The youngest of four men charged in the 2023 murder of Chicago police officer Aréanah Preston will remain in juvenile detention as he awaits trial, a Cook County judge ruled on Wednesday.

Jaylen Frazier, now 19, was only 16 years old when he was charged as an adult in the deadly shooting.

Preston, 24, was shot and killed outside her Avalon Park home in May of 2023, just after finishing her shift. She was just starting her career as a police officer, and was just days away from earning a master's degree from Loyola University.

Wednesday's hearing in Frazier's case was the first of multiple hearings in the next week for the four men charged with Preston's murder.

The courtroom was filled with Preston's family members, supporters, and fellow officers who showed up to watch yet another step in a long-awaited legal process.

Chicago Fraternal Order of Police president John Catanzara said the case is unusually complex.

"These processes are never easy. Some of these cases are a little more intricate. Having four offenders, this has made it probably one of the more complicated ones we've had in a long time," he said.

Frazier was escorted into court wearing a Juvenile Temporary Detention Center shirt and sweatpants. He has been housed in juvenile detention ever since he was charged when he was 16 years old.

A staff member testified Frazier had two rule violations in custody last year. Judge Adrienne Davis ruled Frazier will remain in juvenile detention while he awaits trial rather than be transferred to Cook County Jail.

Three other men also face murder charges in Preston's death – Jakwon Buchanan, 20, Joseph Brooks, 22, and Trevell Breeland, 22. All four face multiple felony charges, including first-degree murder, armed robbery, possession of a stolen vehicle, and burglary.

Police have said the four men tried to rob Preston, who was off duty but still in uniform, as she was just getting home from work in the 8100 block of South Blackstone Avenue on May 6, 2023. At least two of the suspects started shooting at Preston, who returned fire.

Investigators have said all four were also connected to multiple robberies and a car theft before killing Preston. All of them have lengthy juvenile records.

"It's torture on these families," Catanzara said.

Despite the emotional toll, families have been showing up — some wearing "Peace For Preston" sweatshirts – to witness the lengthy court battle, and not just for their own loved ones.

"Everybody's staying strong. It's encouraging to see other family members who have other cases in this court building to support each other," Catanzara said.

Buchanan and Breeland were due to appear in court on Thursday as they seek to have testimony from a firearms expert excluded from the trial.

Brooks was due back in court on Jan. 21 for a status hearing.

Trial dates have not yet been set for any of the four men charged with Preston's murder.