Master Manipulator: The Rise and Fall of Mobster Anthony "Tony Bender" Strollo
Anthony "Tony Bender" Strollo was incredibly conniving even by mafia standards. In April 1962, after one too many betrayals, he disappeared forever
Just Prior to the formation of The Commission and the five families, there was a bloody gang war raging in New York. The two sides were led by old-world mafiosi named Salvatore Maranzano and Giuseppe “Joe the Boss” Masseria.
Known as the Castellammarese War, The bloody conflict led to bodies in the street and a lot of attention from police and the press. Many of the participants in the conflict would later go on to prominence as some of the most infamous and well-known mobsters of the twentieth century.
Names like Salvatore “Charlie Lucky” Luciano, Vito Genovese, Gaetano “Tommy Brown” Lucchese, Joe Profaci, Albert Anastasia, Frank Costello, and many others.
Many of these men resented the arrogance and greed of their bosses and would derisively refer to them as “Mustache Petes.” The term referred to their boss’s insistence on adhering to old-world traditions and their refusal to compromise or negotiate in order to avoid further bloodshed.
Underlings on both sides quietly conspired behind the scenes to take out both bosses, as the conflict was both bad for business and left them all vulnerable.
Born in 1899 in lower Manhattan, Anthony Strollo was already an established enforcer for Joe Masseria by the time the Castellammarese War broke out in 1930.
Unbeknownst to Masseria, several of his lieutenants, under the leadership of Lucky Luciano, were conspiring to kill the boss and divide his lucrative rackets amongst themselves.
Eliminating the Bosses
According to most accounts, Luciano, on the pretext of having a meeting, lured Masseria to a Coney Island Restaurant on April 15, 1931. As Luciano excused himself to use the restroom, four gunmen entered the restaurant and executed Masseria in a hail of bullets.
Prior to Masseria’s murder, Luciano had secretly made an arrangement with Masseria’s hated rival, Salvatore Maranzano. It was agreed upon that if Luciano arranged for the death of Masseria, he would be allowed to take over Masseria’s rackets and would be given the number two position under Maranzano.
It was also decided that the mafia clans in New York were to be divided into five “families,” with Luciano being given leadership of his own family.
However, not long after this, Maranzano called a meeting of the bosses where he unequivocally declared himself to be “Boss of Bosses.” Maranzano also made sure that many of the most lucrative rackets in the city stayed within his family.
Having already begun to sour on Maranzano’s leadership, things came to a head for Luciano in September 1931 when he learned from fellow mobster Tommy Lucchese that Maranzano was planning to have him murdered.
Acting first, Luciano dispatched four Jewish gunmen to Maranzano’s Manhattan office. The men posed as government tax agents, and because they were not Italian, Maranzano did not suspect a setup.
Once inside Maranzano’s office, the men viciously stabbed him numerous times before shooting him to death.
Strollo’s Ascent
After eliminating the two most powerful mafia bosses in New York City, Lucky Luciano was now the number one mobster in the city. However, he was shrewd enough to realize that being the “boss of bosses” would only create envy and put a target on his back.
Understanding this, he set about creating “The Commission,” which was a governing body made up of the heads of the five New York City families as well as the bosses of the Buffalo and Chicago families. This panel would mediate disputes and conflicts between individuals and families.
They would also vote on matters pertaining to electing new bosses, as well as represent the interests of smaller families from other cities and states.
Rather than elevating his own position, Luciano chose to remain an equal among the four other family bosses. He became the boss of what was then the Luciano family. He chose his ally Vito Genovese as his underboss and placed Frank Costello as the family’s consigliere or advisor.
He also promoted an ambitious young soldier named Anthony Strollo to the position of captain. Strollo was placed in charge of the powerful Greenwich Village crew in Manhattan.
Strollo and his crew made significant income from gambling, as well as labor racketeering. Strollo also owned several bars and nightclubs, which further supplemented his income.
As a young man, Strollo had worked as a truck driver with the teamsters and had likely established underworld connections through this affiliation.
Having now become an influential captain in the most powerful crime family in New York, Strollo’s stock was on the rise. Soon, a series of events would propel the ambitious gangster even higher.
Becoming Underboss
In June 1936, Luciano was convicted on a pandering charge and received a hefty sentence of 30 to 50 years in prison. Underboss Vito Genovese then became the boss of the family, and he chose Anthony Strollo as his underboss.
The two had a good relationship, with Genovese serving as best man at Strollo’s wedding.
However, in 1937, Genovese was forced to step down as boss when he fled to Italy to avoid a murder indictment. Genovese wanted Strollo to maintain control of the family in his absence.
Instead, Genovese’s rival Frank Costello was placed in charge of the family, and rather than keep Strollo as underboss, he installed mobster Willie Moretti in the position.
Return of Genovese
In 1946, Genovese was extradited back to the United States to face his indictment. When the witnesses against him conveniently turned up murdered, the charges against Genovese were dismissed.
Genovese was now back to working for the crime family that would eventually bear his name. However, after a decade away from New York, the mob had moved on without him, and he was given the rank of captain.
Genovese was now the captain of the Greenwich Village crew, with Strollo as his number two. However, for both of these cunning mobsters, the demotion would only be temporary.
By now, Strollo and his wife and children had moved across the river to Fort Lee, New Jersey, where Strollo remained a powerful figure in the labor unions in both New York and New Jersey.
Strollo maintained his power through his relationships with corrupt politicians and police. He is said to have been the force behind notorious mobster and future International Brotherhood of Teamsters president Anthony “Tony Pro” Provenzano.
This move further solidified the Genovese family’s control in the Garden State.
Plot to Kill Costello
Behind the scenes, Genovese and Strollo were plotting to retake their positions at the top of the crime family.
On May 2, 1957, Strollo met with Costello for an afternoon lunch. During the meeting, Strollo learned of Costello’s plans and whereabouts for the rest of the day. Immediately following the meeting, Strollo relayed the information to Genovese, who dispatched one of his soldiers to murder Costello.
The shooter, Vincent “The Chin” Gigante, who would become a mafia powerhouse in his own right, crept behind Costello as he entered his building.
Luckily for Costello, he turned his head at the exact moment Gigante fired the gun and was only grazed along the side of his head.
Wise to the ways of Cosa Nostra, Costello read the play, and rather than go to war with Genovese and his allies, Costello chose to step down as boss of the family.
During Gigante’s trial, Costello testified that he did not recognize the man who shot him, and Gigante was set free. Vito Genovese was now once again boss of the family, with Anthony Strollo becoming the family’s underboss.
Power Play
The treacherous nature of mafia politics and alliances was further displayed in October 1957, when Genovese assisted his longtime ally, Carlo Gambino, become boss by helping Gambino plot the murder of Anastasia family boss, Albert Anastasia.
On October 25th, 1957, Anastasia was getting a shave at the barber shop in the Park Sheraton Hotel in Manhattan when two gunmen with scarves covering their faces burst into the shop and unloaded their guns into him.
This hit was beneficial for both Gambino, who was now the boss of a family, and for Genovese because one of his strongest allies was now a boss with a seat on The Commission.
Betraying Genovese
Of course, when it comes to the mafia, loyalty is fleeting, and for Genovese, the two men he had helped reach the heights of their chosen profession were now conspiring to take him out of the way.
In 1959, both Strollo and Gambino agreed to set up Genovese on a narcotics trafficking rap. That same year, Genovese was convicted and sentenced to 15 years in prison.
As fate would have it, Genovese was sent to federal prison in Atlanta, where Frank Costello happened to be serving a sentence on income tax convictions. Eventually, the two rivals began to communicate with each other and compare notes.
After their discussions, both Genovese and Costello realized that Anthony Strollo had played a key role in both of their misfortunes.
Disappearance and Theories
On April 8, 1962, after receiving a phone call from an associate, Anthony Strollo told his wife that he had to leave and would return shortly. Strollo then left the couple’s Fort Lee home. He was never seen again.
The consensus is that Strollo’s disappearance and presumed murder was ordered by Genovese.
Over the years, several people have claimed responsibility for Strollo’s death. These include a longtime Bonanno family hitman named Harold “Kayo” Konigsberg. In 1964, he offered to bring the feds to a farm in New Jersey that he called a “mafia cemetery” where Strollo and at least a dozen other bodies were buried.
However, the feds did not take Konigsberg up on his offer.
According to an illegal FBI recording, powerful New Jersey mobster Ruggiero “Richie the Boot” Boiardo bragged to Chicago Outfit boss Sam Giancana that he had personally murdered Strollo.
We will likely never know the truth about what happened to Anthony Strollo.
Sources:
Hunt, Thomas. “Strollo, Antonio (1899-1962)” The American Mafia, 2021, https://mob-who.blogspot.com/2015/12/antonio-strollo-1899-1962.html
Scarpo, Ed. “Mob Hitman Who Likely Killed "Tony Bender" Dies.” Cosa Nostra News, 9 December 2014, https://www.cosanostranews.com/2014/12/mob-hitman-who-likely-killed-tony.html
“Machiavellian Mobsters Top 25 (#25 Anthony "Tony Bender" Strollo)” Youtube, uploaded by OC docs, 17 August 2023, https://www.youtube.com/watch?v=G7HG6bD_7eQ