Shooting death shatters a rare bond

It was a surprising bond.

Damien Perry was a 20-year-old member of the Castlegate Road gang, a group of about 30 young men who had terrorized Grove Hall in Roxbury in the 1990s, selling crack cocaine and occasionally shooting and killing those who got in their way. Nancy Gertner was the Yale-educated federal court judge presiding over his case.

But Perry was smart, polite, and eloquent, and Gertner instantly liked him. In 2000, she sentenced him to federal prison, but she would see him again and again after his release two years later -- sometimes for regular court appointments and other times because he just felt like dropping into her chambers for a visit.

Over the next seven years, they formed a rare relationship. He sent her letters from prison, told her about his girlfriend and his daughter, and she reviewed his resume for him when he was released. He wanted her to like him, told friends and lawyers how much he respected her, and when he quit his job or got in legal trouble, he worried about disappointing her.

When Perry, 28, was gunned down Saturday afternoon at Woodbine and Warren streets in Roxbury, Gertner was crushed.

"This was someone that we thought could make it," she said. "What a waste of a life. What a total waste of a life."

The bond that developed between Gertner and Perry was unusual in a court system where judges tend to see an endless train of society's ugliest problems and rarely make personal connections with defendants who often live in different worlds. Perry was black, the child of teen parents, and a high school dropout. Gertner is white, graduated from Barnard College, and received her law degree from Yale Law School. Like many judges, she has heard the defiance of defendants too tough to apologize and the tearful laments of the falsely contrite.

But in May 2000, when Perry, a stocky man with a left eye swollen shut from a shooting accident that left him partially blind, appeared in her courtroom, Gertner sensed something different about him. He played a smaller role in the gang, dealing drugs from doorways and alleyways around Columbia Road and Blue Hill Avenue.

He watched quietly as Gertner and the prosecutor, who wanted him sentenced to five years in prison, argued over the time he should get.

When she asked him if he had anything to say, he stood up and looked her in the eyes. He thanked her for pushing for a lighter sentence and apologized for his crimes. Other members of Castlegate had said little during their sentencings and stared at Gertner with defiance or no emotion. She was impressed by Perry's demeanor.

"His face would register with pain and embarrassment," she said. "He was very open. He was reflective."

She also sympathized with his difficult past.

His mother, who was 17 when he was born, turned to drug abuse and prostitution, and his father, who was 15, was too young to care for him.

The boy was raised by his maternal grandmother. He had a remarkable memory and did well in school. But he quickly found trouble.

At 15, he was convicted of trespassing and disorderly conduct. At 16, he and a friend were playing with a shotgun when it accidentally went off. Perry was shot in the head and lost his left eye.

Doctors could not remove the pieces of shot because they were too close to a major artery, so the fragments remained in his brain, often causing him headaches so painful he could not speak.

Less than a year later, he was convicted of armed robbery and dropped out of school. Then he joined Castlegate.

When he was released in 2002 he was sent to a halfway house, but he often violated his curfew, exasperating his lawyer, Walter B. Prince, who warned him he would not represent Perry if he messed up again.

"What was frustrating me is I would see in him all that talent and ability," Prince said. "And I was frustrated because I myself couldn't help him refocus it in a positive direction."

In December, after Perry had served about nine more months in prison for violating probation, he began working at his father's waste management company in Roxbury.

But Perry had a hard time following a regular work schedule, and often showed up late. He got into a car accident, took off two weeks to recuperate, and never returned to work, said his father, Jesse Jeter.

"It wasn't simple for him," said Jeter, 43. "Here's an intelligent, articulate young man who could never do the basics of society."

During his visits with Gertner, Perry would tell her he was having a hard time getting to job training seminars and meetings with mental health specialists.

"Kids who wind up in this web are dysfunctional to begin with," she said. "We're surprised when they come out dysfunctional, but the story with him was how do you come back into the modern world when you were barely equipped for it before?"

But Perry worried he was disappointing her, Jeter said.

"Often, I would hear him say when he did something not positive, 'Boy, Judge Gertner wouldn't be happy with me,' " he recalled.

She last saw him in April, when he and his new lawyer, Stylianus Sinnis, went to the courthouse to update her on his status.

Gertner invited the two into her chambers, and the rapport between the judge and the former convict was obvious, Sinnis recalled.

Perry wore a shirt with the face of late rapper Tupac Shakur emblazoned on it and when Gertner joked that she was proud she knew who that was, Perry grinned back.

"He generally appreciated the fact that she viewed him as a human being and as a person," Sinnis said.

Perry was supposed to return to her courtroom last week so Gertner could decide whether he should return to jail for a new set of parole violations -- losing his job and visiting Castlegate Road, where he had recently gone to visit his daughter.

But Sinnis said the appointment was postponed because Perry had found employment with his cousin's tow truck company.

Then someone shot Perry several times as he sat in a vehicle. Police said they have made no arrests and are investigating whether his shooting is connected to his days as a Castlegate member.

After he died, Gertner found notes she took during a December hearing when Perry had made one of his appearances in her courtroom for parole violations. She had written down what he said to her.

"I want to thank you, your Honor, for still believing in me," he told her that day. "I think that it's time that I practiced that myself, believing in myself."

Maria Cramer can be reached at mcramer@globe.com.