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The Secret Life of Whitey Bulger
  • June 26, 2014 : 13:06
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The FBI was forced to admit Bulger and Flemmi had been informants. But the prosecutors and Department of Justice higher-ups were loath to acknowledge that as TEs they had been given immunity from prosecution in exchange for their intelligence. Connolly refused to play along, and as a result he became the DOJ’s whipping boy, its scapegoat.

By October 2000 Connolly had been charged with nine counts of criminal action, including racketeering, obstruction of justice and making false statements to law enforcement officials. Essentially the government prosecutors attempted to prove that instead of merely handling his Winter Hill informants, Connolly had joined Bulger as an active member of his gang. The trial had the city of Boston riveted. Connolly was found guilty of racketeering, obstruction of justice and making false statements. Bulger was gone, and the feds needed to save face. Using testimony from a Winter Hill gang insider (testimony that was later discounted by another witness), a jury found Connolly guilty of tipping off Bulger to the impending indictments so he could flee before the law came for him. The judge sentenced Connolly to 10 years in federal prison.

Seven years later, Connolly was wrapping up his federal bid when he was charged in Miami with conspiring with Bulger and others to murder a shady Boston businessman named John Callahan. The former president of World Jai Alai, Callahan was involved in a scam with Bulger—until he was found riddled with bullet holes at the Miami airport in the trunk of his Cadillac. The charge claimed that Connolly had tipped Bulger off that Callahan was going to drop a dime on him for the murder of World Jai Alai owner Roger Wheeler. Callahan’s body had been found with one dime facing up on his chest. Connolly was transferred from the federal prison in Butner, North Carolina to the Turner Guilford Knight Correctional Center in Dade County, Florida. He was held in the hole on 24-hour-a-day lockdown.

At the Miami trial, prosecutors trotted out a rogues’ gallery of hit men and snitches to testify; it was in all of their best interest to take Connolly down. Connolly’s former supervisor John Morris again took the stand and wept through his testimony. Although he admitted to accepting thousands in cash and a case of fine wine from Bulger (Bulger called him Vino for his fancy palate), Morris testified against his underling Connolly and walked without ever spending a minute behind bars. Hit man turned government witness John Martorano—who admitted to committing the murder and placing the dime on the victim’s chest after shoving the body into the trunk of the Cadillac—testified against Connolly. Today Martorano, known as the Basin Street Butcher and with more than 20 confirmed notches in his belt, is a free man often seen dining in fine Boston restaurants. Another admitted murderer who testified against Connolly in exchange for a lesser prison sentence is Bulger’s partner Flemmi.

Connolly was convicted of second-degree homicide with a firearm and sentenced to 40 years in prison—a virtual life sentence. His Miami lawyers belatedly pointed out that in cases involving the crime for which he was convicted—second-degree murder with a firearm—Florida statute requires that it be proved beyond a reasonable doubt that the firearm used in the murder was in the personal possession of the defendant during the commission of the felony. That element of the crime was never proven; in fact it was never even alluded to in the state’s case. The only firearm in Connolly’s possession would have been his FBI-issued weapon, which was with him in Massachusetts, hundreds of miles from the scene of the crime.

The trial judge agreed with Connolly’s attorneys that the jury’s verdict, and therefore Connolly’s conviction, was flawed. But, he pointed out, the lawyers had filed their motion for arrest of judgment several days beyond the 10-day period allowed by law. Because the motion had not been filed in a timely manner, the judge ruled that the conviction and 40-year sentence would stand. And the appellate court in Miami denied the appeal without issuing an opinion. 

As Connolly watched his life slip away in a Florida prison, FBI agents maintained their command center in Boston and spent millions on one of the most elaborate and expensive criminal manhunts ever mounted. All the while, Whitey Bulger and his lady, Catherine Greig, were living quietly in Santa Monica, hiding in plain sight.

On the eve of the Bulger trial, it seemed a worthy endeavor to travel to Boston to interview some of the people who had been closest to him back in the day when he was assuming control of the underworld and conniving with FBI agents.

Theresa Stanley was in a relationship with Bulger for 30 years. She was on a road trip around the country with Bulger in January 1995 when they heard the news on the car radio that Flemmi had been arrested. In her early 70s, Stanley sat for an interview over lunch at Legal Sea Foods. A delicate woman still mourning the drug-overdose death of her son—a son Bulger had helped raise (“Jim was very strict,” she remembered of Bulger’s parenting skills)—Stanley was also still suffering from Bulger’s betrayal: All the while he was with her, he had two other mistresses, Catherine Greig and longtime girlfriend Lindsey Cyr, with whom he had a child, a boy named Douglas.

“It’s hard to understand,” she said over a bowl of lobster bisque. “I don’t know how a man can live so many different lives and keep up so many lies. It must not be easy.”

Reminded that Bulger, given his dual role as informer and mobster, was adept at living multiple realities, Stanley gained little solace. She had resisted telling her story because the whole thing brought up too many unhappy memories. She agreed to meet only after her son-in-law Chris “Knuckles” Nilan, a former enforcer for the Montreal Canadiens hockey team and a Bulger confidant, had put in a good word.

Stanley confirmed that Bulger had planned for his flight long before he learned of the indictments and Flemmi’s arrest. “He was traveling under his own name while we were together,” she recalled. “But he was aware something was going on back in Boston.”

Once they heard about Flemmi and the warrant for Bulger’s arrest, Stanley said, Bulger immediately stopped using his real name and assumed the identity of Thomas F. Baxter, who had died in January 1979. In 1990 Bulger had obtained a driver’s license in Baxter’s name and had renewed the license again in 1994, a year before he went on the lam.

“Connolly never tipped Jim,” Stanley said. “We weren’t even in Boston at the time. Jim heard the news on the car radio. It’s not right what was done to Connolly. Jim should clear Connolly. He should do that. He should do one good thing before he dies.” Stanley succumbed to lung cancer and died just months after our interview.

It is well established that Bulger had already planned his flight and left town by the time the Boston indictments were unsealed. He had phony IDs and cash at the ready. Connolly had retired from the FBI four years before the indictments. As another Connolly supporter, former FBI agent Joe Pistone, known as Donnie Brasco while working undercover for the FBI, explains, “No one is calling a retired agent to tell him they have an indictment against one of his former informants. It ain’t happening. They keep that information close to the vest.”

Pistone knew Connolly when they were both on the job. “All John Connolly did was his job, what he was hired and sworn to do,” Pistone says.

Hockey player Nilan believes that in addition to clearing Connolly, Bulger wants to set the record straight on several of the killings attributed to him. “Jimmy said to me, ‘The last guy to come in always gets blamed for everything,’” Nilan says. In particular, Nilan and others close to Bulger believe that Flemmi’s testimony against Connolly was self-serving in the extreme, that he lied about several murders Bulger supposedly committed, that he heaped the blame for killing two of Flemmi’s ex-girlfriends on Bulger and that government prosecutors knew Flemmi lied and therefore committed perjury.

“Jimmy’s very smart,” Nilan says. “I’m sure he’s still got a few cards he can play. Believe me, they don’t want to hear what he has to say.”

Lindsey Cyr—mother of Bulger’s only child, Douglas, who died of complications from Reye’s syndrome when he was six years old—has stories of Bulger few except those closest to him ever knew. Cyr met Bulger when she was 19 and had a second job as a waitress in a restaurant Bulger frequented while he was working for a construction company soon after his release from prison.

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read more: entertainment, News, issue december 2012


  • Anonymous
    John should not only be exonerated by whitey Bulger but also by the entire justice departments !! Great article
  • Anonymous
    I enjoyed the article but as a friend of "a young US Marshall zeroed in on the lead" I find it odd that Playboy didn't mention his name. Neil Sullivan was THE reason that Whitey Bulger was captured. The FBI was secondary to Neils' relentless work to apprehend a fugitive and his work should be noted.