Whitey Bulger - Personal Life

Personal Life

Bulger fathered one child, Douglas Glenn Cyr (1967–1973), during a 12-year common law marriage with Lindsey Cyr, a waitress and former fashion model. Bulger and Cyr began living together in 1966, when Cyr was 21 and a waitress at a North Quincy cafe. According to Cyr,

"He used to say that there were four people he had turn up on a street corner for: Douglas, me, Billy, or his mother. And we all made him vulnerable."

At six years of age, Douglas died from Reye's syndrome after having a severe allergic reaction to an aspirin injection.

According to Cyr,

An absolute nightmare, and it was very difficult for Jimmy because, no matter what, there was nothing that could save this. Money didn't matter, his power didn't matter . . . I remember that we were walking out of the hospital the night that he died, and he was holding my hand. And Jimmy said, 'I'm never going to hurt like this again.'"

Since Bulger's arrest, Cyr has publicly announced her support of him, stating

If he wanted to see me, I'd be happy to. If he needs help getting attorneys and what have you, I'd be happy to help him. Part of me does (still love him). I still care for him. I would always help him. I certainly always stand by him. He is the father of my child. He is 12 years of my life. I want to see him well protected . . . And I'm not particularly sympathetic to some of the people involved, some of the victims' families.

After his split from Cyr, Bulger began a relationship with Theresa Stanley, a South Boston divorcée with several children. Bulger bought her an expensive house in suburban Quincy, Massachusetts, and acted as father to her children while commuting to "work" in South Boston. However, he was repeatedly unfaithful to her with a host of other women, and was often absent while overseeing the running of his organization. In a 2004 interview, Stanley stated that she is planning to publish her memoirs.