The decline and fall of James “Whitey” Bulger
posted at 11:10 am on June 23, 2011 by Jazz Shaw
Whether you know about him from the movie The Departed or from the many documentaries made on his life, James “Whitey” Bulger certainly made a name for himself. Coming from the ranks of abject poverty in post-depression era Boston, Bulger went on to become one of the most notorious of the Irish mobsters in the nation’s history, eventually winding up on the FBI’s most wanted list. And now he’s in custody. (Again)
Legendary Boston crime boss James “Whitey” Bulger, who has been on the run for more than a decade, was arrested Wednesday in Santa Monica, multiple law enforcement sources told The Times…
He was arrested by the FBI inside a building without incident, according to the sources, who asked not to be named because they were not authorized to speak on the matter. The details surrounding his arrest were unclear Wednesday night.
The FBI in Los Angeles declined to comment.
The arrest came as the FBI launched a media campaign in 14 cities to help determine Bulger’s whereabouts.
What made Whitey such a standout figure in the world of crime wasn’t simply the fact that he was from the Irish mobs, rather than the early Jewish and Italian organizations. The Irish mobs were a lot more common than some might think in the early part of the 20th century. It also wasn’t his raw viciousness or the trail of death and wreckage he left in his wake. What really made him fascinating to me was the way he played the FBI for so many years and, in the long run, probably hurt them more than they damaged his crime syndicate.
By the time he was rising through the ranks of gangsters at a young age, Whitey was already in frequent contact with federal agents. His handlers saw in Bulger a terrific opportunity to get first hand information on gang bosses and other criminals, making their lives much easier. Sadly, rather than demonstrating some early streak of remorse or a sense of civic duty, Whitey saw the FBI as a terrific opportunity to get rid of a lot of his competitors and bosses without the risk of him or his boys coming down with a sudden and terminal case of lead poisoning.
Apparently the FBI mishandled their informant badly. According to some reports, they were fully aware that he was continuing a career of killing and racketeering even while he was supposed to be working on the side of the good guys. The more they let this go on, the dirtier the agents in question looked and the less able they became to do anything about him. In some documentaries, Bulger is credited with being the original author of a line later co-opted in many movies: “A guy with a mouth like mine could make a lot of trouble around here.”
It certainly looks like that may have been a factor. He didn’t exactly make himself hard to find in many cases, and yet he wasn’t brought to justice for the later, bigger portion of his criminal career until now. And even today, at the age of 81 and in failing health, I have to think that he probably feels like he got away with murder.









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Never heard of the guy.
Seriously.
Purple Fury on June 23, 2011 at 11:14 AM
I’ve seen a lot of chatter that “The Departed” was actually based on a Japanese trifecta of movies.
Not that I care, just mentioning it.
Bishop on June 23, 2011 at 11:17 AM
I’m still cracking up from your joke in headlines last night.
John the Libertarian on June 23, 2011 at 11:18 AM
I knew where he was all the time, I was just waiting for the reward to increase.
slickwillie2001 on June 23, 2011 at 11:18 AM
That’s a strange statement. Inside a jail?
faraway on June 23, 2011 at 11:20 AM
Kill Whitey!
carbon_footprint on June 23, 2011 at 11:20 AM
Embarrassment. The FBI is almost as inept as our Death Panel Experts will be. And almost as corruptable.
KMC1 on June 23, 2011 at 11:21 AM
My inner 12 year old escaped for just the barest moment and raised some hell, the little shiite.
Bishop on June 23, 2011 at 11:22 AM
I suggest you check into his story, it is fascinating.
His brother, Billy Bulger, was the President of the Massachusetts Senate from 1978-1996.
Democrat, obviously.
I have always wondered what his connections to the Kennedy family are. Nobody gets to that position in Mass Democrat ranks without the blessing of Teddy and Co., right?
What about John F’n Kerry?
The fecal matter may be about to hit the rotary ventilation device.
Brian1972 on June 23, 2011 at 11:23 AM
$2,000,000 and a new life (witness protection for the tipster) goes a long way these days…
Should be an interesting trial…
Khun Joe on June 23, 2011 at 11:24 AM
I only knew about him because I watched the Showtime TV series called “Brotherhood” which I learned was based on him and his brother. It’s a super-violent show (definitely in the mold of “the Sopranos”), but it was quite good.
The dynamic between the brothers, one law abiding, one not so much, was the major theme in that show.
mjk on June 23, 2011 at 11:25 AM
“Whitey” Bulger?
I thought it was Anthony Weiner making a comeback under an alias.
The War Planner on June 23, 2011 at 11:26 AM
And that’s too bad. There’s been a lot of good books written about the brothers Bulger and the major foul-ups by the FBI.
Knucklehead on June 23, 2011 at 11:26 AM
I would love to know Billy’s role in all of this.
Slublog on June 23, 2011 at 11:27 AM
Me too. I’m interested in the Kennedy Clan, and their role in this as well.
There is no way that Billy didn’t help Whitey from his perch in the Mass Senate. No freakin way.
A cunning gangster like that isn’t going to pass up that kind of opportunity.
Brian1972 on June 23, 2011 at 11:31 AM
Whitey also won a million bucks on a scratch ticket. Many think that too was rigged.
The local buzz is the FBI wasn’t going to go after him until all the dirty FBI cronies were dead so they could avoid the backlash.
Jane on June 23, 2011 at 11:31 AM
If I recall from the documentary I saw about this, the New York FBI office began to smell a stink from the Boston FBI office, and started a low key investigation.
When the paid moles in the Boston FBI got wind that the NY office was snooping around how they had handled their “informant”, they tipped off Whitey and he split just before he was going to be picked up.
Brian1972 on June 23, 2011 at 11:36 AM
He’s scum, but I hope he ends his life in witness protection.
flyfisher on June 23, 2011 at 11:39 AM
That would be the Infernal Affairs trilogy out of HK.
So is O’reilly going to be claiming credit for this since he profiled the guy the other day?
rw on June 23, 2011 at 11:42 AM
As wiki tells us:
FYI, I’m sure O’Really will have Howie Carr on his show tonight; he had him on Tuesday night just before this story broke wide open. Howie’s 2006 book, “The Brothers Bulger”, is a must-read for those interested in MA political corruption.
Del Dolemonte on June 23, 2011 at 11:43 AM
Whitey is a fascinating story and if the true story of this guy is every known it probably would make Chicago politics look angelic.
ORconservative on June 23, 2011 at 11:45 AM
This goes back to daddy Joe Kennedy.
Here’s a good book about it.
The Brothers Bulger: How They Terrorized and Corrupted Boston for a Quarter Century
And a new one.
Citizen Somerville: Growing up with the Winter Hill Gang [
Knucklehead on June 23, 2011 at 11:47 AM
So is O’reilly going to be claiming credit for this since he profiled the guy the other day?
rw on June 23, 2011 at 11:42 AM
I’d bet money on it. BOR claims credit for everything.
ORconservative on June 23, 2011 at 11:47 AM
I’m not a huge fan of Mitt Romney, but I agree with this article at Commentary – Romney’s campaign to bring down Billy Bulger was really one of the better things he’s done.
Slublog on June 23, 2011 at 11:50 AM
You can listen to Howie Carr (the author of the Brother’s Bulger) here. The show starts at 3:00. He will be all over it.
Jane on June 23, 2011 at 11:53 AM
Meanwhile GM, Chrysler, and Barry and the Crew count the stacks of your money.
Limerick on June 23, 2011 at 11:56 AM
I’m guessing a hospital.
Fallon on June 23, 2011 at 11:56 AM
Oh how we so need a video clip of Obama being asked to comment on this and him coming back with something like “Well, we finally put Whitey down!”
pilamaye on June 23, 2011 at 11:57 AM
Thanks for the info.
Brian1972 on June 23, 2011 at 12:00 PM
Yup, daughter is a film buff but the character that Jack Nicholson played was based on “Whitey”.
So, everybody’s right.
Fallon on June 23, 2011 at 12:00 PM
The Brothers Bulger is a must read, even if you aren’t from Boston.
Howie Carr’s encyclopedic knowledge of the Boston underworld and it’s many ties to politics is legendary. He’s a throwback to old style journalism.
turfmann on June 23, 2011 at 12:08 PM
That’s 3 PM EDT.
Not sure if Howie is there this week; he had a substitute host yesterday. Don’t think he’s on vacation, as he was on O’Really Tuesday night.
Even when Howie’s not there, one of his regular guest hosts is well worth a listen; that would be Col. David Hunt, who’s frequently on Fox News as a military analyst. He and Howie are great pals because they’re both from Maine.
Del Dolemonte on June 23, 2011 at 12:10 PM
He’s also had a legendary feud with Mike Barnicle, now with MSDNC but formerly with Howie’s Boston newspaper competitor, the Boston Glob.
Del Dolemonte on June 23, 2011 at 12:16 PM
He’s there. He was absent for a couple of hours Tuesday to tape O’Reilly, and he was at least there for some of the show yesterday because I heard him.
Jane on June 23, 2011 at 12:18 PM
I had no idea that was the same Howie Carr that wrote the book.
And if you’re into reading about mobster’s here’s another good one written by Henry Hills kids.
On the Run: A Mafia Childhood
If you liked the movie Goodfella’s, this book is the rest of the story.
Knucklehead on June 23, 2011 at 12:21 PM
Our domestic counterintelligence operations are, and always have been, run by the ghastly careerist hacks at the FBI. These are the cretins that allowed the atomic secrets of the Manhattan Project to be deeply penetrated by the Soviets over 65 years ago, and the little pervert Hoover never had to answer for that, did he? No, the dye is cast and we are stuck with the FBI counterintelligence pinheads and their continuing appalling failures such as 9/11. However, there is now reason to rejoice, as the law enforcement side of the FBI has finally caught up with the dying, 81 year old Irish gangster Whitey Bulger, whom the corrupt Boston FBI Office protected for over 25 years. I am sure the jailed Boston FBI agents are pleased with the arrest which, we are told, took place in a “building” (probably a hospital). For this, Washington is considering extending appointment of the current FBI director, beyond the laws of appointment? No “corporate memory” of Hoover, eh?
John Adams on June 23, 2011 at 12:51 PM
No problem, there’s a higher court (a much higher court) awaiting him.
Mojave Mark on June 23, 2011 at 1:11 PM
Compared to Obama this guy is St Patrick himself. The Boston Irish might think they’re tough but the NY Irish could teach them a few lessons. Westies gang leader Mickey Featherstone once walked into a bar in New York’s Hell’s Kitchen with a rival’s head in a hat box. This is a TRUE story.
MaiDee on June 23, 2011 at 1:12 PM
Howie Carr. local talk radio and Boston Herald writer has been after bolger forever. Jokes, sightings, etc. Howie is a good guy,real conservative and also jumps on all the MA corrupt pols. I love him.
retiredeagle on June 23, 2011 at 1:23 PM
The problem for the Westies, as shown by your example, is that they were flat-out, bat sh*te crazy. They were totally out of control with everybody. Craziness like theirs can’t survive, even in the mobster world.
NavyMustang on June 23, 2011 at 1:40 PM
Here is MSNBC’s Mike Barnicle from an Aug 1991 column on Whitey winning the lottery:
In a blatant display of prejudice against local Irish gangsters, some narrow-minded bigots are hinting the Lottery was rigged simply because a friend of Jimmy Bulger’s won $14 million and split the lucky ticket four ways. Next, in a gross display of piling on, the state treasurer, Joe Malone, said he was disturbed that the guy who sold the winning numbers, my pal, Kevin Weeks, showed up at Lottery headquarters “with a reputed mobster,” and I think he meant Bulger.
First things first: If the Mass Millions could be bagged, I would today be sitting on my fat arse doing next to nothing because my longtime, close personal friend — the former Treasurer and Receiver General of the Commonwealth, Robert Quentin Crane of Presentation Parish — and I would absolutely have found a way to send the money South. And don’t think I didn’t inquire.
Whitey Bulger, Kevin Weeks and the two Linskey brothers won it on the up and up. Hey, good things happen to good people, right? Of course, there is an army of malcontents who refuse to believe that the result of a mere game of chance is on the level when the cash cow moos at the doorstep of a man — Bulger — who, according to illegal eavesdropping by FBI agents and their cheap equipment (And I will show you how lousy their stuff is), runs a vastly overrated criminal enterprise in the area. Naturally, this paranoid bitterness is fueled by the fact that Jimmy’s brother runs the State Senate, although the one man has nothing more to do with the other than saying, “Pass the gravy,” during occasional Sunday dinners. But, with all the publicity, the Lottery has become part of local gangster legend.
The myth took root decades ago after Jimmy returned home from away games in Atlanta, Alcatraz and Leavenworth, where he earned his federal letter sweater. Then, Southie was sort of dominated by nickel and dime hoodlums claiming to be part of the Mullen Gang. This was the only gang in America that took its name from a street sign. They were supposed to be bad but, bottom line, they were stupid and Whitey is not.
He aligned himself with a larger outfit, many of whose members were of Mediterranean extraction and thus easily tricked by glib Irish wit. His associates loved to talk with their mouths full of linguine and clam sauce and, in between twirling noodles onto spoons, they talked themselves into jail or the trunks of Lincoln Town cars.
Some Irish were wounded, too. Among them was a Bulger acquaintance, Buddy Roache, the police commissioner’s brother, who got shot in the spine and must now rely on a wheelchair for movement. Then, there was the commissioner’s former brother-in-law, Mickey Dwyer, who got in a fight with the late Donald Killeen, one of Whitey’s executive vice presidents before they changed the title to executed vice president. Donny bit Mickey’s nose off in a fight but, out of friendship, called a cab after the beef and had the nose sent to the hospital. The cabbie got a tip, but the surgical procedure failed and to this day Mickey sounds like a cold front out of Canada.
There was Billy O’Sullivan of Savin Hill, who did not know enough to stay within his own zip code. Billy had more hits to his credit than Elvis but he got greedy. They found his car in Charlestown with Billy’s shoes alongside the spare tire. And that’s all they ever found.
Louie Litoff was another part-time member of Jimmy Bulger’s cabinet, a bookmaker with a hundred different jogging outfits. On his last run around the block, Louie stepped on Red Assad’s foot outside the Waltham Street Cafe. It’s the little things that are important and soon Louie had a new nickname and a new address. He went out being called, “Bowling Ball Head” due to the three bullet holes in the back of his skull, and he now gets his mail at Mt. Calvary Cemetery.
Believe me, it’s not all ice cream and sweet dreams for Jimmy Bulger. Someone is always after his behind or his job. He’s always the object of some hostile takeover.
Just last week, a moron in the D Street project who either did not know or, worse, did not care whom he was fighting with took a couple of swings at Jimmy. This was hours after Kevin Weeks’ brother-in-law got beaten and robbed there. Before that, two women stopped at The Busy Bee in Brookline for coffee, grabbed some napkins and came up with an electronic device they figured for a bomb. See, Bulger once went to the restaurant, so “The G’s” wired it with one of their ridiculous machines. If the FBI had run the war with Iraq, we’d be swearing allegiance to Saddam Hussein this morning.
So, lay off Jimmy Bulger. For the first time in his life, he got lucky, legitimately, and won the lottery. Knowing him, he probably already has handed out money to St. Augustine’s, figuring that when he goes — and the odds on that are better than winning Mass Millions — there will be some people left behind who will say, “Not a bad guy.”
Rich on June 23, 2011 at 2:19 PM
Now the funny part is that Whitey never won the lottery. Someone in Southie did and Whitey tracked them down and bought ticket. Then he and his crime partner came forward and cashed the ticket and then had a legitimate income.
Rich on June 23, 2011 at 2:20 PM
I imagine Howie Carr is as suprised as anyone Bulger was found in Santa Monica. On BOR he was convinced the guy was out of the country and couldn’t get back to the U.S if he wanted too. He convinced me.
I do hope Whitey rats on the connected MA politicians. No doubt the Kennedy’s are in his league.
Buttercup on June 23, 2011 at 2:39 PM
oops “to” not “too”. I’m at work and have limited HA time. I read lots, type little and proofread even less.
Buttercup on June 23, 2011 at 2:50 PM
“How Sweet It Is!”
~Howie Carr, a few seconds ago.
Del Dolemonte on June 23, 2011 at 3:08 PM
The odious Mike Barnicle, former plagiarist columnist of the Boston Globe.
The true extent of how Whitey and Billy worked in tangent to become a powerful force in Massachusetts politics will never be known.
Senate President Billy was able to gain a stranglehold on political power due to his gangster brother’s intimidation. Billy made sure law enforcement was hobbled for many years. A despicable pair.
vilebody on June 23, 2011 at 4:02 PM
LOL, Channel 5 in Boston just reported that they got a peek at Whitey’s booking photo. He’s wearing glasses and has a full beard and moustache.
The reporter said he was “grinning like a Cheshire Cat”.
Del Dolemonte on June 23, 2011 at 4:48 PM
Dang! I missed Howie’s show today. Of all days, too! This was Howie’s cause celebre.
/Mr Lynn
MrLynn on June 23, 2011 at 11:14 PM