Gaspare Di Gregorio – “The Sickly Don”

After many Commission meetings of bosses across the country, Gaspare was selected to lead the Family. But his reign was short-lived.

Gaspare (Gasparino) Di Gregorio was born in 1905 in Castellammare del Golfo (Trapani province), Sicily. He immigrated to this country illegally through Canada in 1921.

He originally lived on Roebling Street in the heart of the Williamsburg section of Brooklyn until buying a home at 162 No. Forest Avenue in Rockville Centre in 1946.

In 1962, he relocated a bit further out on Long Island to a modest home at 737 Fifth Avenue in West Babylon (valued at $20,000 in 1966).

By the late 1960s, he sold his home and moved in with a daughter and son-in-law at their Smithtown, Long Island home where he would live out his final years.

Gaspare DiGregorio

He had a wife and three children, one of whom Anthony, would later join his father in the life. He also had two brothers (Matteo and Antonio) who became mafiosi as well. The DiGregorio brothers operated in tandem for years.

His daughters and son were all very close to him. After getting married, they all lived either on the same block or within a few blocks of he and his wife.

He was approximately 5-foot 7-inches tall and 150-pounds. He wore glasses and had a quiet, low-key demeanor.

His activities included bootlegging, gambling, extortion, shylocking, garment rackets, and strong-arm enforcement.

Gaspare was an Original

He was a boyhood friend and schoolmate of Joe Bonanno and many other future top American mafiosi back in Sicily.

He was also related by marriage to Buffalo’s Steve Magaddino, Vincent Danna, James Genna, Salvatore and Dominick Sabella, Sereno Tartamella, and several other Bonanno and Buffalo members.

Di Gregorio, Bonanno, and several other young men from Castellammare started off as bootleggers during the early 1920s in Brooklyn.

Sereno Tartamella and Steve Magaddino

He was also known as an active gunman and shooter during the “Castellammarese War” years of the 1929 to 1931 era.

Gaspare had only been arrested once in his life. But it was a doozie.

It was in 1934 that Di Gregorio was arrested in connection with the strangling and shooting double-murder of two Brooklyn hoodlums, but the charges were later dismissed.

He was very close to the seat of power, namely Salvatore Maranzano, the supreme leader of all those who hailed from Castellammare del Golfo during that tumultuous time period and served as a Maranzano's bodyguard.

Joe Bonanno and Gaspare were also the closest of friends.

Salvatore Maranzano

In fact, Gaspare became “compare” to Bonanno’s son Salvatore (to be named godfather to a friend's child is considered a very high honor and sacred thing to Italians, Sicilians in particular).

Gaspare also served as best man at Bonanno’s wedding.

He was among a group of young Castellammarese mafiosi who (Bonanno included), because they had started with Maranzano from the very beginning, referred to one other as “The Boys of The First Day”!.... a reference to the base seat of future power within this borgata.

In 1934, Di Gregorio was arrested for the strangling and shooting of two Brooklyn-based hoodlums. The charges were later dismissed for a lack of evidence.

Gasparino held ownership in several garment factories over the years including F & D Coat Co., of Brooklyn and the Nina Coat Co., 350 Marconi Blvd. in Copiague, Long Island.

He was officially “inducted” early to “The Life”.

Joe Bonanno

By the mid to late-1920s, he was already a “soldier” in the Castellammarese borgata of the Mafia.

By the 1940s, he had been elevated to “capo di decina” status and was considered boss Joe Bonanno’s closest friend and sidekick.

He would hold this exalted post for several decades until being elevated to lead once the problems started within the Family.

He had long been considered a “sleeper” within the mob. Until the Family turmoil of the mid-1960s, Di Gregorio was a virtual unknown.

By 1965, informants were starting to talk about this little-known mafioso taking over leadership of the entire Bonanno Family.

Soon, law enforcement had identified Gaspare and were smothering him with surveillance and scrutiny as never before seen. And he didn’t like it one bit!

He much preferred the shadows that he’d successfully lived in his whole life.

The FBI started trailing him night and day. Surveillance cameras were capturing his every move.

He was immediately subpoenaed to testify before several mob grand juries.

He was able to largely avoid testifying by claiming a serious heart condition. The FBI, of course, weren’t buying it (but it wasn’t a lie, he’d had four previous heart attacks).

After many Commission meetings of bosses across the country, Gaspare was selected to lead the Family. But his reign was short-lived.

He hated the exposure and became a largely ineffectual boss because of the 24/7 scrutiny by law enforcement. His heart condition also did not help his tenure as head of the borgata.

He was a sick man and needed quiet and a doctor's care. That proved true shortly thereafter when he suffered another heart attack.

He was eventually replaced by a close associate and his previous aide, Paul Sciacca.

Di Gregorio numbered among his close, lifelong associates some of the most important mafiosi in both Italy and America;

• Giuseppe (Joe Bananas) Bonanno - a boyhood friend in Castellammare and lifelong associate of Gaspare, became Family Boss.

• Stefano (Steve) Magaddino - another Castellammare native, Gaspare’s brother-in-law, and Buffalo Family Boss.

• Paul Sciacca - lifelong associate, became “acting boss” after DiGregorio’s reign.

• Salvatore Maranzano - the original leader of the Castellammarese faction, former “boss of bosses”, murdered 1931.

• Salvatore Sabella - a Castellammare native, became boss of the early Philadelphia borgata.

• Carlo Gambino - Palermo native who would become boss of the Family named after him.

• Vito (Don Vitone) Genovese - started as a camorrista, later rose to Boss of the Luciano borgata, a Bonanno adversary.

• Gaspare Milazzo - a boyhood pal from Castellammare, murder suspect who fled to Detroit becoming boss. Later murdered.

• Francesco (Frankie Carroll) Garofalo - another Castellammare native who would rise to underboss, later retired back to Sicily, barber’s union president.

• Giovanni (John) Tartamella - born in Castellammare, would rise to be consigliere under Bonanno.

• Giovanni (John) Bonventre - an original power both in Castellammare and America, top capo and mentor to nephew, Joe Bonanno.

• Michael (Mikey Adams) Adamo - longtime power and capo under Bonanno, a key insurgent in later years.

.....among others, especially various Castellammarese figures throughout the underworld.

Carlo Gambino, Vito Genovese, and Frank Garofalo

There were many interrelated by either by blood or marriage, or both, in the underworld. The Bonanno Family especially.

Gaspare Di Gregorio would eventually die but not from that weak “ticker” he always complained about.

He succumbed to lung cancer in 1970.

Gaspare Di Gregorio – “The Sickly Don”

You May Also Enjoy

Anthony Crisci

Gaetano (Tony) Lisi – Drug Trafficker with a Hidden Interest in the “C.I.A.”

Vincent Cassese

Welcome Back!

Create New Account!

Retrieve your password

Are you sure want to unlock this post?

Are you sure want to cancel subscription?

Gaspare Di Gregorio – “The Sickly Don”

Unlock The Door to the Underworld

Take the Journey!

You May Also Enjoy

Anthony Crisci

Gaetano (Tony) Lisi – Drug Trafficker with a Hidden Interest in the “C.I.A.”

Vincent Cassese

Welcome Back!

Create New Account!

Retrieve your password

Are you sure want to unlock this post?

Are you sure want to cancel subscription?