5 of the Deadliest Mafia Hitmen in History

Joseph "The Animal" Barboza testifying in court in 1972. New York Daily News

The most feared men in the underworld are typically not the bosses, or the brash, flashy gangsters who grab headlines. They are the silent killers. The nameless, faceless men who murder for hire and disappear without a trace. Below are the stories of 5 deadly mob hitmen who left behind a trail of bodies while maintaining a relatively low profile.

“Pittsburgh Phil” Strauss

Harry “Pittsburgh Phil” Strauss was a feared enforcer for Murder, Inc., the gang of killers employed by various organized crime groups in the 1930s and 1940s, primarily in New York. Strauss was born in Brooklyn, New York in 1909 and quickly fell into a life of crime. By the age of 25, Strauss had already been arrested 17 times in New York City. As was typical of organized crime figures of the day, Strauss was never convicted for any of these early transgressions. An Assistant District Attorney in New York said Strauss “had never been convicted of so much as smoking on a subway platform.”

“Pittsburgh Phil” Strass on the right. Pinterest

By the time Strauss was a full-blown assassin for Murder, Inc., he used many tools to get rid of witness, enemies, and anyone else who had crossed the mafia. He carried a knife, gun, and an icepick so he could choose between weapons when killing a target. Strauss was sometimes sent out of town to conduct business, including the high-profile murder of Harry Millman of the Purple Gang in a diner in Detroit.

Strauss continued to murder throughout the 1930s, until a fellow Murder, Inc. associate decided to talk to authorities and pin a number of crimes on his fellow gang members. Abe “Kid Twist” Reles cooperated with police, and Strauss was just one of the names he named. Strauss was arrested for the murder of gangster Irving “Puggy” Feinstein in 1940. Reles’ account of the murder could be counted on by police: he had participated in Feinstein’s killing.

During his trial, “Pittsburgh Phil” Strauss attempted to convince the judge and jury that he was insane. He grew a long beard, stopped showering, and made a point of chewing on a leather briefcase strap throughout the ordeal. The jury wasn’t buying the act, however, and Strauss, along with his companion Martin “Bugsy” Goldstein, was sentenced to death in Sing Sing Prison’s electric chair, known as “Old Sparky.” On June 12, 1941, Strauss and Goldstein were executed. As for the informant, Abe “Kid Twist” Reles; he mysteriously fell from a window and died while under police protection in November 1941.

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  • Theseus

    Richard “The Iceman” Kuklinsky stated, during an interview while in prison, that he had killed more than 100 people and that it was probably, “Upward of 200”.
    He was a very large man, about 6′ 8″ tall and weighed about 300 lbs. He admitted to having killed someone that he considered, “my friend”, merely because the man made a statement that Kuklinsky considered to be a threat against his family.
    The forensics psychatrist,, Dr. Park Dietz, studied the footage of the interviews of Kuklinsky and told Kuklinsky that he lacked the emotion of fear. Because of this lack, Kuklinsky was able to murder people without remorse.

    Although his records are sealed, I think that the story of Dominick Montiglio, former hitman for the Gambino family, should have been included in this group. He is a former Army Green Beret with tours in Vietnam and was known to have been involved in numerous deaths for the family.

    • NiccoloM

      Because he claimed to have killed a lot of people it is taken on face value even though many of his claims have been disproved.

      • Theseus

        Because who’s claims have been disproved, NicoloM?
        And what is your statement in reference to; “Because he claimed to have killed a lot of people”. Are you saying that JUST because someone makes a claim that doesn’t mean that what they say is true and that Richard Kuklinsky is known to have lied quite often, therefote, he should not be on this list?

        • NiccoloM

          He shouldn’t be on the list because he doesn’t have more than 5 confirmed kills, at least one of which he fucked up, and many of the kills he claims are either unsubstantiated, dubious, or have been disproved (including Demeo, Hoffa, and Castellano). He was a pathological liar. Meanwhile the list is missing Roy Demeo, probably the worst of them all, the Gemini Twins, Scarpa. and a large number of other hitmen with far bigger numbers.

    • Sammy The Bull Gravano

      Eff Montiglio. He’s got a gambling and alcohol addiction and refuses to take responsibility for it.

      • Theseus

        Yeah, he’s got problems, me too, but Montiglio is like the others on this list and that comments have been about; someone who did some hard core stuff. He should be on this list before Kuklinsky should.
        No disrespect, Sammy The Bull Gravano, not wanting to be on your bad side, just my opinion.

      • PaC SGM (R)

        So are you the real Sammy the bull Gravano or just a fan of his?

      • Bob Tobey

        I hear you have turned queer Sammy. And your daughter is a fat piece of trash

        • Sammy The Bull Gravano

          That’s really supposed to bother me? Please!!!!! Go be keyboard gangster somewhere else.

    • NiccoloM

      Dominick Montiglio wasn’t a hitman. He was involved in 1 hit in which the bullet was not traced to him. He probably was more involved than he admits but no evidence suggests he was crucial to the Demeo crew. His main job was running errands for Gaggi.

      • Theseus

        Thank you for the information. I need to use more than one reference source.
        Can you shed any light on the (truth?) of his military service?
        I have read that, because of him having been a federal government witness and in the WPP, all of his military service records are “sealed” but are there any places where that information was available prior to the records being sealed?.?….

        • NiccoloM

          I only know what he claims. He was supposedly a Green Beret. He appears to have PTSD which would explain the drug habit, but he doesn’t talk anymore. Read Murder Machine and then Sins of My Father. He covers a lot. He doesn’t claim to be a hitman though.

          • Theseus

            Thanks for the information. I’ll look for the book….

      • michael foster

        And the story of him being Special Forces also seems false. He was on active duty less than 3 years, 1 of those in SEA….the training schedule for S/F’s would not allow enough time to complete boot, airborne, all the S/F’s then a tour in Vietnam and duty as a military cop at Bragg and be seperated in something like 30 months….

        • NiccoloM

          He was in the army for something but I am kinda dubious he was special forces too.

        • Broy72

          During Nam you went straight from boot to jump school then straight to special forces training. Entirely possible. Not as rigorous or advanced as today’s training.

  • Carter Stevens

    Frank ‘The Irishman’ Sheeran should have been on this list. but nobody really knows him.That will change if “THE IRISHMAN” film ever gets made.

    • Steve Sestrich

      “I heard you paint houses.”

    • Jay Smart

      Yeah- I heard of him- on his deathbed he admitted to killing Hoffa

    • Anthony Tod

      It’s being made. Deniro plays the Irishman and Pacino is Hoffa. Martin Scorsese is directing.

    • valleevue

      No other cultures “Hero Worship” these people like us Americans. I’ve been to Italian restaurant/pizza places with Goodfella ,Godfather posters,Capone,Gotti and other MUGSHOTS posted and on another wall references to NYPD with hats and Old Glory ….equalizing the two groups? . My “Gangster is tougher than your Gangster” mentality. Grown men wearing Capone ,Gotti , Billy the Kid , Jesse James Tee shirts. Don’t make them warriors being tough and brave .Killers as the headline here says but not warriors.

  • Ron Barth, Jr.

    What, no Chicago? Frankie “The German” Schweihs and Harry “The Hook” Aleman could/should be in here. No one fucked with Chicago while Accardo ran it and these guys were available.

  • Brad Brinker

    WHERE IS ” THE GRIM REAPER”??????????????????

  • MrProgressive

    Where’s Dexter Morgan?

  • Jay Smart

    What about Jimmy “the carburetor” Buntz or Louie “the wheel bearing” Schleppy then there’s Vinny “tail light cover” Palmetto last but not least Tommy “turn signal” Solero they were all great hitmen from the outfit Midas Inc . Headed by the infamous brothers Gary “Gearshift” and Doug “the oil pan” Mancino

  • GumbaJ

    Morbidly fascinating.

  • Will

    Surprised no Whitey Bulger.

  • craigaaaw

    Kuklinski said that he killed a stranger with a cross-bow just to see if it would work. Another time, Kuklinski tied up a guy in a cave, set up a video camera, and taped the guy being eaten by rats. Kuklinski said he regretted the way he killed just one guy. He had the guy locked in a room, when the guy began to pray out loud, he told the guy he would be back in 30 minutes to see if God changed the circumstances. After a half hour, Kuklinski came back and murdered the guy.

  • Vincent Mileto

    Out of these 5 killers, only one was an Italian, and he lived in Italy.