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.