What You Didn't Know About the "Boss of Bosses"

Amazon.com Widgets
Carlo Gambino was only once arrested and charged, though the case
never resulted in anything. Gambino had been truly untouchable.

To set the stage for an upcoming story, we planned to post here the New York Times report on Albert Anastasia's assassination in 1957.

While researching a planned preface to the Times story, however, we learned some interesting things about Carlo Gambino.

As these tidbits accumulated, we realized our preface had grown into a story all its own.

As part of Vito Genovese's plot to remove a key enemy and solidify his power in the mob, Albert Anastasia was hit in 1957 in the barbershop of the Park Sheraton hotel in midtown Manhattan. He'd taken Carlo Gambino into his confidence to thwart his rivals on the Mafia Commission.

We interviewed a well-regarded Mafia author about Anastasia's last day -- and that is what this upcoming story concerns.

Genovese, not long after his formal "coming out" at the doomed affair that was Appalachin, found himself living out his days in prison, though he was still powerful and his word was enough to send men on the street to their deaths. (Anthony "Tony Bender" Strollo was among them.) Another order that Genovese passed on too late (depending on who you ask) concerned a soldier known as "Joe Cago." Genovese's kiss of death (Il bacio della morte) served ultimately to piss off Joe Valachi. Whether it actually happened, however, is another question, though the kiss is mentioned in Peter Maas's The Valachi Papers as well as The Valachi Papers film, which starred Charles Bronson but was still a middling effort. We admit here we didn't screen Valachi's spoken testimony out of expediency but even if Valachi said it, there's still reason for doubt.

Appalachin was important in Gambino's case, also, in that it heralded his rise to power within America's Cosa Nostra. The Feds didn't realize this until five years later, however. According to a memo from May 1962, the quiet, not tall Sicilian with the nose of a hawk suddenly transformed into a priority for J. Edgar Hoover's G-men.

It is imperative that every effort be made to establish highly confidential coverage of Gambino in view of his position as a "Commission" member and his obvious importance as a top leader in the criminal organization controlled by the "Commission." Considerable information has been developed recently indicating that Gambino is of key importance at the top level in the organized crime underworld in this country as an arbitrator and consultant.... 

Because of Gambino's key position on the "Commission" it is of utmost importance that we obtain the desired coverage of his activities, enabling us to stay currently informed on his contacts with some of the most important racket figures in this country.

Gambino served for two decades as the absolute ruler of his family (and had a strong influence on other families, including the Genovese family). Low key and secretive, Gambino set the standard followed by countless other mobsters of his day (and probably these days.) Still, while he lived relatively modestly he was indeed of legendary wealth, stashing cash, jewels and other valuables in safety deposit boxes in banks spread across New York City. He also was renowned for his ability to put together up to $10 million in cash at a moment's notice.

The FBI referred to him as "Boss of Bosses" of "LCN" and "the most powerful racketeer in the country."

When he was arrested in 1970, he refused to sign a form that noted he'd been advised of his rights. His only remark to the agents was that he had only a few months left to live, so he had nothing to say.

We'd thought he'd never been caught on wiretap even though the Feds had supposedly bugged his Brooklyn home.

Turns out, Gambino was caught on a wiretap.

A young Gambino, Mangano crime family member.

Based on Gambino's FBI files, agents installed a bug in a hotel room he shared with his wife (and alleged first cousin) Catherine née Castellano (yes, sister to Gambino's chosen successor). It was during a March 1962 vacation in Miami at the Golden Gate that the Feds heard conversations between the two.

While very personal and not very incriminating, the dialogue humanizes the man versus the myth. Gambino, based on his words, enjoyed gambling on horses -- and was not above threatening his wife with violence, though he was likely using hyperbole.

As the Friends of Ours blogger (to whom we owe a special thanks) noted, Gambino gloated about his "days at the track" while....

... Catherine complained about the Jews. Apparently Mrs. Gambino had an anti-Semitic streak: "She also stated that there were too many Jews there and she says she feels these Jews drink too much. She stated that she feels she is better than they are."...

The marriage sounded thoroughly loveless with endless bickering based on the FBI eavesdropping of the Gambino hotel room. Carlo on one occasion called Catherine a "shrew" with "a sharp tongue," and on another occasion cursed at her and "then told his wife that she talked too much and if she did not shut up, he would cut her tongue off."

"Shrew,"  a woman of violent temper and speech, is an interesting term for Gambino to have used. He seems to have had a quite extensive command of English, not his first language.

Gambino's marriage to a first cousin prompted remarks from both the FBI and Gambino's criminal cohorts, one of whom, a front boss for the Genovese family, was murdered
As the Friends of Ours Blogger noted, "the historic incident of some blood marriages in Carlo Gambino's lineage prompted Attorney General Robert F. Kennedy during a November 4, 1963 visit to the New York field office to "express[] an interest" on the subject.

The FBI compiled a family tree on Carlo Gambino in an FBI November 13, 1963 report, and the Bureau notes "that hoodlums in referring to the Gambino family ('Cosa Nostra' family) sometimes call them 'degenerates' and it is believed that this terminology may have come about through this close intermarriage within various members of the family." (The FBI files on Thomas "Tommy Ryan" Eboli indicate that the Genovese acting boss never could stand Gambino, and an informant told the FBI in the early 1960s that Eboli characterized the Gambino crime family as "full of degenerates" after learning one of its soldiers was whacked for having an affair with his mother-in-law.)

Gambino is considered to be behind Eboli's murder. As noted in a previous story, Gambino found a better cohort in Frank "Funzi" Tieri than Tommy Eboli, who placed himself in the doghouse by failing to accept the burden of repaying a $4 million loan he owed Gambino and the other bosses, all of whom had pooled their money to fund a large drug deal Eboli had put together. However, when the deal went south, Eboli wouldn't repay them or even acknowledge the debt.
Gambino supposedly had him whacked in 1972. The shooters purposely waited until Eboli was leaving his mistress's house before opening fire on him. Tommy Ryan was a boss, so why not let him go with a smile on his face? Now we wonder if Gambino had gotten wind of Ryan's characterization of the family that to this day carries the Gambino name. Perhaps there was greater impetus to the Eboli hit than previously known...
Gambino also arranged for Funzi Tieri to take over the Genovese family, supposedly to establish a base of supporters for his designated heir, Paul Castellano. Tieri proved himself to be an effective Cosa Nostra boss in how own right, however, known to be capable of applying violence only when necessary. Also, he was a big moneymaker. One FBI agent called Tieri a "real money maker, one of the classiest gangsters in the New York City area."
Gambino arrested in 1970; nothing came of it.  (Bettmann/Corbis)


(Yes, we know that Philip "Benny Squint" Lombardo (October 6, 1908 – April 1987) is considered to have been the real boss of the Genovese crime family from the late 1960s until the early 1980s. However, he seemed to have stayed under the radar while Gambino had one of his front bosses killed and appointed the next. (There is grounds for debate here, and we're sure we'll get some below.)

Gambino's career in the Mafia extended back to the 1930s (he arrived in the U.S., specifically in Norfolk, Virginia, in December of 1931, having traveled as a stowaway aboard the S.S. Vincenzo Florio).

The first mention of him by law enforcement was in the form of a memo by the U.S. Treasury Department's Alcohol Tax Unit in November of 1934. It read:

Since the coming of Prohibition, there has been in the City of New York and vicinity and extending into the State of New Jersey a notorious, daring group of bootleggers known as the GAMBINO outfit. The principal members of this outfit are: CARLO GAMBINO; his brother PAUL GAMBINO; and their cousin ANTHONY GAMBINO.

Despite all the years the FBI investigated Gambino, the Feds only were able to make one serious effort to nail him -- and it failed. The aging Don was put in handcuffs on March 23, 1970 for allegedly masterminding a conspiracy to hijack a $6 million armored car. When arrested he was in possession of around $350 in cash and hundreds more in savings bonds.

Almost every FBI memo pertaining to Gambino from then on labeled him "Armed and Dangerous."

Gambino and three others, names redacted, faced a one-count indictment. A trial date was set for December. The judge initially limited the pending trial to the afternoon hours, between 2pm and 5pm, allowing for periodic breaks owing to Gambino's heart condition, so it likely was not a major shock when Manhattan federal judge Marvin Frankel severed Gambino from the trial due to his ill health. Gambino supposedly was to face trial as soon as his health improved, a scenario never realized.

Details of the case were redacted but the FBI was careful to share information with its field offices in Boston and Newark, based on their respective "interests" in the proceedings.

The feds even investigated charges that Gambino was behind a string of bank and armored car robberies though he was only ever charged with the one-count indictment.

Among Gambino's few indulgences was the purchase of a waterfront property in Massapequa, Long Island for weekend and summer use. Gambino bought the place from Ettore Zappi, one of his trusted capos who ran a porn empire for the crime family and lived next door. The mob boss was said to have owned a 1964 20-foot Glasspas and a 1958 55-foot Wheeler cabin cruiser. Also, according to the Feds it was "reported that GAMBINO uses a converted Coast Guard cutter" though this was not confirmed.

Gambino died at this Long Island estate at the age of 74 (in a "state of grace," according to a priest who provided him with the Last Rites of the Catholic Church) on October 15, 1976.
Four days later a memo from the New York Field Office to the FBI Director provided the final details on Gambino's death:

CARLO GAMBINO died of heart disease 10/15/76 at 34 Club Drive, Massapequa, LI, NY (not verified by death certificate). GAMBINO waked at Cusimano and Russo Funeral Home, 10/16-17/76. Funeral services held 10 AM 10/18/76 at Our Lady of Grace Church, Ave. W and E. 4th St., Brooklyn, NY. Burial services followed at the Cloisters, St. John's Cemetery, Queens, NY.

While the extent of his power is open to debate, it can be said of Gambino with certainty that, in him, American law enforcement faced a true Mafia powerhouse and mastermind, a man who'd been literally untouchable.