Gaspar DiGregorio – The Banana Boss

Gaspar DiGregorio was a New York Mafia boss who led the Bonanno crime family during the so-called “Bannana Wars” of the 1960s. He played a key role in one of the bloodiest periods in mob history and helped transition his family from its original management to a new generation of leaders.

DiGregorio was born in Sicily in 1905 and immigrated to the United States through Canada in 1921. He settled in the Williamsburg neighborhood of Brooklyn. He got his start in crime as a bootlegger, and it was in that trade that he first met his future boss and enemy, Joseph Bonanno, as well as other key mobsters on the way up.


The mob wars of the late 1920s opened a door to organized crime for DiGregorio. In the final years of Prohibition, the New York Mafia was largely divided between two men: Joe Masseria and Salvatore Maranzano. Each had allies, and each wanted the same thing: total control of the mob.

Most of the up-and-coming gangsters sided with Maranzano. They included Bonanno, Charles “Lucky” Luciano, Benjamin “Bugsy” Siegel and Meyer Lansky. The Castellammarese War was long and bloody, but the Maranzano organization was better equipped. DiGregorio fought for the winning side.

The hostilities finally ended in 1931, when Masseria was murdered in a Coney Island restaurant. That put Maranzano in charge, and he proceeded to divvy the mob into its present structure.


Maranzano cut America’s organized crime network into 24 pieces, with each “family” electing its own boss. Beneath the boss would be the underboss, then the caporegime, or lieutenant, and beneath him the soldier. New York would have five families: Maranzano (now Bonanno), Luciano (now Genovese), Mangano (now Gambino), Gagliano (now Lucchese) and Profaci (now Colombo).

At the top of it all would be the capo di tutti capi, or boss of bosses. Maranzano appointed himself to this position.

But he didn’t hold it for long. He may have been victorious in the Castellammarese War, but another battle was brewing, and he was on the losing side. Maranzano was a Mustache Pete, an old-school Sicilian who believed in ethnic barriers and liked to raid the till.

The men who worked for him, particularly Luciano, were Young Turks who believed in business above all, even if that meant working with Jews and other ethnic groups. Maranzano knew the Young Turks were trouble, so he arranged a hit, but Luciano got wind of it, and Maranzano was rubbed out in 1931.

That made Joe “Don Peppino” Bonanno the boss of Maranzano’s family, the youngest don in New York, and gave DiGregorio a leg up too. Bonanno gave him his own crew and appointed him capo.


DiGregorio led a relatively quiet but productive criminal life for the next 30 years. He hoped to become consigliere someday. He married the sister of Buffalo don Stefano Magaddino and was best man at Bonanno’s wedding. He was godfather to Bonanno’s oldest son, Salvatore “Bill” Bonanno.

But eventually Bonanno began to resent his fellow Mafia bosses and believed he was entitled to outrank them. So he cooked up a coup d’état of epic proportions: He hired hit man Joseph Colombo to rub out three New York bosses and one in Buffalo so he could climb to the top.

Colombo, however, knew he would die if he carried out the job, so he ratted Bonanno out to the other bosses. Bonanno quickly went underground, and in October 1964, he faked his own kidnapping. In his absence, he appointed his son, Bill, boss.

The other bosses refused to acknowledge that arrangement, however, and put DiGregorio in charge of the family. Open mob war erupted on the streets of New York as a result.


One half of the Bonanno family favored the old boss and fought tooth and nail to restore him. The others agreed that Joe Bonanno had reached for too much power, and fought just as hard to stop him.

DiGregorio was trying to put down the opposition and keep Bill Bonanno out at the same time. Bodies began to pile up, and the bosses feared the feds might jump in and cause more trouble for everyone. They called a truce meeting at a house in Brooklyn.

DiGregorio prepared for Bill Bonanno’s arrival with sniper’s nests. Bill, whose father had taught him to be paranoid, parked a block away, spotted a gunman, and managed to escape after an intense firefight.

Joe Bonanno finally reappeared in 1966 and tried to stop the killing. But his demand that his son be allowed to lead the family was too much for the other bosses, still outraged at his assassination attempt. They insisted DiGregorio stay in power, and the war continued.


After more months of bloodletting and no settlement in sight, the bosses began to tire of DiGregorio. The war wasn’t ending and he wasn’t getting the job done. They wanted the Bonanno faction dead or subdued.

So they pulled the plug and got behind mobster Paul Sciacca as the new boss of the Bonanno family. With no support, DiGregorio was effectively shut out of the Mafia after leading one of its most important families through a period of turmoil and bloodshed.

The Banana Wars finally ended in 1968, when Joe Bonanno reappeared and suffered a heart attack, then retired to Arizona. His permanent departure from the scene squelched the last of the Bonanno faction in the family and united leadership behind Sciacca.

DiGregorio spent the last years of his life with his family on Long Island. He died June 11, 1970, of lung cancer in Smithtown, N.Y. He is buried at St. Charles Cemetery in Farmingdale, N.Y.

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