Diksha Sundriyal
Starring Johnny Depp, the 2015 film ‘Black Mass’ focuses on the life and crimes of Jimmy “Whitey” Bulger, particularly his association with FBI agent John Connolly. Through the years, Whitey develops a reputation for himself as a ruthless gangster, becoming one of the most wanted people on the FBI’s list. But there is another side to him, apart from the murderous bloodlust that leads him to kill so many people. His softer side comes out in front of his girlfriend, Lindsey, and their son, Douglas. In the movie, Douglas’ death leads Whitey down a spiral, one that Lindsey does not accompany him on. She distanced herself from the gangster after the family’s tragedy, but that doesn’t mean she was completely out of his life.
Lindsey Cyr Saw a Side of Whitey Bulger No One Else Did
When Lindsey Cyr crossed paths with Jimmy “Whitey” Bulger, she was only 20 years old. It was in 1966 when she was working as a waitress at a diner in Quincy. Meanwhile, Bulger had already been in and out of prison. He was 35 years old and working as a construction worker in a nearby location. They fell in love pretty soon after their first meeting and stayed together for the next twelve years. Within a year of their relationship, Lindsey was pregnant and gave birth to their son, Douglas, in 1967. Lindsey revealed that Bulger wasn’t very happy when he found out about the pregnancy. For someone in his line of career, having children was a liability that he couldn’t afford. Reportedly, he told her that if she ever got pregnant again, he would shoot her.
To keep Lindsey and Douglas safe, it was decided that the boy’s existence would remain a secret because he would be an easy target if Bulger’s enemies ever found out about it. Whatever his qualms may have been about Lindsey’s pregnancy, all the doubts disappeared when Douglas was born. She revealed that Bulger loved Douglas more than anything and was devastated when the boy died six years old due to Reye syndrome. Lindsey revealed that when she talked about getting Douglas out of life support, Whitey was heartbroken and said he couldn’t do it. Eventually, when it was done and Douglas was gone, he told Lindsey that he was “never going to hurt like this again.”
The death of his only son turned Bulger into a much more ruthless criminal, but for Lindsey, this side of him never came to the surface. The only time she remembers seeing him violent is when he got into a confrontation with her ex-boyfriend, whom he “backed out of the restaurant and pulverized with four straight shots.” Apart from this, there was never a hint of a violent side in front of her or Douglas. Even after his crimes came to light and he went on the run, Lindsey said that no one could ever “convince [her] that [Whitey] is some kind of a mad killer.”
Lindsey Cyr Died a Year After Whitey Bulger’s Death
Lindsey Cyr passed away due to natural causes at the age of 74 on October 11, 2019. Apart from Douglas, she had a son named N. Alexander Cyr, though she didn’t have a long-time partner. She spent almost the entirety of her life in Weymouth, Massachusetts, which is also where she breathed her last. In her youth, she had been interested in fashion and design. She had also worked as a legal secretary for various Boston law firms and was involved in the job of court reporting as well. Her death came a year after Bulger’s, who was killed in prison in 2018. While the whole world saw him as a murderer and a monster, Lindsey continued to love him till her last days. She spent the final decade of her life talking to media and newspeople about her relationship with Bulger, trying to show a different side of him to the world.
Lindsey also openly expressed her dislike for the dark portrayal he received in the movies and documentaries about him, which she believed “made him out to be a demon.” While Lindsey and Bulger were separated in the 70s, they still remained in touch. She revealed that when he was forced to go on the run from the FBI in 1994, he called her to say goodbye and let her know he was leaving town. She said that he called her twice during his time away from the country. When he was eventually caught, she said she would be there for him if he needed her help, and she also shared her surprise over his arrest.
While there were one or two phone calls between them, Lindsey didn’t share any plans to visit him in prison. Even when Bulger was convicted for his crimes, Lindsey didn’t believe that he did everything he was accused of. According to her, he was used as a scapegoat by people who actually committed the crimes and got deals out of ratting on him. Years later, when Bulger was killed in prison, Lindsey expressed her shock on the matter, blaming the Department of Corrections for his murder. In an interview, she said that, according to her, Whitey’s death was a setup by the authorities who didn’t want him around anymore. She blamed the laxity in his protection as one of the reasons behind his death.
