Whitey Bulger

He met waitress and fashion model from North Weymouth, Massachusetts, Lindsey Cyr in 1966, after which the two shared a live-in relationship with a common law marriage for 12 years.

The couple had a son – Douglas Glenn Cyr, in 1967. However, he suffered from Reye’s Syndrome, an allergic reaction to an aspirin injection, and died in 1973 at the age of six.

After Bulger and Cyr ended their relationship, he got involved with Theresa Stanley, a divorcee with several kids from South Boston.

James Joseph Bulger Jr. was born on September 3, 1929 in Dorchester, Massachusetts, as second of the six children, to Roman Catholic Irish parents who immigrated to America.

His father, James Joseph Bulger Sr., was a union laborer and longshoreman. However, tragedy struck the family when his father lost his arm in an industrial accident and the family shifted to a public housing project in South Boston.

While his brothers were good at academics, he lived on the streets and made an attempt to run with the circus at the age of 10, thus becoming a thief and street fighter eventually.

His criminal life started at the age of 14 when he was arrested for delinquency. He became a part of the street gang ‘Shamrocks’ and was sent to a juvenile reformatory for five years, on charges of larceny, assault and battery.

Upon his release in 1948, he joined the US Air Force and served in Kansas and Idaho. However, when he revealed his true colors, he was arrested in 1950 for going absent without leave, but was discharged honorably in 1952.

He returned to Massachusetts, where his criminal offences increased, starting with his arrest in 1956 for bank robbery. He was jailed for 25 years in federal prison, but was released in 1965.

He came back to South Boston and became an enforcer for gangster Donald Killeen. After Killeen’s murder in 1972, he joined Winter Hill Gang where he transformed into a shrewd, ruthless mobster.

He carried out various murders, killing members of the rival Mullen gang, including Paulie McGonagle, Tommy King, and Spike O’Toole, apart from shooting Buddy Leonard and Edward Connors.

In 1980, he gunned down bookmaking gangster, Louis Litif, on refusing to pay his profit share, committing two murders without his permission and threatening to kill his friend, Kevin Weeks.

He shot dead cocaine dealer Edward Brian Halloran, and his friend, Michael Donahue, in 1982, when Halloran informed the FBI on having information about the Roger Wheeler murder operation and turned witness in Louis Litif murder.