Whitey Bulger fathered one child, Douglas Glenn Cyr (1967–1973), during a twelve year relationship with Lindsey Cyr, a waitress and former fashion model living in North Weymouth, Massachusetts. Bulger and Cyr began living together in 1966, when Cyr was 21-years-old and a waitress at a North Quincy café. According to Cyr, "He used to say that there were four people he would 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 syndrome after having a severe allergic reaction to an aspirin injection. Lindsey Cyr later recalled it as:
"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.'"
After Bulger's arrest, Cyr 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."