Knuckling Under to James ‘Whitey’ Bulger and the Winter Hill Gang of Boston!

“Whitey always knew what buttons to push with me, and this time he was pushing the rat button.” Johnny Martorano – Hitman by Howie Carr

Like many people, the capture on June 22nd of Whitey Bulger, the boss of the Winter Hill Gang in Boston, caught my attention. I was reading that Whitey could cause all kinds of problems for the FBI, if he started talking. It was at this point that I realized I was beginning my read of the book on the last page. How stupid of me!

james whitey bulger

I needed to turn back the pages, maybe decades, to the beginning of the story. Well, not all the way back to the beginning. This is not the three parts of The Godfather; you know, the days in Sicily, when Vito Cascio Ferro (Don Vito) goes to New York (in 1901) and creates the American version of La Cosa Nostra.

As a matter of fact, the accounts of James Whitey Bulger is entirely new to me. Okay, so it’s touched on in Martin Scorsese’s comeback film, The Departed. But what is real and what is fiction in the film? Does Jack Nicholson deliver an accurate rendering of Whitey’s character, or does he tend to distort the image of Whitey Bulger?

I knew I wasn’t going to get any easy answers until I buckled down and pursued some relentless research on these rollicking days of Boston’s seediest history. Maybe a history that could best be swept under the rug; but that won’t happen, since the curiosity of the public is as ravenous for Whitey as it was for Big Al or his malicious feat of mob terrorism, the St. Valentine’s Day Massacre.

My beginning was an old fashioned Google search of James Whitey Bulger, which promptly brought forth some promising leads. I scoured the Wikipedia entry and quickly realized I was in for a formidable task of unraveling four or five decades of non-stop vice, violence and corruption of the slimiest, yet provocative-iest caliber.

The image of Jack with that severed hand came back to me at this moment. I’ve encountered some tough reads in the past, such as Wise Guy by Nicholas Pileggi, but maybe I didn’t completely realize what I was about to get myself into.

I suppose Martin, Deniro, Ray, Jack and Joe have had to sort through a lot of this sordid literature, to prepare for their mobster roles, but still it’s hard on an older guy such as myself.

Anyway, I picked up a book, Organized Crime by Paul Lunde at Half Price Books, for just 3 bucks. Encyclopedic in nature, and jam-packed with pictures, I’m using it as a reference to get up to speed on this time be-gone graft – okay, nice biographical sidebars of bad guys and check out the black and white of the Levee district of the South Side of Chicago taken in 1910.

south boston liquor mart

Now if you want Whitey’s rough and tumble days, that begin in the 1950s and go all the way to the present, you guessed it, your primary source should be The Boston Globe, that is a depository for hundreds of articles about Whitey and the Winter Hill Gang.

Fortunately, many of these articles, including some historical summaries, are published on the internet. I will give you a good link at the bottom of my piece.

I got through three of these articles this morning. These are well-written, dating back from the late 1980s and mid 1990s – detailed, fascinating, shocking, well-researched, you name it.

Valuable resources for anyone with half an interest in what was really happening in those days, instead of the usual picture-postcard of the Old North Church, the Charles River, or the cozy city of Cambridge and the Harvard Campus.

I lived in Boston in 1971, went to BU, but I didn’t know all this stuff was going on. By the way, the writers from the Boston Globe are: Gerald O’Neill, Christine Chinlund, Dick Lehr and Kevin Cullin, with Mary Elizabeth Knox as the main researcher.

Here’s some titles: Law enforcement officials’ lament about an elusive foe: Where was Whitey? or New team, tactics hastened Whitey Bulger’s fall or As two brothers begin to flex their muscles, busing enters the picture.

I went by Book People to pick up my prize catch, Hitman – The Untold Story of Johnny Martorano by Howie Carr. Unbelievable! The publisher is Forge – A Tom Doherty Associates Book. Every page is loaded with hijackings, scams of all sorts, or unspeakable gratuitous violence, graphic and grizzly – how could this happen in the U.S. of A.?


Don’t know much about Howie Carr, other than he has a talk show up in Boston and is a veteran columnist for the Boston Herald. I do know, however, he has the made-guy rap down to an fine art! (Phrases like BalloonHead, or Knuckled Under or Flipped or, my favorite, Side-Stepping a Wiretap are technicals for the business!)

Furthermore, I’ve never seen so many mug shots before in my whole life! Every other page has a wise guy snapshot, with the slippery countenances of squeaky-clean model citizens, like Bobby Palladino, or Joe Barboza, or Punchy McLaughlin, or the Hughes brothers, or Hugh “Sonny” Shields, or poor Richie Castucci, whose body was stuffed in a trunk after he was murdered by Johnny Martorano.

I actually read the chapter The Last Hit (pages 330-393) this morning, because I wanted to see for myself how some of Whitey’s contracts were carried out. In that chapter we see how Brian Halloran was eliminated, since he knew too much about the hit on Louie Litif, as well as the World Jai Alai executive, Roger Wheeler, who was killed up in Tulsa. Whitey does this one himself (that is, the Brian Halloran hit, along with a ski-masked confederate), sporting a brown Afro wig and using an automatic carbine, in an old-fashioned drive-by (dating back to the Roaring Twenties, not the Gangland drive-byes of LA from the 1990s).

brian halloran

A shorter version of this convoluted web of corruption and what is known in the business as ‘flipping’ can be had on the Tru TV Crime Library site, aptly titled: James ‘Whitey’ Bulger by Anthony Bruno.

This comes in at just 11 short chapters, and will help you put together a fitting presentation by way of a timeline, since these dark deeds cover nearly half a century of deceit, money laundering, and smoking .38 snub-nosed pistols hidden in a paper sack.

There’s no quick fix on how the FBI gets tangled up with the Irish Mob, or how Whitey was able frame-up the traditional Italian Mafia by using this rat of a rogue, FBI agent Zip Connolly, who’s now a fallen (Fed) of an angel himself.

You have to go back to the very beginning; the Gang Wars in the 1960s, Whitey’s several stretches in prison (including his days as a guinea pig for the CIA, taking LSD), the all important Teddy Deegan hit, that seems to be a key to much of this.

Okay, you just can’t cut any corners! Howie Carr doesn’t cut any corners, Dick Lehr doesn’t, Anthony Bruno doesn’t, and, of course, Whitey doesn’t. Check out all the trouble he goes to when he disappears in 1994.

He had been planning this out for years, how he’d bring it off, precisely how he would do it. And for his hits he covered all his bets so he could never be fingered by the cops. Don’t you want to know how he pulled off all these crimes, and no one could ever touch him?

Better crack the books! Let’s see, I think I’ll order The Brothers Bulger: How they Terrorized and Corrupted Boston for a Quarter Century, by Howie Carr again. You can’t catch a cat, he’s got nine lives and you can’t rat on a rat, he’s got no life at all. Don’t know what that means, but it’s mighty catchy!

Tru TV Crime Library James ‘Whitey’ Bulger

The Boston Globe Archives for Whitey