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Before turning to acting, Sirico was reportedly a fast-rising mob associate of the Colombo crime family, serving under Carmine " Junior " Persico, and had been arrested 28 times.
There is a Sopranos reference to this fact when Paulie says, " I lived through the seventies by the skin of my nuts when the Colombos were goin ' at it.
" In 1967, he was sent to prison for robbing a Brooklyn after-hours club, but was released after serving thirteen months.
In 1971, he pled guilty to felony weapons possession and was sentenced to an " indeterminate " prison term of up to four years, of which Sirico ended up serving 20 months.
In an interview in Cigar Aficionado magazine, Sirico said that during his imprisonment, he was visited by an acting troupe composed of ex-cons, which inspired him to give acting a try.
According to a court transcript, at the time of his sentencing, he also had pending charges for drug possession.
Sirico appeared in a 1989 documentary about life, The Big Bang by James Toback, in which he discussed his earlier life.

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