Riches To Rags To Riches: Profile Of Longtime Bonanno Mobster Nicky Cigars Santora

Nicholas (Nicky Cigars) Santora spent decades of his life in the Mob and had the criminal record to show for it, having been arrested roughly two-dozen times, with a rap sheet dating back to 1966.

A prosecutor once noted how Santora had an "extensive, serious, substantial criminal record.”

He was a mobster to his core, a second-generation wiseguy. (His father, Modesto, was allegedly a Colombo soldier.) Made in the 1970s, he gained unwanted recognition in the early 1980s when he was caught up in the Donnie Brasco fiasco. For a time he was a force to be reckoned with, rising to underboss under Vincent (Vinny Gorgeous) Basciano. Still, Santora had mixed luck. Joseph Massino wasn't a fan. After the Last Don flipped, he recorded himself calling Santora a brokester while in a rigged conversation with Basciano.

He "ain't got any money," Massino griped. Santora would "borrow from people" but he "forgets to pay."

That argument doesn't appear to have held water later in life. Or, at the very least, it seemed that Santora didn't need to borrow money anyway...

Running Multimillion-Dollar Racket 
When arrested by federal agents in 2012, Santora was living in Deer Park, Long Island. He was hit with a barrage by law enforcement officials. In 2013, he copped to a federal extortion charge in Brooklyn and was sentenced to 20 months in prison. He was serving that sentence in the Federal Correctional Institution in Loretto, Pa., when he was indicted in 2013, along with his alleged crew, by Manhattan DA Cyrus Vance for running a racketeering entity that included a $9 million online Costa Rican-based sports betting operation.

Santora and his crew --they were rounded up in July 2013 and were "armed to the teeth," prosecutors charged -- also had been recorded planning to sell hundreds of thousands of pills for at least $5 a pop. They also were charged with running loansharking and book-making operations that included the savvy proviso of a "captured market"  as well, thanks to the president and shop steward of a union that represents truck drivers and parking lot and gas station workers. The crew helped elect the union officials for their help facilitating loans and bets with the union's rank and file.

Law enforcement officials, then, held Santora up as an example of the Mafia's resurgence in the U.S., after the FBI had downsized its organized crime division to enlarge its terrorism focus. Santora also was portrayed as someone who'd evolved into almost a new breed of 21st century gangster.

Said Vance: “The charges against this Bonanno crew and their captain, Nicholas Santora, make clear that traditional organized crime refuses to go away. ...."

Police Commissioner Raymond W. Kelly said: “The organized crime activity described in the indictment is as old as the Bonanno crime family, and as relatively new as online betting and trafficking in highly addictive Oxycodone. Either way, it’s corrosive to society and lines the pockets of those who use or sanction violence to enrich themselves....."

Still he didn't fit the stereotype --no one ever does--and something faintly comical occasionally hovered about Santora. (Since we're not writing psycho-babble, we'll refrain from speculation and judgment calls.)

In a 2014 courtroom proceeding, recordings were played in which he told Vito Badamo, who he allegedly was grooming to take over his crew, to quit "acting like a clown."

"You gotta start conducting yourself in a certain way, you understand?"

"When I leave, you're going to take over this neighborhood — you got to know how, what the f--k you're doing.

"Acting like a clown — those days are over. You gotta act like you're supposed to act. You understand?" He seemed to have too much of a  familiarity with clowning.

And, for all his talk about acting appropriately, etc., Santora once showed up at a sitdown clutching a pillow. His role at the sitdown -- his reason for attending --was to let someone know that their life was on the line.

And those hundreds of thousands of pills the crew was preparing to unload, allegedly? The stash included oxycodone painkillers, yes, but it also included other types of pills, namely Cialis and Viagra, meds to treat erectile dysfunction.

The Brasco case exploded in November 1981, for some wiseguys, quite literally, when the first indictment came down detailing how, for the first time ever, the FBI had slipped two undercover agents inside the Mafia. (More than 100 mobsters were ultimately hit to some extent by the six-year probe.) On November 23, 1981, in U.S. District Court in Manhattan, Santora, Dominick Napolitano, Benjamin Ruggiero, John Cerasani, James Episcopia, and Antonio Tomasulo were indicted on charges of conspiring to murder three Bonanno capos, Alphonse (Sonny Red). Indelicato, Phillip (Phil Lucky) Giaccone, and Dominic (Big Trin) Trinchera. The bullet-riddled body of Sonny Red had been found in Ozone Park, Queens. Giaccone and Trinchera -- and also Sonny Black Napolitano -- were all missing, though believed dead.

In his 1982 testimony, Joseph Pistone told of daily life and crime inside a New York crime family. Eventually, he discussed the murders that were the centerpiece of the case: the 1981 triple slayings of three Bonanno captains.

Santora, Pistone testified, had told him how Trinchera had been blown apart with a shotgun.

“Nicky said you should have seen when they shot him—fifty pounds of his stomach went flying,” Pistone said.

An arrest complaint for Benjamin Ruggiero described the three capos as insurgents who'd attempted to wrest control of the crime family from boss Philip (Rusty) Rastelli, making that complaint the first public reference to the inner tumult that had convulsed the Bonanno family after the murder of Carmine Galante, which had actually served to unite the crime family's factions, though only temporarily.

Santora and the others also were charged with plotting a fourth murder, distributing narcotics, and running an illegal gambling business. The indictment also included an attempt to rob the Manhattan apartment of Princess Ashraf Pahlevi, the sister of the late Shah of Iran, in June 1980. The plot was allegedly foiled by bodyguards.

In testimony at the 2016 trial, James “Louie” Tartaglione talked about his longtime former friend. “I was there when (Nicky  Cigars) was inducted. I was at the ceremony.”

He added, “Sal (Vitale) gave him things to be concerned about, and then we all held hands and said a prayer.” He's apparently talking about getting made...

Tartaglione, a onetime Bonanno family captain, became a government witness in 2003. 

Santora, Ernest Aiello, Vito Badamo, and Anthony Santoro were charged with enterprise corruption. Five others copped plea deals.

The bulk of the evidence presented by prosecutors consisted of recordings of telephone calls and from a bug planted inside Santora's car for a period of roughly  10 months.

Santora, prosecutors charged, ran a tight, hierarchical organization, collecting a portion of all the proceeds from criminal activities in which his underlings were involved and settling disputes.

The defense claimed overzealous detectives in the NYPD's organized crime unit cooked up the case.

“The cops got it in their heads the Bonanno organized crime family was involved,” one  lawyer said. “They were like children who couldn’t accept a puzzle piece not fitting, so they smashed it until it was close enough.”

Shortly before the mistrial was declared, Santora's relatives noted that he was denied bail for a non-violent crime and railroaded for being Italian.

"They were targeted because they're Italians," the relative added. "I really believe that. Nobody got hurt. Nobody was killed. That mafia doesn't exist anymore.

"They gave him a bad deal. They stomped all over his rights."