Anthony Strollo – A Reputation for Switching Sides

Anthony Strollo, most notably known as Tony Bender, was born June 18, 1899 in New York City. He had two brothers, Emilio and Dominick. His playground as a young man was Manhattan, where he worked as bootlegger and enforcer for Joe Masseria.

Early in his mafia career Strollo earned a reputation for switching sides when it appeared he might be on the losing end.

Anthony “Tony Bender” Strollo was born on June 18, 1899, in New York City, alongside his two brothers, Emilio and Dominick. Growing up in Manhattan, Strollo initially made his mark as a bootlegger and enforcer for Joe Masseria, navigating the perilous waters of the city’s underworld. His early days in the mafia showcased his knack for survival, often by shifting allegiances to the most promising side. According to Carl Sifakis in “The Mafia Encyclopedia,” Strollo’s loyalty was a commodity, always available to the highest bidder, earning him a reputation for adaptability reminiscent of a chameleon.

His strategic side-switching was notably evident during the Castellammarese War. Sensing Joe Masseria’s impending defeat, Strollo aligned with Salvatore Maranzano, participating in the orchestration of numerous murders as Maranzano’s capo. However, the tables turned swiftly after Maranzano’s assassination by the Luciano crime family, propelling Strollo into a capo position under Lucky Luciano and his underboss, Vito Genovese. Strollo and Genovese developed a close bond, highlighted by Genovese serving as the best man at Strollo’s wedding.

Under Luciano’s leadership, the crime family soared to unprecedented heights, with Strollo amassing significant power through control over the Greenwich crew and major illegal gambling operations in Lower Manhattan. Yet, Luciano’s 1936 conviction marked the beginning of tumultuous times for Strollo. The landscape shifted dramatically when Genovese, facing a murder indictment, fled to Italy, leaving Strollo to fend for himself amidst a power struggle. Frank Costello’s rise as acting boss and Willie Moretti as underboss marginalized Strollo, stripping him of his rackets and influence.

After nearly a decade, Genovese returned from Italy, acquitted and reinstated into the Costello crime family, reclaiming the Greenwich gambling operations. Strollo, once again by Genovese’s side, played a pivotal role in their strategy to usurp Costello. The duo’s efforts culminated in a botched assassination attempt on Costello in 1957, orchestrated by Strollo but executed poorly by Vincent Gigante, resulting in Costello’s survival but subsequent relinquishment of power to Genovese.

In the late 1950s, Strollo continued orchestrating murders for Genovese, including the setup of his best friend, Little Augie Pisano. Despite Genovese’s ruthless rise to power and the creation of numerous enemies, it was his involvement in drug trafficking that ultimately led to his downfall. A coalition including Carlo Gambino, Meyer Lansky, Frank Costello, and Lucky Luciano, with Strollo’s aid, set Genovese up for arrest and a long prison term.

Genovese’s imprisonment didn’t halt his influence or his quest for retribution. Convinced of Strollo’s betrayal, Genovese orchestrated Strollo’s disappearance. On April 8, 1962, Strollo left his home without a topcoat, dismissing his wife’s concerns about the chilly weather, saying, “I’m only going out for a few minutes.” That brief exit marked the last time he was seen, culminating his complex narrative within the mafia’s treacherous echelons.

Carl Sifakis writes in The Mafia Encyclopedia, “Within the councils of the underworld it was no secret that Bender’s loyalty was always for sale to the highest bidder. He changed colors and sides like a chameleon.”

During the Castellammarese War when it was clear that Masseria was going to lose the war, Strollo aligned himself with Maranzano. As a capo to Maranzano, Strollo took part in the planning of several murders.

After Maranzano was murdered by the Luciano crime family, Strollo became a capo for Luciano and his underboss Vito Genovese.  Genovese and Strollo became close friends, with Genovese standing up as best man in Strollo’s wedding.

For a number of years the Luciano crime family was the most powerful family in New York. Strollo gained considerable power as well having control over the Greenwich crew and major illegal gambling in Lower Manhattan. It wasn’t until things changed in 1936 with Luciano’s conviction that the good life for Strollo would begin to unravel. Shortly after Luciano was imprisoned for what appeared to be the rest of his life, his close friend and new acting boss, Vito Genovese was indicted for murder.

Having no choice Genovese fled the United States for Italy leaving Strollo to “hold things together”. But it was not to be. Genovses’s chief rival Frank Costello pushed Strollo aside and appointed himself the acting boss, and Willie Moretti as his underboss. Strollo maintained a position in the family but with virtually no power. He was also stripped of his Greenwich rackets.

Genovese fought extradition from Italy to the United States for nearly 9 years. In 1946 Genovese returned from Italy having beat the indictment and was allowed back into the Costello crime family as a capo and given the Greenwich gambling rackets once controlled by Strollo and most recently the deported Joe Adonis.

For nearly ten years Genovese and Strollo worked the Greenwich rackets waiting for their time to take back the family from Costello. During that time, Strollo was the mastermind behind several murders on behalf of Genovese’s methodical march to taking over the family from Costello.

Costello was released from prison in 1957 and shortly after Genovese made the move to take control of the Costello family. He enlisted Strollo to set up the murder like he has several times before.

On May 2, 1957 Strollo met Costello at Chandler’s restaurant for an early dinner. During dinner he learned of Costello’s plans for later in the day consisting of several meetings later in the night.

When Costello was walking to the elevator in the lobby of his Manhattan apartment building he was shot in the head by Genovese gunman Vincent Gigante. Unfortunately, Gigante tipped Costello off to the assassination attempt by yelling, “This is for you Frank, prior to pulling the trigger. Costello reacted to the scream by turning his head slightly causing the bullet to graze his head. He fell to the ground and Gigante fled thinking he murdered Costello. Though he survived the murder attempt, Costello immediately stepped down as boss of the Costello crime family relinquishing control to Genovese.

In 1959 Strollo continued to set up murders for Genovese. One day he learned that “Genovese had marked his best friend, Little Augie Pisano, for murder- even Genovese was tenderhearted enough originally to try not to involve Bender-Bender cheerfully volunteered to set up the hit. He broke bread with Little Augie in a Manhattan restaurant while gunmen took up positions in Little Augie’s car to shoot him after he left.”

Through the years, Genovese used murder to take what he needed and created several enemies as he did. Eventually a conspiracy grew to finally end Genovese’s ruthless pursuit to the top of the mafia commission and it included his most trusted confidant, Anthony Strollo.

A secret meeting was held with Gambino boss Carlo Gambino, Meyer Lansky, Frank Costello, and Lucky Luciano who hatched a plan to use Genovese’s drug trafficking as a way to end his reign. Strollo aligned himself with the men and helped set Genovese up that would eventually send him to prison for the rest of his life.

Though Genovese was sent to prison on a fifteen year term, he continued to control the family. With time on his hands Genovese used it to figure out how he was captured. He suspected he was set up, but was unsure of how or whom was involved.

At some point, Genovese concluded that Strollo was part of the plot to set him up. After all it was Strollo was stressed to Genovese to give himself up because he would likely only get a short sentence. It was this knowledge that helped Genovese come to the conclusion that his old friend was part of the plot. As boss of the family, Genovese had the means to have Strollo killed and put the wheels in motion.

Sifakis wrote, “On the morning of April 8, 1962, Bender left his home. His wife told him, “You better put on your topcoat. It’s chilly.”

Bender demurred. “I’m only going out for a few minutes…””

He walked down the sidewalk from his home and was never seen again.