The Deadliest Mafia Hitmen In History — And The Gruesome Stories Behind Them

Published October 4, 2021
Updated January 6, 2025

Gregory Scarpa, The Mafia Hitman Who Pistol-Whipped The KKK

Gregory Scarpa Mafia Hitman

New York Daily News/Getty ImagesGregory Scarpa outside his home on Staten Island.

The “Mississippi Burning” murders of 1964 left the FBI scrambling for answers. Civil rights activists James Chaney, Andrew Goodman, and Michael Schwerner were killed by the KKK after traveling to the state to participate in the Freedom Summer campaign, and their bodies were nowhere to be found.

Fortunately for the feds, they had arrested mobster Gregory Scarpa of the Colombo crime family in 1962. Facing hard time with countless bodies under his belt, Scarpa agreed to work undercover for the FBI instead. He was now tasked to solve the Mississippi case using tactics he’s picked up as a Mafia enforcer.

Gregory Scarpa was born on May 8, 1928, in New York City and was introduced to the Mafia by his older brother Salvatore in the 1950s. He was involved in everything from loan sharking and extortion to drug trafficking and murder. Eventually, he became such a prolific killer that associates dubbed him the “Grim Reaper.”

Gregory Scarpa In Court

Bettmann/Getty ImagesScarpa during his trial before the Senate Investigations Subcommittee.

Scarpa rose quickly in the Colombo ranks and soon became a captain of his own crew. He dressed snazzily and had properties in multiple states. Purportedly responsible for more than 50 murders, he never missed family dinners.

That all came to an end after his arrest and transition into undercover work. Flown down to Mississippi and given a gun, Scarpa set out to find the activists’ bodies. After kidnapping a local klansman and shoving a gun in his mouth, the answers came quickly. With the bodies recovered, Scarpa returned to New York.

Ultimately, his controversial 30-year tenure for the feds would mainly involve solving petty crimes after that. In 1992, however, the former Mafia hitman shot a man who allegedly threatened his son, and he was sentenced to life in prison as a result. In the end, he died behind bars within a year of his incarceration.

author
Marco Margaritoff
author
A former staff writer for All That’s Interesting, Marco Margaritoff holds dual Bachelor's degrees from Pace University and a Master's in journalism from New York University. He has published work at People, VICE, Complex, and serves as a staff reporter at HuffPost.
editor
Cara Johnson
editor
A writer and editor based in Charleston, South Carolina and an assistant editor at All That's Interesting, Cara Johnson holds a B.A. in English and Creative Writing from Washington & Lee University and an M.A. in English from College of Charleston and has written for various publications in her six-year career.
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Margaritoff, Marco. "The Deadliest Mafia Hitmen In History — And The Gruesome Stories Behind Them." AllThatsInteresting.com, October 4, 2021, https://allthatsinteresting.com/mafia-hitmen. Accessed February 1, 2025.