When four men were charged this week in the brazen armed robberies of two Manhattan jewelers, their ages suggested it might not be their first encounter with the criminal justice system.
Among them, according to officials and court documents, the men have ties to the Genovese, Lucchese and Kansas City, Mo., crime families; a history of bank robberies, racketeering and killings; and a jailbreak reminiscent of a Hollywood movie.
The defendants are Vincent Cerchio, 69; Michael Sellick, 67; Frank DiPietro, 65; and Vincent Spagnuolo, 65. If convicted of the most serious charge, each faces the prospect of returning to prison for as long as 20 years for failing to do what many people their age have done: retire.
The U.S. attorney’s office for the Southern District of New York charged the four with stealing $2 million in diamonds and other gems at gunpoint while dressed as construction workers to blend in on busy streets. A fifth man, Samuel Sorce, 25, of Florham Park, N.J., is charged with being a getaway driver in one of the heists.
“The professional planning and execution of the robberies” reflect the older men’s “long histories of serious violent crime,” prosecutors said in a court filing. As evidence, the filing cites surveillance footage, call records, license plate readers, eyewitnesses and cellphone transmission data.
Mr. DiPietro’s lawyer, Mathew J. Mari, said his client was not guilty. Mr. DiPietro did work in construction, Mr. Mari said, had led an “exemplary life” in recent years and believed that he and the others had been arrested because of their résumés.
“He said, ‘They’re just trying to pin it on us because we’re career criminals,’” Mr. Mari said.
Organized crime has long been the province of older men. And with some activities that were traditional mob rackets, like sports betting, becoming legal, there may be fewer opportunities for young, would-be gangsters to commit the entry-level crimes that might make their reputations.
Elie Honig, a former top federal organized-crime prosecutor in Manhattan, cited several reasons for what he called the “perpetual graying” of the Mafia. For one thing, it takes years to climb the ranks; rarely is a member inducted, or “made,” before he is in his 50s. For another, Mr. Honig said: “There’s no such thing as retirement from the mob. They don’t have a pension plan.”
The advanced age of many gangsters often becomes a factor at sentencing hearings, when bids for leniency tend to rely heavily on litanies of medications, impairments, illnesses and other ravages of time.
When Mr. Honig prosecuted his first organized crime case in the early 2000s — the reputed Genovese boss Matthew Ianniello and a score of other defendants — the average age of those charged was well over 70. The scene at their booking featured walkers, wheelchairs and oxygen machines, he said.
Mr. DiPietro — born when “Gunsmoke” was the most popular show on television — and his fellow defendants made initial appearances on Tuesday in federal court in Manhattan, where a judge ordered that they be detained. They are scheduled to return to court next month.
The first robbery was on Madison Avenue, in a building where a jeweler operating from the penthouse stocks a street-level display case with pricey items each day, according to a criminal complaint.
On Jan. 3, Mr. Cerchio, Mr. DiPietro, Mr. Sellick and Mr. Spagnuolo traveled to the area of the building, the complaint says; several of them had scouted the site the day before.
Just before 10:30 a.m., the complaint says, Mr. DiPietro and Mr. Sellick, in masks, hats, jeans, sneakers and brightly colored, construction-style jackets, entered the lobby and confronted a worker who had just opened a safe.
“Give it to me,” Mr. DiPietro, brandishing a gun, ordered before grabbing a 73-carat necklace, a 17-carat pair of earrings and a six-carat ring and running off, the complaint says. Mr. Sellick told the worker to “get in the closet” and fled as well.
The second robbery, on May 20, involved a jewelry store on Elizabeth Street in Chinatown, according to a second complaint.
Mr. DiPietro and Mr. Sellick, wearing similar outfits, stormed into the shop soon after it opened, prosecutors say. This time, Mr. Sellick had the gun and ordered workers to the floor while Mr. DiPietro snatched up jewelry, prosecutors say.
The two fled first in a vehicle driven by the relatively fresh-faced Mr. Sorce, then in one driven by Mr. Spagnuolo, who prosecutors say was also a getaway driver in the first robbery.
Mr. Spagnuolo, of Monmouth Beach, N.J., is the only one of the four older men without a federal conviction, according to prosecutors. He pleaded guilty to manslaughter in state court in 1979 and was sentenced to 10 years in prison, records show. Later came two convictions on robbery-related charges.
Mr. DiPietro, of Red Bank, N.J., is also an admitted killer. In 1999, he pleaded guilty to fatally shooting a grand jury witness who had testified about a Lucchese-related drug conspiracy, court records show. The victim was found in a car in a remote area of Staten Island after being shot four times in the head. Mr. DiPietro was sentenced to 19 years in federal prison and released in 2016.
Mr. Cerchio’s federal record, prosecutors say, includes a 1997 indictment stemming from the murder of a fashion designer in his Upper West Side apartment in a “Lucchese armed robbery spree gone awry.” He pleaded guilty to a stolen goods charge and was sentenced to 27 months.
A sweeping set of federal indictments targeting New Jersey’s DeCavalcante crime family in 1999 named Mr. Cerchio as a Lucchese associate. The next year, he was sentenced to 51 months in prison after pleading guilty in a racketeering case involving DeCavalcante gangsters, prosecutors say. Later, in 2014, he pleaded guilty in a scheme to rob trucks of counterfeit cigarettes. Sentenced to 27 months, he was released in 2016, records show.
A lawyer for Mr. Cerchio, of Howard Beach, Queens, declined to comment on the latest allegations, as did a lawyer for Mr. Spagnuolo.
Mr. Sellick, of Franklin Square, N.Y., was first sentenced to federal prison in 1980 after pleading guilty to bank robbery, prosecutors say. In 1998, he pleaded guilty to five counts of armed bank robbery and was sentenced to another 19 years, records show. He was released in 2015.
Since then, his lawyer, Gerald J. McMahon, said, Mr. Sellick had worked steadily at a union job painting bridges and now earns $55 an hour. Mr. McMahon said Mr. Sellick was not guilty and that the case against him was one of “mistaken identity.”
Mr. Sellick has displayed a flair for drama in the past: Twice during a state prison stint sandwiched between his federal sentences he escaped from an upstate jail.
The first jailbreak, in 1979, resembled the plot of the film “Escape From Alcatraz,” which had just been released and was based on actual events at the famous island prison in San Francisco Bay.
In Mr. Sellick’s version, he and several others tore a light fixture from a cell wall, enlarged the resulting hole, crawled onto a catwalk, tore up a floor grating and slithered through 300 feet of plumbing pipes and electrical conduits to a gap in a wall left by construction work.
The Alcatraz fugitives were never found, dead or alive. Mr. Sellick, obviously, was.
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