The 15-year-old, David Michaud, had been charged with murder. McDermott's father, a criminal defense lawyer, was going to represent him.
"I was doing some of the same things that this kid was doing in terms of skipping school, running around with friends at night, getting into a little minor trouble," the younger McDermott said.
Years after Joseph McDermott died in 2009 at the age of 75, McDermott flipped through the yellowed photo albums holding newspaper clippings of his father's days in court when he saw Michaud's face. He was now in his 40s, serving a life sentence for the 1983 murder.
The black-and-white photo flooded McDermott with memories of his father telling him to stay out of trouble, of his days working at the family firm while he was in law school, and the cases father and son, both lawyers, worked on together in later years.
"The greatest thing was to get my degree at Stetson and to practice with my dad," he said.
He wanted to take on his father's old case, 34 years after the elder McDermott tried to divert a juvenile from the electric chair. Michaud, he thought, had a chance of being resentenced under new Florida laws.
He sent a letter to the prison.
• • •
According to police records, this is what happened the night of June 30, 1983:
Michaud and a friend, Steven Medlin, were smoking marijuana and taking LSD. The 15-year-olds watched Return of the Jedi at the movie theater in Sunshine Mall in Clearwater.
Afterward, they wanted to visit a friend in Hudson, but were short on cash for a taxi. That's when they concocted the plan to break into Robert Ebeling's home. Medlin had cut the 79-year-old widower's lawn at his Largo house.
The boys climbed in through a bedroom window with a missing screen. In the darkness, Medlin knocked over a vacuum. Ebeling found them and confronted the teens.
They struggled with the elderly man as he collapsed on the bed. As Medlin pinned him to the mattress, Michaud wrapped his arm around Ebeling's neck. He grew limp, and the teens covered his body with a blanket. In a closet, they found about $400. They cut the telephone cords and left.
Two days later at a skating rink in Hudson, Michaud and Medlin were arrested.
• • •
In a recent interview, Michaud said he remembers the first time he met Joseph McDermott. The lawyer with the salt-and-pepper beard and a penchant for bubble gum shook the teen's hand.
Court records detail the elder McDermott's efforts to help his young client. He requested a psychologist's evaluation. He argued in motions that Michaud's confession should be dismissed because he was intoxicated at the time of the interrogation.
But when the Pinellas-Pasco State Attorney's Office sought the death penalty, McDermott told Michaud his best option was to plead guilty, the lawyer's son said. At the time, juveniles could be condemned to death row.
In February 1984, Michaud, then 16, pleaded guilty to burglary and murder and was sentenced to life in prison with the possibility of parole after 25 years.
"I went ahead and signed the paperwork and took the deal," Michaud said. "It was more a relief that okay, I can go to prison, do the things I need to do to change, to become a better person, get my act cleaned up. There was more of a sense of hope."
• • •
The first thing Michaud, 49, noticed about the recent letter was the name printed on the stationary: McDermott.
He assumed it was his old lawyer, but soon realized it was a son.
"I worried that he might resent me for his life sentence too because it was our firm that represented him," Frank McDermott said.
But Michaud wrote back. He accepted McDermott's offer to represent him pro bono.
McDermott wrote Michaud's motion for a resentencing in light of a wave of juvenile proceedings happening across the state. In 2012, the U.S. Supreme Court ruled that automatic life sentences for juveniles were unconstitutional because they violated Eighth Amendment protections against cruel and unusual punishment.
Under a new Florida law, a judge must consider several factors, including age at the time of the crime and potential for rehabilitation, before ruling that a juvenile deserves a life sentence, with a review after 25 years. If a life sentence isn't appropriate, the minimum penalty is 40 years.
But Michaud's case faces obstacles. He became eligible for parole after serving 25 years in prison and was given a release date of 2031. Medlin, who also got a life sentence, was released on parole in 2013.
In court records, the Pinellas-Pasco State Attorney's Office argues that Michaud is not entitled to relief because his parole date falls within his life expectancy. In 2031, he will be 64.
"The question right now is whether juveniles whose release date falls within their life expectancy — or who haven't had their release dates set yet — are also entitled to resentencing hearings," said Pinellas-Pasco courts spokesman Stephen Thompson. "Our judges would like clarity with these types of cases, and are awaiting a decision by the Florida Supreme Court."
Michaud was transferred from state prison to the Pinellas County Jail in January, where he waits for developments in his case. In prison, Michaud earned certificates for auto body detailing and painting. His last disciplinary report, for keeping other inmates' financial information, was six years ago.
"I want to give something back to my society," he said. "If I could take it all back, I could. But I know I can't."
For McDermott, representing Michaud is something he believes his father would have wanted.
"This is a chance to maybe get it right," he said. "And I think he's paid his debt to society."
Times staff researcher Caryn Baird contributed to this report. Contact Laura C. Morel at firstname.lastname@example.org. Follow @lauracmorel.