The man accused of shooting and killing a Malden mother by firing wildly at two men outside an Everett nightclub in 2015 pleaded not guilty to murder charges and will remain locked up on unrelated federal drug charges.

Henry “Jr” Del-Rio, 27, appeared in the dock before a Magistrate Clerk at Middlesex Superior Court in Woburn Thursday morning to plead not guilty on two separate charges arising from the same 2015 incident. He was on loan from federal custody and would return to the hands of U.S. Marshals following his appearance in state court.

A Middlesex grand jury issued indictments the morning of Jan. 12, 2024, charging Del-Rio 8 ½ years after the fact with the first-degree murder of Ashlee “Penny” Berryman, a 21-year-old mother of a 3-year-old son, and with related firearms offenses.

Berryman was outside the Braza Grille nightclub in Everett a little before 1 a.m. on Aug. 13, 2015, following a concert there in which her boyfriend had performed when she was caught in what Middlesex District Attorney Marian Ryan described as a “hail of gunfire.”

On Thursday, prosecutor David Solet, the chief of the Middlesex DA’s Cold Case Homicide Unit, summarized the state’s allegations that resulted in the indictments handed down last week: That early morning, Del-Rio got into a verbal argument and then “raised a 40 caliber semi-automatic firearm and fired repeatedly at two men.”

The bullets went everywhere, he said. While some of the shots struck one of the men he intended to shoot, another “crossed the street and penetrated the front window of a pharmacy. Another bullet penetrated the roof of a passing motor vehicle going just above the motorist head. And the last bullet penetrated the back and heart of Ashley Berryman, age 21 killing her.”

Del-Rio is represented by defense attorney Ian Gold, who also represents him in the federal case in which Del-Rio was convicted alongside fellow members of the Everett “East Side Money Gang” on racketeering, firearms and drug distribution charges. He was sentenced to five years in prison, though a revocation of that sentenced is scheduled to be argued in federal court in Boston on the last day of this month.

He also has a felony money laundering conviction from Woburn Superior Court, according to Solet’s run-down of Del-Rio’s criminal history.

While Del-Rio is in federal custody, Solet asked Clerk Magistrate Daniel Flaherty to order Del-Rio be held without bail in state custody on the indictments in case anything changes in his federal case and he is released.

Flaherty agreed with that and issued no bail. He also provisionally impounded documents with the narrative of the alleged incident. The next scheduled hearing is Feb. 14 to be held on Zoom.

Henry “JR” Del-Rio, 27, as seen in a law enforcement affidavit in his federal case. (Courtesy / U.S. District Courts)