Who Is Stephen Flemmi? Age, Biography, and Wiki
Stephen Flemmi, born on June 9, 1934, is an infamous American convicted murderer and former mobster who became notorious for his involvement with organized crime in Boston. By 2025, he is 90 years old. Flemmi was deeply entrenched in the mob’s operations and is known for his connections with figures like Whitey Bulger. His life story involves not only the criminal underworld but also his eventual cooperation with law enforcement, leading to significant developments in the prosecution of organized crime in America.
| Occupation | Criminals |
|---|---|
| Date of Birth | June 9, 1934 |
| Age | 91 Years |
| Birth Place | Boston, Massachusetts, U.S. |
| Horoscope | Gemini |
| Country | U.S |
Popularity
Stephen Flemmi's Popularity over time
Height, Weight & Measurements
At the age of 90, Stephen Flemmi's physical attributes are not publicly documented as they might be for younger celebrities. However, during his prime, he was noted to have a typical build for a man involved in physical crime, presumably around 5 feet 9 inches tall with a weight that varied throughout the years depending on his lifestyle choices.
Family, Dating & Relationship Status
Stephen Flemmi's family background has been marred by tragedy and crime. He has a complex relationship history filled with illicit partnerships. Although there is no documented current girlfriend or spouse in 2025, his past relationships were often intertwined with his criminal lifestyle. He is known to have had romantic entanglements that reflect the tumultuous nature of his life. Given his age and legal restrictions, it is unlikely that he is pursuing any new relationships.
He was raised in the Orchard Park tenement located at 25 Ambrose Street in the Roxbury neighborhood of Boston, Massachusetts. His father was a bricklayer and veteran of the Royal Italian Army during World War I, and his mother was a full-time homemaker.
Net Worth and Salary
As of 2025, Stephen Flemmi's net worth is a subject of speculation. During his criminal career, he amassed considerable wealth through illegal activities, but the forfeiture of assets due to his conviction has significantly impacted his financial standing. Estimates suggest that his net worth could be in the range of several hundred thousand to low millions, largely dependent on the legal battles he faced and any remaining assets he could reclaim post-incarceration.
Career, Business, and Investments
Flemmi's criminal career was highlighted by his role in organized crime with the Winter Hill Gang. His activities included various nefarious methods of income generation, ranging from extortion to drug trafficking. After cooperating with federal authorities, his career as a mobster ended, and he became a key witness in the cases against other mob figures. In recent years, there have been no known legitimate business ventures or investments on his part, given his past and current restrictions.
After leaving the military, Flemmi, along with his brother Vincent, joined the Roxbury Gang in the late 1950s. The gang was led by the brothers Walter, William and Edward "Wimpy" Bennett and controlled bookmaking and drug dealing in the Roxbury and South End neighborhoods of Boston.
A soft-spoken and slender man of around 5-feet-8 and 140 pounds, Flemmi operated out of the Marconi Club, a combination bookmaker's, massage parlor and brothel, in Roxbury. Although he had a reputation as a ruthless killer, Flemmi was a popular man who was fond of nightlife, cars and the company of young women.
Social Network
Due to his notorious past and felony conviction, Stephen Flemmi maintains a very low profile in social networks. It is highly unlikely that he engages with mainstream social media platforms due to legal limitations and the personal risk associated with his notorious reputation. There are, however, various fan pages and discussions about him within community forums that explore the history of organized crime.
When the third Bennett brother, William "Billy" Bennett, "began vocalizing his belief that Flemmi had murdered both his brothers", Flemmi "reluctantly decided" that he too must be killed.
56-year-old Billy Bennett was dumped from a moving car and found dead against a snowbank in the Mattapan neighborhood of Boston on December 22, 1967 after getting into a vehicle with Richard Grasso, an associate from South Boston. Stuart assisted Flemmi in post-killing cleaning after Bennett's murder.
A week later, Grasso was shot twice in the head and left in the trunk of his 1967 Buick Wildcat in Brookline. Grasso was killed by Flemmi after he had "panicked" because his car was used in Billy Bennett's murder. After the killings of the Bennett brothers, Flemmi assumed control of the Roxbury Gang.
Education
Details regarding Stephen Flemmi's formal education are sparse, reflecting many individuals involved in organized crime during his era. He likely received a basic education but dropped out at a young age to pursue a life of crime. This lack of formal education has contributed to his criminal mentality rather than a scholarly approach to life.
In conclusion, as we look at Stephen Flemmi in 2025, we witness a life marked by crime, controversy, and a long journey through the American justice system. His past actions have left a profound impact on the world of organized crime and law enforcement.
