Shane Pryor was handcuffed and shackled before being taken to the hospital. How did he escape?

Seventeen-year-old Shane Pryor was handcuffed and shackled before being driven from the city’s juvenile detention center to a local hospital, law enforcement sources say, calling into question how he was able to break free of those restraints before escaping — and whether anyone helped him.

That has become a key part of the investigation into how Pryor, who is accused of killing a woman in 2020, escaped from the custody of juvenile jail staff on Wednesday afternoon, said the sources, who spoke on the condition of anonymity to discuss the ongoing investigation. And it comes as officials have zeroed in on at least one person they believe helped him: Michael Diggs, an 18-year-old suspected getaway driver who sources said Pryor met inside the juvenile jail a few years ago.

Diggs was charged Friday with escape, hindering a police investigation, criminal conspiracy, and related crimes, police said.

Pryor was being taken to the Children’s Hospital of Philadelphia just before noon Wednesday, for treatment of a hand injury when police say he emerged from the vehicle unshackled and without handcuffs. He then pushed past the two unarmed staffers and fled.

Within minutes, he approached a bystander, saying he had just been in a fight and needed to make a phone call, said Supervising Deputy U.S. Marshal Robert Clark. He then used the woman’s phone to call Diggs, Clark said, and by 12:30 p.m., Diggs had picked him up and driven him out of the University City area in a tan Ford Fusion.

Within the hour, Clark said, the two were spotted in the Olney section of the city. Video showed them near Godfrey Avenue and Mascher Street from 1:15 p.m. until about 2 p.m., when they then drove off together in the tan car.

About four hours later, police pulled Diggs over in that same car, but Pryor was no longer with him.

Law enforcement officials have declined to share specifics on whether Pryor’s escape was planned or if any jail staffers may have helped him, saying only that investigators are looking into all possible angles.

U.S. Marshals said that as of Friday afternoon, they believed Pryor was still in the city. The video of him in Olney on Wednesday afternoon remains the last known sighting, Clark said.

Anyone who aids Pryor will be charged, he said. Pryor is known to have connections in the Mayfair section of the city, and investigators have focused some of the search in that area, Clark said.

“Right now, we’re trying to shrink his world down, we’re trying to cut off his resources and cover every avenue of escape that he could have,” said Clark. “Remember, he’s only 17 years old, he’s been in jail the last three years. How many resources ... can he have?”

“I’m extremely confident we’re going to find him, it’s just a matter of when,” he said.

Detectives believe Pryor and Diggs met over a year ago inside the city’s Juvenile Justice Services Center, and have kept in touch since, sources said.

Pryor has been in custody since October 2020, when he was arrested at age 14 along with another teen and charged with killing 54-year-old Tanya Harris.

» READ MORE: Disturbing new photos inside Philly’s juvenile jail show kids sleeping on floors in crowded, filthy cells

Court records show that Diggs was arrested in June 2022 when he was 16, and charged with attempted murder, illegal gun possession, and related crimes after police accused him and three others of shooting two teens as they left Simon Gratz High School one afternoon.

But last year, Common Please Court Judge Lillian Ransom threw the case out after Diggs’ attorneys successfully argued that police and prosecutors did not have enough evidence tying Diggs to the shooting. Court records show that prosecutors did not appeal, and Diggs was released from custody in March 2023.

Young people accused of homicides are typically held in a separate wing of the juvenile jail, but one source said investigators believe the two met in a holding cell, where those in custody are typically held before being transported off site to court hearings or doctor’s appointments.

Pryor and 15-year-old Kiyan Williams were charged with murder after police said that on Oct. 10, the two teens met with Harris in an alleyway, paid her for sex, then shot her in the head. A passerby found Harris’ body hours later, leaning over a railing near 7400 Torresdale Ave.

According to the affidavit of probable cause for his arrest, Pryor told police he was in the alley but did not shoot Harris. Pryor’s mother has said her son has always maintained his innocence and that they intend to take the case to trial. She has encouraged her son to turn himself in.

Williams also remains in custody awaiting trial.

Pryor’s escape has again put the spotlight on potential failings of the city’s jails and prisons, and the longstanding issues within the juvenile detention center, which is run by the city’s Department of Human Services. It follows the breakouts of four adults from city prisons over the last year.

Pryor’s lawyer, Paul DiMaio, said he believes Pryor was fearful of facing adult prison, as he is just two weeks away from turning 18. He said he and his client had asked a judge to send his case back to juvenile court last month, but the request was denied — allowing the case to move forward through the adult system.

DiMaio said that may have led Pryor to lose hope and decide to flee.

Clark, of the U.S. Marshals, said Pryor’s escape would only exacerbate his legal troubles.

“He should be fighting his case in the courtroom,” he said, “and surrender to the nearest police officer immediately.”

Staff writer Rodrigo Torrejón contributed to this article.