Douglas Glenn Cyr was the one and only son of late American organized crime boss James Joseph “Whitey” Bulger and his ex-wife Lindsey Cyr. Although Douglas lived for a very short period, he gained notoriety as the son of a former gangster. Read ahead to find out more about his personal life events, death details, tragic short life, and more.

Quick Introduction

Douglas Glenn Cyr was born on 22 May 1967 in Plymouth, Massachusetts, United States. He was born to James Joseph Bulger Jr., a notorious killer and one of the FBI’s most wanted, and Lindsey Cyr, a waitress and former fashion model. He was the grandson of Jane Veronica Bulger and James Joseph Bulger Sr.


Personal Life Events

Life of James Joseph “Whitey” Bulger

James Joseph “Whitey” Bulger was born on 3 September 1929 in Everett, Massachusetts. He was born to Irish immigrants. His father, James Joseph Bulger Sr., was a union laborer and occasional longshoreman. Bulger’s childhood was spent in miserable conditions after his father lost his arm in an industrial accident. He had two younger brothers, William Michael “Billy” Bulger and John “Jackie” P. Bulger.

While his brothers did well at school, he was drawn into street life. Billy served in the military during the Korean War and also served for eight years as President of the Massachusetts Senate. For Bulger, Billy, Douglas, Lindsey and his mother were his weak points. He could do anything for them.

Criminal Charges

Living in South Boston, he garnered a reputation as a thief and street fighter. Local police gave him the nickname “Whitney” because of his blond hair. However, he disliked this name and preferred to be called “Jim,” “Jimmy,” or even “Boots”. He served in prison for the first time from 1943 to 1948 after being charged with larceny, assault, forgery, and armed robbery.

Bulger became the leader of the Winter Hill Gang in the Winter Hill neighborhood of Somerville, Massachusetts. He was included in the FBI’s Ten Most Wanted Fugitive list in 1999 after he became a fugitive in 1994. He was found guilty on 31 criminal counts, including participation in 11 murders after a two-month trial in 2013. Bulger was given two consecutive life sentences plus five years.

How Did His Parents Meet First?

In 1966, Lindsey, a resident of Weymouth, Massachusetts, met the crime boss Bulger at a cafe. She fell in love with him instantly as he was gorgeous, handsome, blond, and blue-eyed according to Lindsey. They started dating and she gave birth to their son Douglas the following year. They had a 12-year-old relationship.

Tragic Short Life

Douglas had a very tragic short life. He lived in this world only for six years. He was the biggest achievement for his father. Unfortunately, his death shook him completely.

Death Details

In 1973, Douglas Glenn Cyr died from Reye syndrome after having a severe allergic reaction to an aspirin injection, at age 6. Although his father is known for his heinous crimes, he was very sensitive in the case of his son. Unfortunately, on October 30, 2018, his father was beaten to death by inmates within 12 hours of his arrival at Hazelton.


Douglas Glenn Cyr was the son of America’s most wanted crime boss James Joseph Bulger Jr. However, Bulger was a doting father to his son.