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Delaware-Based Folk Journeyman John Flynn Finds a New Calling

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The celebrated singer/songwriter is now helping those behind bars.

Photographs by Jim Graham

John Flynn knows that his music career isn’t what it used to be. This is a guy, mind you, who’s played with Willie Nelson and spent time churning out songs in Nashville in the wake of disco’s demise. But the Wilmington-based artist isn’t playing live so much these days. And though he’s been working on a CD, he isn’t recording as frequently.

Some people get stage fright. Not Flynn. He feels more comfortable singing in front of an audience than he does talking to people. He’s had a guitar in his hands since he was 11 years old. Considering he’s now 63, that’s a long time. But these days, bars, clubs and other venues aren’t where Flynn is needed. This past spring, when COVID-19 kept most of us in lockdown at home, Flynn couldn’t keep his mind off the guys he knew who were literally in jail—and how the work he’s done for the past 15 years was being interrupted by the pandemic.

It might seem like a significant departure for a folk singer to be spending so much time among the incarcerated at Sussex Correctional Facility in Georgetown, Del. Flynn doesn’t agree. When he was younger, he second-guessed himself—a lot. In 2005, he didn’t think twice about taking over as executive director of New Beginnings-Next Step, a peer support group for prisoners transitioning back to life on the outside. It’s the sister organization of New Beginnings, which was founded in the early 1990s by Brother David Schlatter, a Catholic chaplain at Wilmington’s maximum-security Howard R. Young Correctional Institution. “I’m trying to live closer to what my heart is telling me, whether I’m at a microphone or in a prison chapel,” says Flynn. “The distinctions between my musical life and my personal life have disappeared.”

The core concepts of New Beginnings-Next Step aren’t that complicated: Show up, open up, listen up. It’s hard work—emotionally grueling really. In the process, Flynn’s efforts have led to personal breakthroughs and positive outcomes for many. The meetings can be intense, and they bring a momentary respite to endless, often terrifying days.

Flynn understands that the men appreciate and respond to authenticity. When he talks about the armor they wear, he might as well be referring to himself. “My guitar may be my armor. I can walk up to the dragon, and I can be vulnerable and open my heart because I still have protection,” he says. “When I had to lay my guitar down, it brought a new level of naked for me.”

Flynn has engaged the help of others. One, Sandy Stefanowicz, taught Flynn drama at Delaware County, Pa.’s Ridley High School in the 1970s. Her tutelage later led to his role in the early 2000s TV show Hack. “I’ve seen John transition even more in recent years,” Stefanowicz says. “This has become his life’s work. He’s committed to bettering the lives of these men and helping them get ready to be released.”

In 2011, Flynn convinced Stefanowicz to come to Sussex to conduct a breathing exercise. Fourteen years later, she’s there every week. “At one meeting, one of the guys came up to me and said, ‘Please don’t feel afraid to come back here. It felt like we were out of prison,’” says Stefanowicz.

Flynn’s first guitar was a Yamaha six-string model his uncle gave it him after a stint in the Marine Corps. Flynn fooled around with it in high school, then used it to help pay the bills while at Temple University. He’d planned to play lacrosse at the Naval Academy, but he reversed field when he found out he couldn’t have his guitar on campus.

Flynn’s parents were “ambivalent” about his musical pursuits. But that didn’t stop “hootenannies” from breaking out around the kitchen table at the Flynn home in Ridley Park. Even as a teen, Flynn was looking for music with meaning. “I loved songs that
had a message and something to say,” he says. “I liked the ones that lifted people up.”

In the 1980s, Flynn moved to Nashville to find work as a songwriter and hone his skills. There, he met David Mallett, a famous writer of folk standards whose songs have been recorded by everybody from John Denver and Alison Krauss to the Muppets. Although Flynn had some success there, his style didn’t fit with the factory mentality in Music City, where musicians and lyricists would sit in rooms and crank out song after song in the hopes of creating a hit. “I need to let the song sleep,” says Flynn.

Flynn performs at Wilmington’s Baby Grand in 2009.

Nonetheless, he did play with the likes Nelson, Arlo Guthrie and Kris Kristofferson. The latter wrote liner notes for one of Flynn’s CDs, singing with him on several songs. When Kristofferson’s long-time guitarist, Stephen Bruton, died of cancer in 2009, he recited the lyrics to Flynn’s “Without You With Me” at the funeral.

Over the subsequent decades, Flynn recorded and performed in a variety of settings. After Hurricane Katrina in 2005, he was on the “Train to New Orleans Tour” that featured a now-legendary Tipitina’s performance by Nelson. Back home, he was a regular on Kathy O’Connell’s Kids Corner radio show on WXPN and sang “God Bless America” at Citizens Bank Park in Philadelphia after 9/11. He was also the last person to sing at Philly’s now-demolished Veterans Stadium.

Flynn could’ve done more, but he was committed to raising his four children. It meant some tough times when the money wasn’t coming in regularly. “People ask me all the time, ‘Should I do this?’” Flynn says about a career in music. “I say, ‘If people can talk you out of this, don’t do it.’ You need a real passion. I wish I could go back and remember walking off the stage after playing with Willie Nelson—or after helping a prisoner with a breakthrough—and tell myself not to sweat it so much.”

Though Sussex is his home base now, Flynn began working with prisoners as a lead inmate support group facilitator at Howard R. Young. At first, he felt like a substitute teacher. “I was so out of my depth,” he says, adding that he returned repeatedly, developing a rapport.

The New Beginnings-Next Step program is funded almost entirely by fans of Flynn’s music and his work in the prisons. There is a musical component to what Flynn does, but so much of it is listening, learning, sharing and supporting. “It continues to be an amazing lesson about what you can do when you just say, ‘Let’s do this,’” he says.

Flynn will keep coming back. And he’ll bring his guitar—because everyone needs some armor.

Visit johnflynn.net.