Jimmy "The Shiv" DeStefano

James "Jimmy the Shiv" DeStefano (date of birth and death unknown) was an influential Italian mobster known as the "Death House Barber of Sing Sing" and associate of many notorious mobsters, most notably of the Genovese crime family.


DeStefano and his family arrived in the US around 1909 and tragedy soon struck when his father, Giuseppe DeStefano, an accomplished violin maestro died in a trolley accident. Alone in a foreign country, his mother was left with no means of support.

Fearing for her two children's well-being a matchmaking neighbor - the mother of mobster Frank Costello - found her a new husband. She married a man named Galata and died shortly thereafter, leaving her two children at the mercy of the stepfather, who despised the young Jimmy. Continual abuse forced DeStefano into the streets where he joined his friends and began a colorful criminal career that would eventually lead him to Sing Sing Prison. There, for five years, as the death house barber, he gave 46 men and one woman their final haircut.

"I never grew used to the job," he confessed in a six-part 1934 series run by the New York Journal. "Each execution was an ordeal."

Al Capone and Jimmy were working as bouncers at the Harvard Inn, where Capone got the infamous scar on his face. Their common desires to escape the stench of poverty and get their piece of the American dream bonded them for life. While working in the Harvard Inn DeStefano and Capone came into contact with an up-and-coming mobster by the name of Johnny Torrio. They admired Torrio's quick mind and looked to him as their mentor. "The Shiv" later became acquainted with Alessandro Vollero who served as a mentor to both him and Joseph Valachi.

Jimmy's many daring escapades with Frank Costello, Bugsy Siegel, Meyer Lansky and Lucky Luciano molded his future.

Lewis E. Lawes, Warden of Sing Sing Prison for 21 years met Jimmy as a young boy in the Protectory where Jimmy had already acquired the moniker "The Shiv" defending himself from the advances of a priest. Warden Lawes recognized his desperate situation and they became friends as he supported and encouraged the troubled boy. While confined in the Protectory in Brooklyn, he also became friends with Joe Valachi and Jacob Shapiro.

In 1918, mobster Frankie Yale contacted Torrio and requested that he take Al Capone and Jimmy "The Shiv" to Chicago; they were both in trouble and facing prison time. DeStefano however, was eventually caught and landed in Sing Sing for the first time in 1918.

While imprisoned in Sing Sing he also came into contact with a violent young mobster who was on death row but would later have his sentenced overturned, Albert Anastasia, who would later become a powerful and notorious mob boss. The Barber (Jimmy) told his friend Lucky Luciano that he needed someone like Albert Anastasia. Luciano managed to have a re-trial for Anastasia and killed many witnesses for Anastasia and a judge set Anastasia free.

Release from prison

After his release, DeStefano returned to a life of crime and was sent back to Sing Sing in 1927. In 1936, while out of prison, Jimmy reported to a New York City parole officer, who disliked him and the men he was connected to. Abusing his powerful position (and wanting to teach him a lesson) he beat him so severely that it nearly took his life. He, an innocent man, was shipped back to Sing Sing with bogus documents prepared by the parole officer. From there, after fourteen months with Warden Lawes's encouragement he represented himself before the New York Supreme Court, successfully winning his appeal and his freedom. He emerged from the prison shadows to marry his sweetheart, Maria Durante, the niece of famous entertainer Jimmy Durante, and lead an exemplary life.

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