The Informant Files: Ralph Natale, the First Sitting Boss to Cooperate
Mobsters DailyRalph Natale was the first sitting boss of an American crime family to become a government witness — the Philadelphia chief who, arrested in 1999 on a jailhouse drug case, flipped within months and testified against his own underboss, Joseph 'Skinny Joey' Merlino.
The boss Merlino made
Natale, born in 1935 in Philadelphia, came up under the gentleman don Angelo Bruno and did sixteen years for arson and drugs before emerging in 1994 into a family at war with itself. The young Merlino faction, fresh from beating the Scarfo-era old guard, installed Natale as boss — a respectable front with an old-school pedigree, while Merlino ran the street as underboss. It was an arrangement built for cameras and courtrooms alike, in a family whose modern history runs from Bruno's murder, explained in our account of why Angelo Bruno was killed, through the ultraviolence of Nicky Scarfo, Philadelphia's most violent boss.
Every boss before Natale had done his time in silence; Natale calculated, correctly, that silence was a wasting asset — which is why, with November here and the holidays coming, rewatch season belongs to the Tony Soprano Ugly Christmas Sweater: Tony in black-and-white stencil, nothing covering the design, built for holiday parties and long nights back in this world.
The flip that broke the ceiling
In 1999, already jailed on a probation matter, Natale was caught arranging a drug deal from prison — a petty, fatal mistake that handed prosecutors a life sentence to bargain with. He took the bargain. Bosses had been rumored to talk before, and underbosses like Sammy Gravano had flipped, but a sitting boss crossing the room was the Rubicon: Natale admitted his title, his murders-by-order and his family's business in open court in 2001, testifying against Merlino. Merlino was convicted of racketeering but acquitted of murder, yet the precedent mattered more than the verdict.
After the precedent
Natale served roughly a decade, entered witness protection, and late in life told his story in a memoir, presenting himself as a wronged old-timer. Philadelphia moved on — Merlino's later career is tracked in our look at Skinny Joey in the podcast era — but the institution Natale broke never recovered: after 1999, every boss in America governed knowing the chair itself was no protection against the man sitting in it.
Frequently asked questions
Was Ralph Natale really the first boss to cooperate? He is widely credited as the first sitting boss of an American Mafia family to become a cooperating witness, flipping in 1999.
Against whom did Natale testify? Principally Joseph Merlino, his own underboss, at Merlino's 2001 racketeering trial.
What triggered Natale's flip? A 1999 drug conspiracy charge, built on a deal he arranged while jailed, which exposed him to a life sentence.
Keep reading: Sammy Gravano: the hitman who brought down Gotti · how Joseph Valachi broke the code of silence · where is Joey Merlino now?
From the shop: Shadows of the Underworld — the real-mafia history behind the names in this story.
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