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A Youth Spent in Prison

Jeremy Armstrong, now a resident at a medium-security facility in Oshkosh, Wis.
Julia R. Buckley, NPR News /
Jeremy Armstrong, now a resident at a medium-security facility in Oshkosh, Wis.

In 1997, NPR's Robert Siegel first interviewed Jeremy Armstrong. Blond and fair-skinned, he was a conscientious, straight-A student at an inner-city Catholic school.

Armstrong had just turned 16 -- but he looked like a child in his one good suit, facing a jury that was to decide his fate. A few months earlier, he had murdered his father's roommate and drug dealer, a man named Robert Drury. He stood trial as an adult, even though he was just 15 at the time of the shooting.

He was accused of first-degree murder, under Wisconsin's new "get-tough" juvenile justice policies. But the jury acquitted Armstrong of that charge, finding him guilty instead of reckless homicide, which is a lesser offense.

Still, Armstrong didn't get off easy. He was sentenced to 20 years in an adult prison -- Wisconsin State Correctional Institution, 120 miles north of Milwaukee at Green Bay. Siegel followed the 1997 trial and sentencing, then checked in on Armstrong again in 2000 and 2002. Today, Armstrong is 21 years old. He was recently denied parole, but was allowed to move to a medium-security prison in Oshkosh.

"The step down from a maximum to a medium security prison is a grant of freedom unimaginable to people who have never been incarcerated," Siegel says. "Jeremy beams at the possibility of showing me not his cell, he says, but his room. There's a lock on the door -- but he has a key."

Armstrong is one of a first wave of young offenders who started doing adult time in the 1990s, as many states cracked down on crime. He does not deny that he shot his victim. Armstrong says he tried to rob Robert Drury, a man he said had threatened him physically and sexually. He claims he wanted Drury's money to pay the utility bill at his mother's house, where the power had been turned off.

He used a gun only to threaten, he said -- but when Drury mocked him and lunged at him, Armstrong fired. At his trial, the prosecution called his crime premeditated. Armstrong says the shooting was impulsive.

Before the shooting, Armstrong lived a double life, bouncing between the crack house where his father lived and the darkened home that his methadone-addicted mother shared with her drug-abusing boyfriend. But the teenager also never missed a day of classes at Milwaukee's Messmer High School.

Those studious habits are still in evidence in Armstrong's cell. "On a small desk, Jeremy keeps his books, including a large dictionary, a thesaurus, a volume of Pablo Neruda he has yet to start," Siegel says. "He is a reader... he takes college English correspondence courses and is doing Shakespeare's tragedies this term."

Being denied parole last summer was a big blow. "It took about eight minutes, and they gave me a deferment -- and I see them again in 2005," he tells Siegel. "When it happened, (I felt) more shock then anger. I wasted all this time and effort. Not really wasted -- postponed three years."

Armstrong's goals for the coming year are to read 50 books, write 1,000 letters -- and improve his left-handed basketball dribble.

If Armstrong had been sentenced as a juvenile, he would have spent about three years behind bars in a youth facility and would be a free man right now. He says he tries not to think about what he could have made of those lost years. "It's hard to go back and rebuild what could have been," he tells Siegel. "I ate myself up for the first two years just wondering what could have been.

"I can't take away what Green Bay did to me -- I can't take away all the things I seen since then. I don't know what I would have turned out as..."

Copyright 2022 NPR. To see more, visit https://www.npr.org.

Robert Siegel
Prior to his retirement, Robert Siegel was the senior host of NPR's award-winning evening newsmagazine All Things Considered. With 40 years of experience working in radio news, Siegel hosted the country's most-listened-to, afternoon-drive-time news radio program and reported on stories and happenings all over the globe, and reported from a variety of locations across Europe, the Middle East, North Africa, and Asia. He signed off in his final broadcast of All Things Considered on January 5, 2018.