godfather II") without feeling the least bit of sympathy for the Italian mafia as it once existed. HBO lives and flourishes because its writers understand that, from Tony Soprano to Stringer Bell of "The Wire" to Tyrion Lanister of "Game of Thrones," we love a complex antihero. But fans of these series are about as likely to sympathize with actual organized crime kingpins as they are to invade a fantasy kingdom with dragons.

The government also wanted to debunk the Bulger myth because at least some of it was grounded in the truth. Whitey was in fact deeply enmeshed with the police and Federal Bureau of Investigation, who took his bribes, thought they were playing him, and enabled him to escape and stay hidden for so long. The trial epically failed to make this bizarre and fascinating set of facts go away. In fact it completely ignored the issue, leaving us no wiser about which officials were on the take than we were when we started.

Against this backdrop, the prosecution at sentencing could do little more than insult the defendant ineffectual, symbolic terms. Federal prosecutor Brian Kelly called Bulger "a disgrace to the Irish," which may or may not be true but is not technically a crime, at least not anywhere outside Boston. Bulger may be a "sociopath" -- the term has no meaningful scientific content, so why not? -- but Kelly called him a "little" one, as though his diminutive size were relevant to his crimes.

Judge Denise Casper, for her part, found herself struggling with Bulger's image. In open court she told Bulger, "You have over time and in certain quarters become a face of this city," a claim that is probably not true at all but certainly would make Bulger happy if it were. Having introduced this vast overstatement of Bulger's importance, the judge was able to do no more than tell him, "You, sir, do not represent this city." Really? I thought she just said he did?

Worse, the judge actually said while sentencing Bulger that "at times during the trial, I wished that we were watching a movie . . . but . . . it was not a movie." This stunning admission showed that a sitting federal judge, nominated by the president and confirmed by the Senate, was no different than the rest of us: her fantasy of the trial was cinematic. She wished to be watching the mythic, movie version of Bulger, not the comparatively dull reality.

The victims' families are real, and it is not surprising that, when they addressed Bulger in court, they sounded exactly like the families of victims of any other murders. Unlike the judge in the prosecution, they were not interested in all in Bulger's image. They weren't self-congratulatory actors in a government-funded drama, just human beings who had lost loved ones.

But the trial judge's closing salvo tells you all you need to know about the future of the Bulger myth: it will live long and prosper on the screen. The new Showtime drama "Ray Donovan," which quite literally brings Boston gangsters to Hollywood to meet the stars (what an easy pitch that must have been), probably owes its existence to Bulger's notoriety.

About halfway through the first season, the show introduced a character based directly on Bulger, the creatively named Patrick "Sully" Sullivan, played by James Woods, to resolve the convoluted plot difficulties into which the show runners had led the season. Woods, following the example of the series' lead actor, Liev Schreiber, played the character as a man without affect: the sociopath without charm, who kills for convenience and without pleasure -- and who visits his mother weekly (in Boston!) without fear of being apprehended.

Truth to be told, Sully Sullivan wasn't much of a character. But he effectively symbolized the idea of a criminal who couldn't be stopped except by death. In that, art imitated life that will be in turn imitated by art: James Bulger will die in prison, but Whitey Bulger won't.

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