Pedersen’s mental-health evaluation from February describes him as an “intelligent, polite, well-spoken, funny, likeable young guy.” The report also notes that he exhibits narcissistic and antisocial traits. Our conversations and letters brim with poetry and literature, from Wordsworth to Styron. He says he’s anxious to gain access to music and television in prison, to watch Downton Abbey, the popular British costume drama. In one letter, he transcribed Yeats’s “The Song of Wandering Aengus” from memory and scrawled his own analysis in the margins—to be digested alongside his criticisms of “negrified” America.

Tough-on-crime proponents maintain that Pedersen’s original sentencing in 1997 and the correctional decisions afterward were appropriate. “Here’s the problem with all the stories,” says Steve Doell, the Measure 11 supporter who’s now president of Oregon’s Crime Victims United. “We focus so much on the criminal and their stories and their point of view. The academics would have you believe he was a really good guy who just happened to commit some armed robberies. We don’t live in Father Flanagan’s world, and this isn’t Boys Town. These violent teens need to be incarcerated and treated and corrected.”

“A guy like this was violent already and he would’ve been violent if we’d waited until he was 18 or later to send him to prison,” says Doug Harcleroad, an Oregon Anti-Crime Alliance policy adviser and former Lane County district attorney. “It’s about picking out the ones who can change and the ones who can’t. I believe he can’t.” Harcleroad adds that violent crime in the state has dropped by more than 50 percent since Measure 11 became law. (He also acknowledges that this decrease may involve myriad factors, like the passing of the crack-cocaine epidemic and the aging of baby boomers.)

Meanwhile, Oregon politicians are beginning to reconsider Measure 11. Last year, a commission appointed by Governor John Kitzhaber recommended overhauling sentencing laws—largely to save money—and Kitzhaber and legislative leaders appear likely to consider some kind of reform in the 2013 session. The new head of the state’s billion-dollar corrections department, Colette Peters, was appointed in part because of her success in improving the Oregon Youth Authority.

Pedersen insists that he acted independently. At his sentencing hearing in March, he repeatedly told the court that he asked for no leniency. Speculation about alternate outcomes would be just that. But the question remains whether the system aided public safety in his case. “Do you feel safer having these kids get out after many years of company with shady adult prisoners, or having the kid get out sooner but with appropriate services and better company?” says the National Center for Juvenile Justice’s Melissa Sickmund. “It would be great if the justice system had a mind-set like medicine: first, do no harm.”