Sunday, September 20, 2015

Massachusetts Black

James 'Whitey' Bulger has long been a looming figure in popular crime fictions much like Carlos the Jackal  was in the 70s and 80s - a larger than life living legend, romanticized, mythologized and loved to be hated - the subject of numerous true crime books and many more speculative fictions - a stand in boogie man to fit the author's fiendish needs. Real life Keyser Sozes. Until they were captured. When Carlos was apprehended in 1994 and the world got a look at the paunchy terrorist some of the air was let out of the reputation. This was the guy?

When news broke in 2011 that after more than 16 years in the wind Whitey Bulger had been arrested - the era of anything goes Bulger fiction appeared to be over and the new age of reckoning with the devil we knew was going to get messier. Bulger's Winter Hill Gang ruled south Boston for decades, making copious monies from bank robbery, vending machines, drugs, racketeering and uh, jai alai. To further and protect their interests violence, including murder, was employed. But what made Winter Hill, and Bulger in particular, so notable to those who spin stories were three factors:

His brother - William Bulger was a lawyer and eventually a Massachusetts State Senator whose influence was speculated to have been achieved and maintained through a symbiotic relationship with his brother's. This has not been proven, but the suggestion has proven fertile soil for the imagination of writers of fact and fictions.

His accomplice - Special Agent John Connolly of the FBI was a Southie kid who grew up in the shadow of neighborhood big shot Bulger and who became Bulger's handler (though flunkie is the popular portrait). Bulger informed to Connolly on rival criminals, including The Angiulo brothers (and Connolly received a lot of credit in helping to dismantle la Cosa Nostra in Boston), in exchange for tips and protection from prosecution. Through the interference of Connolly on their behalf Bulger's and the Winter Hill gang's operations effectively had free reign with assistance from the federal government.

His disappearance - Tipped off by Connolly of his impending arrest in 1995, Bulger got the fuck outta Dodge and lived in the ether for a decade and a half. With his seeming clean getaway he appeared to have gotten away with everything and he shared a long-term slot on the FBI's Ten Most Wanted List alongside the like of Osama Bin Laden. Who knew what he was up to in the meantime? That's where the fictions really got rich.

One thing was clear - Bulger left a lot of friends and associates holding the bag. Many of them have told their own stories and all "true accounts" should be taken with a mountain of salt, but they do make for interesting reading and, in their corroborations and contradictions, add dimension and color to what will eventually be the accepted definitive history.

Check out

Brutal by Kevin Weeks


Deadly Alliance by Ralf Ranalli


Howie Carr has written several non-fiction books on The Winter Hill Gang's exploits - The Brothers Bulger, Hitman about Johnny Martorano and Rifleman about Steve Flemmi

Dick Lehr and Gerard O'Neill wrote The Underboss about the North Boston mafia as well as Whitey: The Life of America's Most Notorious Mob Boss

Lehr and O'Neill also wrote the book that's just been adapted by Mark Mallouk and Jez Butterworth and directed by Scott Cooper, Black Mass

Whitey - the documentary directed by Joe Berlinger

But... I've got a special affection for the straight-up fictions inspired by the debacle... like -

Pariah by Dave Zeltserman - whew! Blaaackest novel of his Man Out of Prison thematic trilogy. Zeltserman lets his inner psychopath off the leash creating monsters clearly inspired by the Winter Hill cast's exploits and late celebrity. You've been warned.

Martin Scorsese's The Departed was an American remake of the Hong Kong film Infernal Affairs directed by Andrew Lau and Alan Mak, but Jack Nicholson's Frank Costello was screenwriter William Monahan riffing on Whitey's two faces.

Showtime's Brotherhood created by Blake Masters was looking to fill the soon to be appearing gap in pop culture by the final exit of HBO's reigning organized crime family drama The Sopranos and told the story of the Caffee brothers - the younger, Tommy (Jason Clarke), is a politician and the older, Michael (Jason Isaacs), is a gangster who come out of hiding and returns to Providence after the last witness against him turns up dead. The Caffee's resemblance to the brothers Bulger is well...

Brotherhood isn't the only Showtime program to wear its Bulger influence on its sleeve. The first season of Ray Donovan features none other than James Woods playing cold-blooded Boston gangster in hiding Patrick 'Sully' Sullivan who risks blowing his cover by coming out in the daylight to kill Jon Voight. Sully is even traveling with his girlfriend who's driving him crazy on their cross country trip overly-fond of her dog. Bulger's lady on the lam friend Catherine Elizabeth Greig was reportedly an animal lover and authorities speculated that the couple may have been visiting animal shelters wherever the blue hell they were in the world.

With it's Boston locale and cast of criminal losers ratting each other out in exchange for favored treatment from law enforcement it's tempting to throw George V. Higgins' The Friends of Eddie Coyle into the mix here, but its 1970 publication predates the unholy alliance of Bulger and the FBI by a couple of years, so we'll just call it inspired by prophecy (Higgins, as a prosecutor, was perhaps bearing witness to what was a more common occurrence than the official record would have us know).

I haven't read it yet, but Howie Carr is returning to Bulger-land with Killers, a work of fiction that imagines fallout from the scramble to fill the power vacuum left in southie after the downfall of the Winter Hill gang.

The truth is ugly, and the consequences of corruption won't be played out for generations, but the story of what went down in Boston, the black mass, the deal with the devil, is the rich narrative stuff we tell ourselves again and again to explain our own complicity, worst impulses and possible fates.

2 comments:

Dana King said...

I Lived in Massachusetts in the mid-80s, and was aware of William Bulger's reputation as the most powerful man in the Commonwealth, governor be damned. Read Howie Carr's THE BROTHERS BULGER a few years ago and thought it was a bit of a hatchet job as far as James was concerned, until I read BLACK MAS last year, and have read some of the reports that have come out since Whitey's arrest. No one could make shit up that goes beyond what he did. What Bulger and Connelly did rivals any James Ellroy plot. He'll be fodder for crime fiction forever.

jedidiah ayres said...

Ellroy plot - that's an apt description