Famous Mobsters Who Served In The Military

Stephen Flemmi was not just an associate, but the right-hand man of infamous South Boston Irish mobster Whitey Bulger and his White Hill Gang. Among his mobmates, he was known as "the Rifleman," according to a 2018 exposé from The New York Times. The two were so close that the Times called Flemmi: "in essence, the Italian-American twin of Mr. Bulger, an Irish-American." In fact, when the FBI was looking for informants, it recruited them as a pair.

Flemmi was not called "the Rifleman" for nothing. He had earned that nickname during a period of his life when it seemed he might avoid a life of crime. At age 17, Flemmi escaped the rough streets of Boston by enlisting in the army in 1951, per Boston journalist Beverly Ford's book "The Boston Mob Guide." Flemmi was sent into the thick of the action, where he earned his nickname and skills that would serve him well in organized crime.

Flemmi was assigned to the 187th Infantry and shipped out to Korea, where he thrived, spending some time as a paratrooper. He was considered a deadly sniper, racking up a Bronze and Silver Star — both awards for acts of valor. During a 2021 plea for compassionate release from prison, it was revealed that Flemmi was entitled to a monthly payment of $1,334, per The Boston Globe, due to "service-related disability," suggesting he was also wounded during his service. He received an honorable discharge in 1955, but went into a life of crime upon returning home to Boston.

Salvatore "Sammy the Bull" Gravano was "Teflon Don" John Gotti's underboss, hitman, and downfall. Speaking on the Jordan Harbinger Show, Gravano explained that although he came from a Brooklyn family of "good hard-working people," he struggled with dyslexia in school, was expelled, and went into a life of street crime.

In 1964, Gravano was drafted into the U.S. Army and assigned to the infantry and communications. He was trained to run orders communications to the front line. But most importantly, he was "taught to kill." He was honorably discharged in 1966 before he could be sent to Vietnam, although he later told Peter Maas he would have been fine with it, since at least the government would have decorated him for killing people.

After the service, Gravano became a Cosa Nostra hitman. He later turned FBI informant against Gotti, partly because of Gotti's comments about Desert Storm in 1991. According to The New York Times, Gravano and Gotti were in custody and would watch news of the war. Gravano complained that "[John was] rooting for Iraq to win the war for our troops to die and this and that ... we hate the Government. But what do these kids got to do with it? I mean, like it or not, we belong to this country." This insult towards American servicemembers influenced his enmity towards Gotti, and in the end, Gravano provided the crucial evidence that finally put the "Teflon Don" behind bars.

Edward Eastman did not go into the military as a young man, intending to turn his life around. He already had nearly two decades of organized crime experience while running the streets in New York City in the early 20th century, per the Mob Museum. His gang, known as the "Eastman Gang," was involved in larceny, sex work, and some narcotics dealing. By the time he joined the service in 1917, he had at least three stints in prison before volunteering for the battlefields of Europe in World War I.

Eastman signed on as a volunteer with the 106th Regiment of the 27th Infantry Division. No one knew who he was — and he thrived. He was seen as a "tough older brother" to the younger enlistees and draftees, and had no qualms about throwing himself into the trenches in the face of enemy fire — he already had plenty of experience doing that in the streets.

Eastman saw hard action during the war, particularly during the Second Battle of the Somme in 1918. He was shot, gassed, and even charged with insubordination for leaving a field hospital to return to the fighting, despite having a leg wound. In the end, after finding out who he was, his comrades lobbied New York Governor Al Smith to pardon Eastman, after his battlefield heroics became front-page national news. However, this did not reform Eastman. As soon as he got out of the service, he went into bootlegging and got himself killed. He was given a full military funeral — ironically, with a police escort.

In 2007, New England veterans' groups were split when the death of former Boston North End Patriarca family underboss, Gennaro Angiulo (above left), was announced. According to the Boston Herald, Angiulo was entitled to a full military funeral, complete with six Navy pallbearers, a flag-draped coffin, a bugle, and a gun salute from active service members.

As it turned out, Angiulo had earned a funeral with at least some honors. Before making a career in organized crime, which ended when violent White Hill Gang bosses and FBI informants James Bulger and Stephen Flemmi got him locked up, Angiulo had distinguished himself in the Pacific theater during the Second World War. His job was steering landing craft — a dangerous job that involved piloting boats filled with soldiers onto mined beaches, while under enemy fire. He achieved the rank of chief bosun's mate, which gave him the right to private accommodation and better food.

Angiulo's funeral raised some mixed feelings among area veterans. One said he should have "got the firing squad years ago" — military service notwithstanding — thanks to his racketeering activities and two decades in prison. However, another interviewed said that while a full funeral was probably too much given his criminal past, he had served his country valiantly before entering organized crime, while a third simply said that if he had risen so high in the military, he at minimum deserved his flag. In the end, it seems the funeral went along as planned.

George Barone is best known for his criminal career and as the founder of the Jets street gang — eventually immortalized in Jerome Robbins and Leonard Bernstein's "West Side Story" — per the Village Voice. He later moved on to Cosa Nostra, serving as a Genovese hitman, where he racked up as many as 20 murders (that he could remember) before turning federal informant.

What is less known about Barone is that before his life of crime, he was one of "The Few, The Proud." That's right — during World War II, Barone served in the U.S. Marine Corps during its bloodiest battles against the Japanese in the Pacific Theater. According to military records, and Barone's own words to the New York Post, he participated in a grand total of five major battles, including the invasions of Guam and Saipan, and the bloody Battle of Leyte Gulf during the American invasion of the Philippines.

For Barone, however, it was his service in Iwo Jima that would have made him a hero, had it not been for his later criminal history. Although there are few specifics, Iwo Jima was the Marine Corps' bloodiest day, with over 24,000 casualties. Barone lived it all and likely experienced all the hardships, although it doesn't seem that he ever discussed his experiences in detail. He did come back with a medal for good conduct and plenty of ribbons, though. Despite attempts to make a legitimate living with the Merchant Marines, he eventually fell into organized crime.

Umberto Anastasio, better known as Albert Anastasia, was the capo of Murder Inc. He already had a handful of convictions under his belt by 1939, including a stint on death row for a 1921 murder of a longshoreman and a firearms arrest in 1923, according to a 1957 exposé by The New York Times. Nevertheless, he escaped the electric chair and went on to become one of Cosa Nostra's most feared figures, earning himself the nickname, "the High Lord Executioner," according to Mafia historian Thomas Hunt's site Mafia History.

By 1942, the pressure was on Anastasia, who was under investigation for a series of murders dating back to 1933. So he chose to disappear into the ranks of the U.S. Army. He signed on as a technical sergeant with the U.S. Army at Indiana Gap, Pennsylvania, where he used skills obtained in the underworld to train longshoremen to unload ships quickly and efficiently.

During World War II, foreigners who served in the U.S. military could be fast-tracked to citizenship (Anastasia had first entered the U.S. illegally in 1919). He took full advantage of the program, but omitted his entire criminal past from the application — even though newspapers had reported on his criminal history with headlines such as "Murder, Inc. Ace Now Army Top Sergeant." He got his citizenship and a discharge for being overage in 1944. Unable to ditch life in the mafia, he returned to crime and was assassinated at a barbershop in 1957.

Dominick Montiglio was a Gambino hitman and extortionist, reportedly bringing in up to $250,000 per week in extortion money for his superiors, and according to him, the FBI believed he and his crew had been involved in nearly 200 murders. So where did Montiglio become so good at killing? He honed his skills as a Green Beret on the front lines of Vietnam.

Montiglio described his military service in a later interview, during which he noted the terrifying confusion of being in battle when all he could see were muzzle flashes, as well as his first kill — and the following self-reported 93 he accumulated as a sniper. He also joked about being the "****ing new guy," when no one would talk to him until he proved himself in a firefight. He said that while it was scary, it made him a warrior, and he did not understand why anyone would not want to experience the same.

Montiglio's comrades also remembered him fondly. In a separate interview, Vietnam veteran Benjamin Whipple spoke highly of Montiglio. Whipple said that he, Montiglio, and several other men patrolled, drank, and partied together in Saigon. On the battlefield, Montiglio, according to Whipple, took part in the bloody battle of Dak To, where he was up on the hill in the thickest part of the fighting and was wounded. Whipple did not find out about Montiglio's criminal history until Montiglio called him to tell him he was in the witness protection program.