There weren't many things that could scare James “Whitey” Bulger, notorious killer and one of the FBI’s "Most Wanted", but when his son, Douglas Glenn Cyr, went missing from a park in Boston, the young boy managed to scare him in a way no other crime gang could. “Jimmy walked up and put his arms around me from behind and whispered in my ear, ‘Somebody dies for this,’ said Lindsey Cyr, Glenn Douglas's mother who revealed in 2010 her 12-year relationship with the legendary criminal.

“From the minute I told him I was pregnant, that was what he had been concerned about," Cyr, a resident of Weymouth, Massachusetts, continued. Luckily, the police found the boy a couple of hours later.

For over a decade, Cyr was Bulger’s lover and mother to his child, Douglas Glenn Cyr. Constantly on the run from rival criminals and the authorities, Bulger went to great lengths to hide his son.

Whitey Bulger is the former leader of the Winter Hill Gang, an Irish-American crime family based in Boston, Massachusetts. After evading the police for 16 years - for twelve of which he was on the FBI's Top Ten Most Wanted List - Bulger was finally apprehended in California in 2011. In 2013, he received two life sentences and five years for his crimes which included complicity in eleven murders.

“He used to say there were four people he’d turn up at a street corner for; Douglas, me, his brother Billy [William Michael Bulger, the former Massachusetts Senate President] or his mother. And we all made him vulnerable,” Cyr told the Boston Globe in 2010.

In 1966, Cyr met Bulger at a café and fell for him instantly. She said, “He was gorgeous. There wasn’t anything not to be attracted to. He was blond, blue-eyed, very well built and handsome.”

Cyr said that Bulger was a perfect gentleman and made her feel safe. As their relationship progressed, Bulger confessed his criminal involvement to Cyr.

“He told me that he had been in jail and that he had done nine-and-a-half years on a 20-year bit, and he had 11 years of federal parole to do.

“I was just blown away. You’re sitting there looking at someone you consider to be a real gentleman and a very nice person and he’s got a history that is bizarre,” continued Cyr.

Bulger's mugshot, aged 81.

Bulger's mugshot, aged 81.



Soon after this, Cyr became pregnant, which was not part of the plan. “He explained to me that he was involved in loan sharking and gambling, and he was organizing things that were a little dangerous and pregnancy didn’t fit. It was too dangerous for him,” she said.

Like a snapshot from a Hollywood movie, Cyr described how one night they couple got caught in a shoot-out.

“Jimmy picked me up and put me down on the floor, and he’s on top of me trying to get a gun out when the baby kicked him. In the middle of bullets flying he looks down at me and said, ‘What the f**k was that?’”

“I said, 'oh, the baby just kicked,'” said Cyr.

Though Bulger never lived with Cyr and their son Douglas Glenn Cyr, he stayed with them once or twice every week and spent time with his family, but fear was never far from his mind.

Unfortunately, Bulger’s son’s days were numbered and at the age of six, he suffered from Reye's syndrome, caused by some medicine a doctor gave him for vomiting. Douglas was hospitalized on a Friday night and by Monday he was brain dead.

“I said to him, ‘Honey we’re going to have to pull the plug.’

“Jimmy said, ‘I can’t do that.’ He said, ‘Lindsey, I can shoot people, but I can’t do that,’” Cyr said.

Douglas passed away that night and it was a terrible blow to Bulger.

“Jimmy was colder. I remember when we were walking out of the hospital the night that he died, and he was holding my hand. Jimmy said, ‘I’m never going to hurt like this again.’”

Cyr said in 2010 that it had been 15 years since she last saw Bulger. He fled from South Boston after being indicted for murder. She believes him to be somewhere in Europe.  

She was proven wrong, however, in 2011 when he was arrested in Florida along with his longtime girlfriend Catherine Greig. Having been accused of serving as an informant for the FBI providing information on rival gangs in Boston - a claim Bulger always refuses - he fled in 1994 when tipped off about an upcoming racketeering indictment by a former FBI handler. 

When arrested five years ago, then aged 81, Bulger stood charged with 32 counts of racketeering, money laundering, extortion, and weapons charges, including complicity in 19 murders. He was found guilty on 31 counts on August 12, 2013, and is still a prisoner at the United States Penitentiary Coleman II in Sumterville, Florida

*Originally published in 2010. 

James "Whitey" Bulger's - Lindsey Cy, claims that she had a 12-year affair with Bulger and they had a son together named Douglas Glenn Cyr,. Public Domain / WikiCommons