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Jan. 24, 2010

Whitey Bulger was his dad

The never-told story of the gangster and his little son

Douglas Cyr, the late son of James “Whitey” Bulger and Lindsey Cyr of Weymouth, at about two years old.Handout/-

Since he slipped the grasp of law enforcement and vanished 15 years ago this month, James “Whitey’’ Bulger has been exposed as many things - a remorseless killer, a manipulative FBI informant, the sordid inspiration for movies that fill theaters and enough books to bust a shelf.

Now another portrait can be added to his list: devoted dad.

Speaking publicly for the first time, Lindsey Cyr, 64, of Weymouth, told the Globe that she and the former South Boston crime boss had a son, Douglas Glenn Cyr, who was born in 1967 and was healthy and active until he suddenly fell sick and died in 1973 of Reye’s Syndrome, a severe reaction to aspirin.


Cyr, a court reporter, said the boy had Bulger’s blue eyes and blond hair. She described the gangster as a nervous but warm and attentive father, who lavished gifts and time on the little boy, to the extent his demanding criminal schedule allowed. She said he worried constantly that his enemies would target the child if they knew Douglas was his, and was devastated when the boy died.

“He changed after Douglas died,’’ Cyr said. “He was colder.’’

The boy is believed to be Bulger’s only child and his parentage was known only to his closest criminal associates and perhaps some family members. Her account of their relationship, revealed in a series of lengthy interviews, can’t be confirmed in some particulars, but a Globe review suggests strongly that her description of Douglas as Bulger’s son is true.

One former mob associate of Bulger’s said he was aware that Bulger had a son.

“He did talk about the kid,’’ he said. “He told me he had a son once and that he died from Reye’s Syndrome . . . He seemed a little melancholy. You could tell it bothered him.’’


The former associate said Bulger kept the relationship a secret. He said Bulger used to say, “If you’re going to be a criminal you shouldn’t have kids becauseeverything you do affects them.’’

That Whitey fathered a child with Cyr was apparently known to others in the Bulger family. A friend of William M. Bulger, the gangster’s younger brother, said the former Senate president has a “dim’’ recollection of the child and his death at an early age and that the Globe was on “firm ground’’ to report it. Cyr said she and Whitey occasionally visited William Bulger’s South Boston home, with Douglas in tow.

Federal law enforcement officials became aware of the relationship and the child after Bulger fled, and have questioned Cyr about her claim that the fugitive criminal has called her twice since he left town - once in January 1995 to say goodbye and again in 2002 or 2003.

During the last call, which she said was made to her home after midnight, Cyr said she asked Bulger “Do you want to come home?’’

Lindsey Cyr was Whitey Bulger's girlfriend and mother of his son. John Tlumacki/Globe Staff

“There was dead silence on the other end of the phone,’’ Cyr recalled, then said Bulger replied, “I’m never going back to jail.’’ She said she did not know where he was calling from, or where he is now.

Cyr said she has been interviewed by investigators from the multi-agency Bulger Task Force repeatedly since late 2003. And investigators say they are taking her claims about the telephone calls seriously, even though she didn’t tell them about the second one until last year. She revealed the first call during her initial interview with the task force six years ago.


Gail Marcinkiewicz, a spokeswoman for the FBI, said the Bulger task force investigated Cyr’s claim about the calls from Bulger “to determine whether we can extrapolate any information which would allow us to determine where Mr. Bulger has been or might be today.’’

She declined to say whether the task force has been able to corroborate Cyr’s claims, citing the ongoing investigation and hunt for Bulger, who is wanted for 19 murders, including the strangulation of two women.

Cyr said she had decided to speak out as a prelude to writing a book about her relationship with Bulger. “I’m sick and tired of him being portrayed as a mad man,’’ said Cyr. “That’s not the man I know.’’

She said she met Bulger in 1966 when she was 21 and juggling two jobs in Quincy, working as a waitress at a diner and as an assistant to a local lawyer. Bulger, who was 15 years older, was operating a jackhammer with a construction crew working near the diner when he noticed her, she said.

Unaware at the time that Bulger had just served nine years in federal prison for a string of bank robberies, Cyr said, “He was very nice, very gentlemanly, gorgeous manners, handsome.’’

She said the relationship became serious, then she discovered she was pregnant. “He was panic-stricken,’’ Cyr said. She said Bulger wanted her to have an abortion, but she refused.


Cyr said she had a difficult labor and after giving birth to Douglas on May 22, 1967, at Jordan Hospital in Plymouth, she woke to find Bulger sitting by her bed. She described him as an anxious father, who held his newborn “like he was holding a time bomb’’ and was afraid he’d break.

Bulger attended Douglas’s baptism, at the Pilgrim Congregational Church, but he insisted, Cyr said, that he not be not listed as the father on the child’s birth certificate. Instead, Cyr listed a former boyfriend, Richard Cyr, as the father and also changed her own surname from Chester to Cyr.

Richard Cyr, who was married and having an affair with Lindsey before she met Bulger, told the Globe that he is convinced he was not Douglas’s father.

“Douglas had blond hair and blue eyes and doesn’t look anything like me,’’ he said in an interview. “If you saw my two sons, you’d say, ‘Those are Richard’s kids.’ You’d have never said that looking at Douglas.’’

Douglas Cyr, late son of James “Whitey” Bulger and Lindsey Cyr, circa 1971.Handout/-

Cyr said Bulger never lived with her, but visited her and Douglas at least one or two nights a week, and took the boy on boating trips and to family cookouts. Bulger, she said, also covered some of the cost of Douglas’s child care.

But some aspects of Cyr’s narrative about the relationship cannot be verified or do not check out. For example, she said Bulger tried to hide his ownership of bars, real estate properties, and motor vehicles by putting their legal titles in her name, but none of the public records for the properties reflect that. And other incidents that should have been easily verified, like the night she said she and Bulger escaped a hail of bullets when leaving Triple O’s bar in South Boston, were rejected by others who were Bulger confidants at the time.


Pressed on the discrepancies, Cyr stuck to her account of the incident at Triple Os, but said that perhaps Bulger lied to her when he said he was using her as a straw owner of his property.

She had no explanation as to why she didn’t tell the task force about the second call from Bulger until last year. But she did say she didn’t want to do anything that would hurt Bulger.

Friends and relatives confirmed her recollections about Bulger’s relationship with Douglas. Mary Travers of Weymouth, who lived at the time in Cyr’s neighborhood, recalls Bulger as a visitor to Cyr’s house and said he often drove two of her daughters home after they had baby-sat for Douglas. Travers said she was introduced to Bulger for the first time after the child’s funeral.

Cyr “introduced him as James Bulger,’’ Travers said. “She asked me afterwards what I thought of him. I said he was perfectly nice. I thought he was a lawyer and she laughed her head off when I said that.’’

When the 6-year old was suddenly stricken with a high fever and extreme nausea and rushed to Massachusetts General Hospital in early October 1973, Bulger maintained a vigil by the boy’s bedside with Cyr while doctors struggled vainly to save him, Cyr recalled and others confirmed.

“When he died, Jimmy was out of his mind,’’ Cyr said. “Tears were streaming down Jimmy’s face.’’

Bulger paid for the boy’s funeral and accompanied Cyr to the church service and burial, but their relationship changed after Douglas’s death as he was adamant about not having any more children, she said.

They broke up around 1980, she said. After that, she said, he surprised her on a couple of occasions in the late 1980s and early 1990s by showing up unexpectedly when she needed help or calling.

Cyr vividly recalled one surprise phone call from Bulger, the one right after he fled town for good. She said she was awakened when the phone rang at 3 a.m. It was Bulger and he told her he was going away.

“There’s going to be some trouble, but don’t worry you’re not involved,’’ Cyr quoted Bulger as telling her. And, he told her, she should not worry about him as he had “insurance and it was gold-plated.’’

He did not explain what he meant, but Cyr speculated he was referring to his secret alliance with the FBI.

Cyr said she doesn’t recall if the next call came in 2002 or 2003, but that was it was after midnight, in February, around the time of her birthday.

Bulger, Cyr said, told her he knew she had contacted Thomas R. Kiley, the attorney for his brother, William Bulger. The fugitive criminal warned her not to get involved in a congressional inquiry that was underway at the time into the brothers’ relationship.

“I said, ‘Billy is having a hard time,’ ’’ said Cyr.

Whitey Bulger agreed, she said, then told her, “I can’t help him and you don’t have to . . . Be a good girl.’’

If Cyr did receive that call from Bulger, she would be one of the last people known by law enforcement to have had contact with him.

Kiley said he had no recollection of receiving a call from Cyr, but said it might have happened.

During the last phone call, Cyr said Bulger reminisced about their time together. She said she asked him, “Are you all right?’’ and he said, “Of course. I’m having a good time. Everything is all right.’’

Marcella Bombardieri of the Globe Staff contributed to this report. Shelley Murphy can be reached at ; Stephen Kurkjian at