How The NHL Fit Into Whitey Bulger's Underworld Empire

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James "Whitey" Bulger, formerly one of the country's most wanted fugitives, was convicted this afternoon by a Boston jury on multiple counts of racketeering and conspiracy in connection with 11 gangland-style murders dating back to the 1970s. He will likely spend the rest of his life in prison. But his organized crime activity had a couple of sports connections, specifically with the NHL, the Montreal Canadiens, and the Boston Bruins.

Bulger, 83, operated with impunity for many years as the leader of South Boston's Winter Hill Gang, mostly because his corrupt handlers in the FBI—for whom he was an informant—protected him. In 1995, after an FBI agent alerted him to his pending indictment, Bulger went on the lam. He eluded capture for 16 years until he was finally apprehended in June 2011 outside his apartment in Santa Monica, Calif. Among the items seized when Bulger was captured was a Stanley Cup ring, which prosecutors agreed would not be subject to criminal forfeiture, according to court documents made public this morning, just before the jury rendered its verdict. Bulger has said the ring—which could still be turned over to satisfy a possible civil judgment—was a gift "from a third party." But who could that have been? It's not known for certain, but there's one obvious connection.

One of Bulger's longtime girlfriends, the late Teresa Stanley, had a daughter named Karen who married former NHL enforcer Chris Nilan back in the 1980s, when Nilan was playing for the Montreal Canadiens. Nilan and Karen Stanley are now divorced. This is from Whitey Bulger: America's Most Wanted Gangster and the Manhunt that Brought Him to Justice, the book written earlier this year Kevin Cullen and Shelley Murphy, two Boston Globe reporters who have covered Bulger's activities for years:

He treated her children as his own, even walking Stanley’s daughter Karen down the aisle and paying for her lavish wedding to professional hockey player Chris Nilan—a man famous for his on-ice brawling. Whitey took a shine to his surrogate son-in-law. He had never been much of a sports fan, but when Nilan played for the Montreal Canadiens, Whitey frequently traveled to Montreal with Stanley to attend games. After the Canadiens won the Stanley Cup in 1986, a smiling Whitey proudly posed for a photo with Nilan and the Cup.


That photo, which has been bouncing around the internet for a few weeks now, can be seen above.

But there was another, more direct way in which Bulger used the NHL for his illicit activity. In 1984, Bulger and his associates attempted to smuggle weapons by boat across the Atlantic Ocean to the Provisional Irish Republican Army, with whom they had sympathies in the IRA's long-running battle against British rule in Northern Ireland. The plan was eventually thwarted before the weapons reached their destination, but there was a major problem that had to be overcome to establish the operation in the first place: Joe Cahill, a Provisional IRA founder who was Bulger's connection to the group, was barred from entering the U.S. because he had been convicted of killing a cop back in Belfast. So Bulger and his crew had to get creative to arrange their secret meetings with him. The Boston Bruins unwittingly provided the perfect cover.

From the book:

Joe Cahill was accustomed to doing business in barrooms, but his haunts were usually in his native West Belfast, not South Boston.

Still, there was a war on, and Joe Cahill would go anywhere to get weapons for the Irish Republican Army. So there he was, in the private room on the second floor of Triple O’s, Whitey Bulger’s redoubt on West Broadway. Cahill nodded approvingly at the Irish tricolor strung across the bare brick wall. There was a TV propped up on the bar, and Cahill pulled a videocassette out of a shopping bag.

His short stature, thick eyeglasses, and retiring, grandfatherly manner belied a certain ruthlessness that fit in with the men grouped around him at Triple O’s. There was Whitey, whose reputation preceded him. There was Pat Nee, the Irish-born Mullen gang survivor who had gone from hunting Whitey to hunting others with him. And there was Joe Murray, Whitey’s newest associate, the biggest marijuana trafficker in town.

They were mere racketeers; Joe Cahill was a revolutionary. He was also a legend.

When he was twenty-two, Cahill had been convicted of killing a policeman in Belfast during one of the IRA’s short-lived campaigns of violence in the 1940s. Cahill and his three friends were sentenced to death. His friend and co-conspirator, Tom Williams, was hanged. But the Vatican intervened, asking the British government to spare the other three Catholics facing the hangman. The British would come to regret the mercy they showed Joe Cahill, first in sparing him the noose, then in releasing him after just eight years in prison.

Cahill continued to fight in the IRA’s sporadic, quixotic uprisings. He resigned from the organization briefly in the 1960s, accusing its leaders of going soft and focusing too much on the far-left ideology that was spreading across Europe. He believed that they weren’t concentrating enough on their own immediate struggle. His warnings proved prophetic. When marauding bands of Protestant thugs tore through Catholic neighborhoods in Belfast in 1968, the IRA was impotent, its small, pathetic cache of rusty guns useless at stopping a pogrom. Some took to daubing walls in West Belfast with the taunting slogan “IRA—I Ran Away.” Cahill rose from that humiliation, pushed the politicos aside, and reasserted the muscular tradition of physical-force republicanism. He became one of the founders of a new, more aggressive reincarnation of the republican movement’s military wing, the Provisional IRA.

In the early 1970s, as the IRA took the fight to the British, Cahill went looking for weapons abroad. In 1973, he was captured off the coast of Ireland on a ship loaded down with five tons of guns and explosives, a gift from the Libyan leader Muammar Gaddafi, who hated the British almost as much as Cahill did. When the judge who heard the case described Cahill as the ringleader of the gunrunning scheme, Cahill stood, bowed gallantly toward the judge and said, “You do me an honor.”

Cahill served three years in prison. As soon as he was released, he again began looking abroad for weapons, and it was inevitable that his quest would take him to Boston. In the working-class enclaves of South Boston and Charlestown, it was common to see pro-IRA graffiti painted on the walls. In Southie, a liquor store owner had a huge mural painted on the side of his West Broadway storefront, proclaiming, “Ireland Unfree Will Never Be at Peace.” It remains there to this day. A mechanic painted a towering mural over the entrance to his Lower End garage with the words “Óglaigh na hÉireann,” which meant nothing to most passersby but which was appreciated by Joe Cahill: It means “Irish volunteers” and is what the IRA calls itself in Gaelic, the Irish language. In other neighborhoods, expressing solidarity with an outlawed group would be considered strange, even scandalous. In Southie, it was good for business.

Cahill noticed. “When they drove me around Southie, it reminded me of West Belfast,” he said.

It was common for hats to be passed around the myriad Southie barrooms, collecting for a relief fund for the families of IRA prisoners. Some bars also had permanent jars for donations to NORAID. The debates over where the money went were irrelevant: Even if it didn’t go directly to buying weapons—and there was considerable evidence that some of it did just that—it went to prisoners’ dependents, allowing the IRA to spend its funds elsewhere.

One of NORAID’s leaders, John Hurley, had survived the Charlestown-Somerville gang wars to become a Winter Hill Gang associate, but he spent most of his time raising money, and finding guns, for the IRA. It was Hurley who told Whitey in 1982 where he could corner and murder Brian Halloran, the Winter Hill leg breaker who shopped Whitey and Steve Flemmi to the FBI. And it was Hurley who urged Joe Cahill to meet with Whitey Bulger. Hurley knew that if Boston’s Irish criminals were going to coalesce to help the IRA, Whitey had to sign off or it wouldn’t happen. Whitey had contributed to NORAID regularly, taking the money from his gang’s expense fund, but he styled himself more than just a barstool patriot—he styled himself Irish. He obtained Irish citizenship through his maternal grandmother, Jane O’Brien McCarthy, who was born in Cork City in 1866. Whitey acquired his Irish passport in 1987. Beyond its sentimental value, he knew that the passport would be an asset if he had to go on the run.

But while Whitey always supported the IRA, it was Joe Cahill’s visit to the Triple O’s that dramatically escalated his involvement. Whitey idolized few people, but Joe Cahill was one.9 And when Cahill insisted on going to South Boston to meet him, Whitey was flattered. “Jimmy really looked up to Joe Cahill,” said Kevin Weeks. “Cahill was a legend.”

As a convicted killer and gunrunner, Joe Cahill was barred from entering the United States. But he was not barred from entering Canada, and the Boston gangsters perfected a scam for sneaking him across the border. The IRA was told to send Cahill to Canada during the winter, so that the trips coincided with when the Boston Bruins hockey team was playing the Canadiens in Montreal. IRA sympathizers in Charlestown and Southie then chartered a bus to bring Bruins fans to the games. Cahill usually traveled with three companions, so four Boston hockey fans were induced to stay a few extra days in Canada; Cahill and his traveling party took their place on the bus. Border inspections were perfunctory at the time; as long as the number of heads on the bus heading south was the same as the number that had been counted heading north, the men were waved through the checkpoint. On four different occasions, Joe Cahill was smuggled into the United States this way.


Excerpted from Whitey Bulger: America’s Most Wanted Gangster and the Manhunt that Brought Him to Justice by Kevin Cullen and Shelley Murphy. Copyright © 2013 by Globe Newspaper Company, Inc. With permission of the publisher, W.W. Norton & Company, Inc.