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The Shoot-Out on Troutman Street: The Mafia at War

By Thom L. Jones for Gangsters Inc.

In January 1966, a civil war broke out. Not between different people in a country, but within a family. A family of criminals that operated across the five boroughs of New York. It had been brewing for a while, and now it was time.

Between instinct and action, there is no edit function. This would cause a lot of pain and suffering before the final body fell. Unlike Sicily, where they really know how to carry out mob wars, this one would be an itty-bitty affair. However, it would occupy a lot of people over the years it rumbled along.

Gaspare Di Gregorio was “A Boy of the First Day.”(1)

He was one of Joe Bonanno’s closest friends, and best man at his wedding in November 1931. A cousin of Stefano Magaddino, who was also a relative of Joe, another cousin.

Photo: New York Mafia boss Joseph Bonanno

Magaddino was identified as the boss of the Mafia of Buffalo, western New York, and southern Ontario before the McClellan Senate Investigating Committee in 1963.

These familial relationships would turn out to be troublesome and conflicting.

Gaspare would marry Maria Magaddino, another cousin, sister of Stefano, although their time would be short, and hopefully, sweet. She was dead in 1927 at the age of twenty-three.

Thousands of words have been written about the “Banana War” as the internecine battle involving Bonanno’s Crime Family became known. However, Gregorio’s part has been mainly underplayed, and yet he was a significant catalyst in the drama that played out over the months before and after the Troutman Street affair.

Whatever started the war, the trigger was ambition fertilized by nepotism. Reasonable traits when you are a king, tricky when you deal with the edge of darkness filled with psychopaths and stone-killers.

Born in Trapani Province, Western Sicily, in 1905, Di Gregorio emigrated, legally or illegally, to Canada and from there to New York in 1921. He settled in Brooklyn in the Roebling Street area of Williamsburg, which was a center for many of the Bonanno clan and their associates when they first arrived in New York in the early 20th Century.

He would link up with his brothers, Bartelemo, Antonino and Matteo, who had already settled in the district. They operated an illegal distillery and ran bootleg liquor across the city during Prohibition.

By 1931 he was a close friend of Joseph Bonanno, who had been elected to head his own Mafia Family following another “war” that had broken out between quarrelsome factions in New York’s underworld. This ended in September 1931, just in time for Joe’s wedding. (2)

The two men had become such close friends, that Di Gregorio was Joe’s best man and became the godfather of the Bonanno’s first son, Salvatore, generally called Bill.

On taking over the Mafia Family, after the murder of its former boss, Salvatore Maranzano, in September 1931, Joe appointed Gaspare as one of his captains and set him up with his own crew of men. What could go wrong? Everything, as time would disclose.

Di Gregorio (right) was mister average. Medium in build, about five-seven and one-fifty-pounds, bespectacled, gray-haired, mild-mannered in appearance, he was never convicted throughout his criminal career. Although arrested in 1934 as a suspect in the killing of two Brooklyn hoods, Pietro Turrigiano and Pietro Caleca, the charges were dismissed. Law enforcement sources referred to him as a “sleeper.” He lived on Long Island and owned and operated a garment manufacturing plant, F&D Coat Company in Brooklyn, and another similar business on Long Island. His homes, from 1946 onward, in Rockville, then West Babylon, Long Island, were boringly mundane. Married a second time, to Vita LaSala, they had three children. He was beige almost to the point of invisibility.

Joe Bonanno referred to him “as most deficient in leadership qualities,” yet made him a captain of his Mafia soldiers.

Joe also claimed he was too slow of thought and ineffectual.

Bill Bonanno maintained Gaspare was not a person who had the stomach for violent conflict, although he had been the point man on raids during the “war” of 1930-31 and also the driver and bodyguard of Salvatore Maranzano,  a job not generally given to a pussycat.

Then there were the two murders in Brooklyn. DiGiorgio was perhaps a much bigger “sleeper” than anyone realized.

The conflict involving the Bonanno Crime Family, sometimes also referred to as “The Banana Split,” had its roots in Canada, which were watered and nurtured in Brooklyn.

In 1963, Joe Bonanno applied for Canadian citizenship. He had interests, legitimate and criminal, north of the American border. Stefano Magaddino (right) came to believe his cousin was making a move on his Buffalo and Canadian operations.

He told a friend, “Joe’s planting flags all over the world.”

According to information that emerged after the event, Joe had also set his sights on becoming the Boss of New York's Mafia. To achieve this, he decided to kill Carlo Gambino and Tommy Lucchese, two powerful mob bosses in the city, along with his cousin, Magaddino and the boss of Los Angeles Mafia Family, Frank De Simone. This one was a bit off-side, although Joe had interests in California, not unlike in Canada, legit and left of center. 

Such an absurd scenario, it’s hard to believe it was taken seriously by both the media and law enforcement.

Even more unbelievable, to organize and carry out this mammoth rub-out, Joe hired a man from another Mafia Family in New York, Joe Colombo, who was a captain in the family under Joe Profaci.

With over 300 soldiers in his own army, it’s hard to understand why Joe needed a mercenary.

Instead of carrying out the contract, Colombo chickened, ran to Gambino, and confessed all. To muddy the waters, even more, it was also suggested that Joe Magliocco, underboss of Profaci’s Family, and running it since his boss had died of cancer in June 1962 was linked into the conspiracy. Magliocco was another uncle of Bill’s wife and a close associate of Joe Bonanno.

Gambino and Lucchese, (close personal friends and related by the marriage of their children,) along with Magaddino, chairman of the board, demanded The Commission, the mob’s arbitration panel, summon Joe to a hearing, which he ignored, to explain his conduct.

Bonanno had also promoted his son Bill (left) in February 1964, into the position of consigliere, or counselor, the number three position in his Crime Family, overlooking many more senior men within the group. Especially Gaspare Di Gregorio, who Magaddino, believed more worthy of the promotion following the retirement of John Tartamella after he suffered a stroke that left him restricted to a wheelchair.

In theory, the Family underboss, John Morales, should have resolved this problem, but he had become almost redundant because of the familial ties between father Joe and son Bill. Morales was also maintaining a low profile due to pressures from the law and those being developed within the crime Family and would be replaced by Frank Labruzzo. Morales disappeared from the headlines, and it seems, the Bonanno Family, and died of natural causes in 1984.

If ever there was a double to toil, a cauldron to bubble and a fenny snake to fillet, this was it. (3)

And so, it began.

These events were taking place before the rainy, wind-swept evening of October 20, 1964, which was when Joe Bonanno was kidnapped by two men while walking on Park Avenue, Manhattan.

Newspaper columnist Walter Winchell reported that Bonanno was being held by Magaddino at a farm in upstate New York. Magaddino was subpoenaed in May 1965 to appear before a special grand jury probing the Bonanno disappearance. He did not testify, as he developed coronary symptoms the next day and was hospitalized. The press reported that it was the second time in five years that Magaddino’s health problems handily coincided with a demand for his testimony.

Joe Bonanno reappeared as if by magic some nineteen months later, walked into a federal courthouse in New York and wondered if someone was looking for him. It’s alleged that in January 1965, The Commission formerly appointed Gaspare into the position of boss of the Bonnano Family. At this point, maybe up to one hundred soldiers had defected and moved over to the other side.

From then until February 1969, when perhaps the final victim in the war, Thomas Zummo (right) was shot dead in a Queens apartment building, it would be a time of chaos for Joe, his son, Di Gregorio, and the mob world of New York.

As confusing and disorganized as the night on Troutman Street.

There are three versions of what happened that evening in January-from the horse’s mouth, so to speak. One is actually from its withers as it is hearsay through the narration of Bill Bonnano’s biographer.

Joe states in his biography that his son, along with Frank Labruzzo and Joe Notaro, were ambushed on their way to a meeting with Di Gregorio. Note: On their way.

Gay Talese, the biographer of Bill, has a similar take with the group getting hit as they were walking to their destination.

Thirty years after the event, Bill Bonanno’s account is more dramatic, with a more complicated scenario. He states, with some drama, “We were caught in the middle of a battlefield, with nowhere to go.”

He also introduces us to another of his gang, Carl Simari, who enters the picture for the first time.

Frank Labruzzo had been contacted by Sorreno Tartamella, John’s son, acting as an emissary for the Di Gregorio faction that wished to heal “The Banana Split.”As a sign of their honest intention, it was suggested Bill name the rendezvous point and the time.

Reassured by this approach, Bill agreed and suggested the home of his grand-uncle, Vito Bonventre, who lived at 283 Troutman Street (photo below), in Bushwick. A long-established Bonanno Crime Family enclave, he would feel safe in this neighborhood.

A white-weather-board row house, it is located on the west side of the street, between Knickerbocker Avenue to the south, and Irving Avenue to the north. Built-in 1931, the property to-day is shown as a two-story building housing four apartments. It may well have existed that way in 1966, because of an incident that occurred there this night, Friday, January 28.

Bill and two companions drove from his home at 1555 Tyler Avenue, in East Meadow, Long Island, in his white, 1964 Lincoln auto, and parked a few blocks from the venue. He, Labruzzo and Simari, (no mention of Notaro,) walked to the house and there, met up with “others” who had already assembled.

Around midnight, Bonventre receives a telephone call to say Gapare has been taken ill and can they postpone the meeting until the following week. As Bill and Simari, followed by Labruzzo and Joe Notaro, leave the property, they come under gunfire from somewhere across the street. The shooters are either in a house, behind parked cars, or the closed and shuttered fruit and vegetable stalls that line the sidewalk.

Under a heavy barrage, estimates run from twenty to two hundred shots were fired that night, Bill and Simari, scuttle down the street, firing back with their own handguns. They reached Knickerbocker Avenue, and then made their way to safety. 

No one knows how many gunmen were there that night, although the police subsequently found seven discarded weapons, and another was found a day later, in a nearby street, and believed to be part of the collection. We can, therefore, assume, allowing for no two-gun wielding hit men that there was at least eight. Reasonable to double that number in the belief that many of the gunmen were smart enough to keep their guns as they ran. And ran they did. Like a murder of crows, the hit-squad flew everywhere but killed no one.

In their panic and sheer stupidity, they fled, like ants from a toppled nest, in all directions,  dropping weapons as they ran. One of the shooters was so frightened and disorganized, he raced away, through a  front door, into a house, terrifying a young woman he passed in the hallway. Dropping his weapon, he vanished into the night through the back yard into Starr Street to the south-east.

Or did he?

Police arrived soon after the shooting ended, called in from the nearby Wilson Avenue station house.

They interviewed over one hundred people who knew nothing. Maybe someone was letting off fireworks. Happened all the time. The television was on. They were asleep. In an area suffocated by the Mafia’s ominous and parochial presence for over fifty years, it was to be expected.

Then there was Josephine Cipponeri. She had plenty to tell. She was the only one of the witnesses the police interviewed who admitted that the shoot-out had occurred. She was in her ground-floor apartment, in bed, when a man smashed his way through her front door, rushed passed her down the hallway, and disappeared via the backyard into the night.

Her address was 283 Troutman Street.

So here we have the possibility that one of the crazed shooters disappeared from the scene by actually running through the very house he had been sent to target. The myth of efficient Mafia killers evaporates like so many stories about their invincibility. Good at shooting someone in the back, but head-on, facing an enemy that could return fire, even when outnumbered as Bill and Simari were, the gang collapsed like the proverbial pack of cards.

Months later, when summoned to a Kings County Grand Jury, Bill recognized one of the many guns on display collected in and near Troutman Street. He knew it belonged to Philip “Rusty” Rastelli, one of  Di Gregorio’s top gunmen. If this was the best, it’s easy to understand how bad a job they did. Rastelli was so bad, he eventually became the family boss, also indicating, just how low it was sinking.

A mountain of speculation built on a foundation of assumption, the Grand Jury saw everything and nothing. Troutman Street was The Bermuda Triangle of a Mafia war that could have been taking place in Uganda as far as New York was concerned.

According to District Attorney, Aaaron E. Koota, on July 7 1966 in the supreme court of Kings County:

“On or about January 28, 1966 there was a considerable volume of gun-fire in the vicinity of 283 Troutman Street, Brooklyn, Kings County, New York. At the scene of the occurrence, members of the New York City Police Department gathered up some seven fire-arms and many expended shells. In the course of an investigation into the shootings the Police Department and the District Attorney's office became convinced from evidence obtained by them that the incident was an overt act by one group of gangsters who were waging a contest with another group for the leadership of an organization engaged in Kings County in such criminal activities as gambling, illicit dealings in narcotics, usury and other crimes.”

Sometime that year, as Bill Bonanno sat talking with Labruzzo, he ruminated on the strange world they were occupying. In a world moving into high-technology and space exploration, the Bonanno’s were fighting each other like peasants in Sicily during the 19th Century.

“We’re in the wagon-wheel business,” he said, and Labruzzo had agreed. (4)

Five minutes drive north of Bonventre’s house, in Ridgewood, Joe Bonanna’s group would carry out their most publicized attack against the other faction, in November 1967. A gunman dressed in black, walked into a restaurant and machine-gunned three men to death. Mass Mafia murder, in public, on this scale would not be repeated until the 1972 killing of two meat company executives, shot dead in a Manhattan Italian restaurant. A tragic case of mistaken identity.

The Bonanno group killed three more in September 1968. Still, as these men simply vanished one day in September, they were never officially recorded as fatalities in the war. According to New York

Public Prosecutor, Walter Phillips, said the Bonanno War involved twelve public shootings, six men were killed, and six wounded. The last to go was Tommy Zummo, and his end-note simple confirms how complicated and mixed up the “Banana War” really was. (5)

In November 1968, Joe Bonanno finally abdicated and moved to Tuscon, Arizona, where he died, aged ninety-seven in 2002. His son Bill, after spending eleven years in prison for various criminal acts, also moved south and died in Tuscon in 2008. He was seventy-five.

Gaspare Di Gregorio’s luster as head of the split-faction seemed on the wane before Troutman Street. After it, he was in effect, history. Following multiple heart attacks, he stepped down and was replaced by Paul Sciacca, who, himself was replaced by Natale Evola, another ‘Boy of the First Day.”

Although he suffered multiple heart problems in his later life, in the end, it was cancer that felled Gaspare. At sixty-five, he died in June 1970, a patient in St John’s Hospital, Smithtown, Long Island.

There are three definitive books on the Bonanno’s. (6)

The first, published in 1971, tells the story through the eyes of an outsider who became a confidant and close friend of Bill Bonanno.

The second is Joe’s biography, released in 1983.

Lastly, Bill’s recollections which came out in 1999, completes the trifecta. (6)

Interestingly, each book title contains the word honor as though it were some holy grail marker in the strange Mafia world of so-called respect and tradition.

Although there had been mob killings and shoot-outs on the streets of New York over the previous sixty-years, there was never something on the scale of Troutman Street. The biggest bang, but paradoxically, the loudest whimper in a Mafia civil war.

Footnotes:

(1) Joe Bonanno referred to his wedding groomsmen in this way. At least six of the seven were, or became, part of, the Mafia Family that Bonanna would come to lead in the weeks before his marriage, following the end of what the media referred to as “The Castellammarese War,” a crime syndicate control dispute between four Mafia clans across New York.

(2) One of the groomsmen was Salvatore Profaci, brother of Guiseppe, who founded his own family around 1927 or 1928 in South Brooklyn after his arrival in America from Villabate, Palermo. Salvatore’s daughter, would one day marry Bonanno’s son. During the “war,” the Profaci Family sat on the side-lines, like a mongoose watching the other four Mafia Families strike at each other like spitting-cobras. Maybe this boss waited and watched for the spoils of war that would drift his way when the dust settled.

In the distant future, his own family would rip itself apart, not once, but twice.

(3) Double, double toil and trouble;

     Fire burn and caldron bubble.

     Fillet of a fenny snake,

     In the caldron boil and bake.

Macbeth. William Shakespeare.

(4) High Notes: Selected Writing of Gay Talese. 2017. Bloomsbury. New York.

Referring to the way early settler’s covered wagons circled against attacks of Indians during the expansion of the West during the 19th Century.

(5) All sources claim Zummo was an associate connected into the Di Gregorio faction. Yet he was murdered by one of their own men. Zummo was gunned down in the lobby of his girlfriend’s apartment in Queens on February 6, 1969. The man who shot him was Joey Massino. They were both, twenty-nine years old, both associates in the Crime Family that was now under the control of Paul Sciacca.

Zummo worked under Frank Mari, who was almost certainly the man in charge of the shooters at Troutman Street, and Massino was mentored by Rusty Rastelli. Massino would become the Family boss one day, and the only New York Mafia head to ever become a co-operating law enforcement witness.

In a state-of-siege mentality that seemed a hall-mark of Bonanno gunmen, having fired multiple times at his target, missing more times than he hit, as he ran away, the semi-automatics magazine slipped out and was left behind. Massino sweated for days that his fingerprints would be traced from this, but somehow, he survived, to kill another day.

(6) The three books are in order of publication:

Gay Talese, Honor Thy Father, New York: Random House, 1971.

Joseph Bonanno, A Man of Honor, London: Andre Deutsch Limited, 1983.

Bill Bonanno, Bound by Honor, New York: St Martin’s Press, 1999.

The image of Di Gregorio is posted on website mafiahistory.us run by well-known crime historian, Tom Hunt, and I acknowledge this accordingly.

For more of Thom L. Jones' stories, check out his Mob Corner at Gangsters Inc.

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