Miami-Dade County Judge Mindy Glazer noticed the familiar face from Nautilus Middle School, suspect Arthur Booth.
She asked if Booth, 49, had attended the school.
"Oh, my goodness! Oh, my goodness!" Booth exclaimed before breaking down in the court last Thursday.
"I'm sorry to see you here," Glazer told Booth. "I always wondered what happened to you sir," she said.
Glazer said "he was the nicest kid in middle school" and lamented the choices that led him to her courtroom.
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Booth's cousin, Melissa Miller, told the Local 10 station that Booth had the potential to do great things with his life, but that future was destroyed by drugs and crime.
She added that she believed Booth felt ashamed when he saw Glazer.
"It just brought back memories of how smart he was," Miller said, the station reported. "He was a scholar, well- rounded athlete, bilingual."
Glazer wished Booth well in turning his life around.
"Good luck to you sir. I hope you're able to come out of this okay and just lead a lawful life," the station reported.
According to NBC Miami, Booth was arrested on Monday by police in Hialeah while he was spotted driving a gold Honda Accord suspected to be tied to a home burglary.
When an officer tried to pull Booth over, he allegedly fled, launching a police pursuit. He reportedly ran stop signs and was involved in two accidents before fleeing on foot. He was arrested a short time later.