Judge Raymond Myles dispensed tough love, justice from bench

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Cook County Associate Judge Raymond Myles | Cook County Circuit Court photo

The scene in Room 204 when Judge Raymond Myles was holding court was unusual for the Leighton Criminal Courthouse.

The morning call started at 9 a.m. — sharp — and the docket was filled with “youthful offenders,” defendants in their teens to late 20s, convicted of minor charges and assigned to a strict black-robed paterfamilias who believed strongly it was his judicial duty to steer his charges to a better life.

Myles doled out advice and tough love from the bench, monitoring probation but also linking defendants to jobs and education.

The 66-year-old, who served on the bench in Room 204 for seven years, was gunned down Monday at his South Side home while attempting to disrupt a robbery of a female friend.

With Myles behind the bench, the jury box was set aside for late arrivals, who were sentenced immediately by Myles to write punitive “lines” on pages pinned to a clipboard: “Judge Myles, I promise I will not be late to court,” anywhere from 500 to 7,000 times. Anyone who didn’t finish before their case was called was required to bring the completed pages to their next court date. A probation officer, or Myles himself, would check each line for grammar and spelling.

Myles kept a stash of collared shirts for anyone who arrived without one. On weekends, he’d sometimes launder the wardrobe himself. One defendant, who confessed he never wore ties to court because he didn’t own any, received a bag of neckties taken from Myles closet at his next court date.

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When defendants learned why Myles was not on the bench Monday, several broke into tears, said Probation Officer Colleen O’Halleran-Foley, who, like most of staff in Room 204, had worked with Myles since he took over the youth call in 2007.

“I don’t know what’s going to happen,” said Willie Nesbitt, 21, who was waiting for his case to be called Thursday morning.

Nesbitt had been on probation under Myles’ supervision since 2014, after picking up a series of minor criminal charges in his late teens. Nesbitt recently had another drug possession charge in what he insists is a case of mistaken identity — he had pleaded not guilty — and he was confident that Myles believed him after seeing him in court on a near monthly basis for more than three years.

During his time under Myles’ supervision, Nesbitt had quit smoking weed, finished high school and landed a job — all with help and encouragement from the judge. When Nesbitt picked up his latest charge, Myles had put him on house arrest.

“He seen I was catching cases, and he didn’t want me out. I understood that,” Nesbitt said as he waited for his case to be called. With a substitute judge on the bench, his case was continued.

“If it wasn’t for [Myles] I never would have got my diploma, to be honest,” Nesbitt said. “He really was trying to help everybody.”

Myles always added educational requirements to his probation, hectoring his charges to get a high school diploma or GED, said Andrew Joslin, a sheriff’s deputy who worked in Myles’ court.

While jail time was always the stick looming behind Myles’ cajoling, the judge went out of his way to keep defendants out, where they could work or go to school.

“He really liked that he could actually make a difference,” Joslin said. “He didn’t want to send anyone to jail or prison.”

After his first year on the bench in Room 204, Myles began an annual tradition: a courtroom graduation party for anyone on his docket who had gotten a diploma or GED. As many as a dozen defendants would show up, many making the trip to the court house even though they no longer were required to do so by a probation officer.

Myles would even go to high school graduations to see his defendants get their diplomas in person, sometimes years after the last time he had seen them in court.

“Some of them, not all, would say things like, ‘You are the only person that cared enough about me to put this kind of time and effort into me,’ ” Deputy Patrice Scott recalled.

Smaller gestures made an impression on Myles’ defendants, and his courtroom staff, O’Halleran-Foley said.

When defendants finished probation, Myles would rise from his seat, lean over his desk and shake hands with the defendant, said O’Halleran-Foley, who has worked in courtrooms for 20 years.

“It seems like a little thing, but you just don’t see that from a judge, really. They sign the paperwork and say ‘good luck.’ He’d congratulate them and shake their hand,” she said. “For some of these guys, even with [Myles] pushing, they never finish school. This might be the only graduation they get, and the only time a judge would ever shake their hand.”

Myles had an elephantine memory for names and personal details, said Laura Moffett, his longtime clerk. He remembered whether defendants had children or ailing relatives, and asked about them— often reminding them that they needed to succeed to make a better life for their loved ones.

Myles’ compassion extended to his courtroom staff. Joslin recalled that Myles came to his mother’s funeral, and even gave a eulogy.

The mood in Room 204 on Thursday morning was somber. The usual slate of defendants lined up, their cases continued by a substitute judge. The pile of collared shirts sat untouched, as a stream of recovering drug users and young offenders walked into court in T-shirts and jackets — infractions that Myles might have punished with a few hundred lines of apology. Nesbitt’s case was continued for another month. He told a reporter he hopes to become an engineer and design cars.

At noon, Joshua Smith, the man charged with driving the getaway car for the man who shot Myles, would appear in a courtroom downstairs for a bond hearing. Moffett, Scott and Joslin would stand along the wall of the courtroom, listening intently as a prosecutor read off an account of Myles’ death. Smith would be ordered held without bail. The gunman who shot Myles down, and wounded a female friend of Myles’, remains at large.

After the hearing, Joslin, Moffett and Scott huddled outside the courtroom, Joslin’s arms draped over Moffett and Scott’s shoulders as the two women cried.

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