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Episode · May 20, 2026 · 1 hr 39 min

OxyContin, Graffiti, and a Second Chance

with J-Mac

Jason "J-Mac" McDonald is a Boston-area artist and recovery worker who rebuilt his life after years of opioid addiction.

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“I'm trying to get everyone to lean into what the [ __ ] they really like.”
Jason "J-Mac" McDonald

Summary

Jason "J-Mac" McDonald describes moving around Boston as a kid and finding identity in graffiti, hip-hop, and street life. Tagging and shoplifting grew into drug use, OxyContin, heroin, and years of addiction. He talks about the fear beneath his anger, overdose deaths around him, and his first attempts at sobriety.

A first stay in sober housing was followed by an arrest for graffiti and a court-stipulated rehab program. McDonald says he took recovery seriously at 25 and stayed sober for eight and a half years before relapsing in 2013. He returned to recovery after his friend Greg died in 2016. Today, he works in recovery, speaks in jails and treatment centers, and turns his graffiti background into paid murals, canvases, and custom art. Ken and McDonald discuss how helping others can give a person purpose without erasing the past.

Show notes

Jason "J-Mac" McDonald grew up moving between Malden, Medford, Chelsea, East Boston, and Revere.

Bullied, angry, and constantly trying to fit in, he found identity in graffiti, hip-hop, stealing, and eventually drugs. What started as tagging trains and shoplifting turned into OxyContin, heroin, violence, overdoses, and years of addiction that nearly killed him.

This conversation goes deep into Boston street culture in the late 90s and early 2000s – graffiti wars, robberies, fights, train yards, addiction, and the opioid epidemic that destroyed an entire generation.

But this isn't just a story about drugs.

It's about fear.Fear of not being enough.Fear of being judged.Fear of changing.

J-Mac talks openly about heroin addiction, relapse after eight years sober, losing friends to fentanyl, getting arrested while living in sober housing, and the moment that finally forced him to rebuild his life for good.

Today, he's sober, works in recovery helping addicts rebuild their lives, speaks in jails and treatment centers, and has turned his graffiti roots into a legitimate art career through murals, canvases, and custom work across New England.

This is one of the rawest Boston episodes we've done.

Read the transcript

Transcript

Made from YouTube's automatic captions and lightly corrected, so a few words and names may be off. Click a time to play the video from there.

Ken Rideout

All right, Jason McDonald, J-Mac, the artist, the most famous artist from Boston. My man, thanks for doing this. Appreciate you coming to Nashville.

Jason "J-Mac" McDonald

Thank you for having me. I'm glad I finally touched down here. I thought it was going to [ __ ] take forever.

Ken Rideout

Well, you're joining an illustrious uh roster of Bostononians from the Bean Shooter, Johnny Barts, and recently Chris Island. We got Chris Herren coming in next month. So, it's only appropriate that we get the uh top rated artist in Boston. Graffiti artist initially, right?

Jason "J-Mac" McDonald

Yeah. It started off as a graffiti writer before I was even an artist, just tagging stuff because of the freedom that I had with, you know, not much parental, you know, um, guidance. So, I just was tagging stuff when I was a kid just for to rebel and had no idea it would turn into this. That's funny because if [ __ ] I see someone writing on the wall or a or anything that isn't like appropriate to be writing on, I'm like, "What are you doing?" So, that must have been hard.

Ken Rideout

Did you get arrested?

Jason "J-Mac" McDonald

Yeah, I caught some cases, but I uh I got really good at a young age, so most of my stories are of getting away.

Ken Rideout

Do you know an artist called Eric Hayes? H A Z E.

Jason "J-Mac" McDonald

Oh, from New York.

Ken Rideout

Yeah. Yeah. Yeah. He started out as a graffiti guy and then moved into fine art and now he's like a legitimate like selling paintings for like hundreds of thousand dollars. And he participates in an art show every year in Brooklyn. I think it's in LA too called Beyond the Streets where street artists like uh Shepherd F

Key takeaways

  • A search for identity can turn creative outlets into crime or drug use when acceptance becomes the goal.
  • Fear of being judged and fear of change can keep addiction going.
  • A relapse does not erase years of sobriety, but it calls for renewed honesty and support.
  • Recovery can include practical work, family, treatment, and service to others.
  • Graffiti skills can become a legitimate livelihood through murals, canvases, and custom work.

Nowhere to Hide

A weekly letter from Ken Rideout about doing the uncomfortable part, and the reasons we use to avoid it.

It starts with 3 Days, 3 Hard Things: one short story from Ken and one hard thing to do, every day for three days. Then one letter a week.