OxyContin, Graffiti, and a Second Chance | J-Mac

OxyContin, Graffiti, and a Second Chance | J-Mac

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. Thank you to our sponsors Ketone-IQ: ⁠ketone.com/rideout Code “RIDEOUT” Timeline: timeline.com/rideout Code "RIDEOUT" Ken’s book now available here: https://www.theothersideofhard.com/ Chapters (00:00) Meet J Mac (00:28) From Graffiti to Fine Art (02:37) Boston Roots and Opioids (04:19) Fear and Moving Around (06:50) Graffiti Alter Ego (08:47) Sponsor Break (09:37) Seventh Grade Heist Story (15:10) Sneakers and Peer Pressure (17:33) Haters and Self Belief (19:22) Recovery and Connection (24:02) High School Riot and Dad (28:16) First Opiates and Creativity (30:43) Hustles and Shoplifting (33:01) Boosting and Getaways (33:54) Graffiti Life and High Spots (34:16) Sticker Swap Paint Hustle (35:46) Recovery vs Old Habits (36:07) Mitochondria Supplement Ad (37:39) Oxy Takes Over (38:49) Cross Out Wars Explained (40:17) Mall Fight and Aftermath (42:33) Identity Beyond Graffiti (43:25) Relapse and Heroin Shift (46:13) First Heroin and Needles (49:18) Overdoses and Saving Friends (53:57) Fentanyl Changes Everything (01:00:47) Choosing Recovery and Detox (01:02:59) Family Intervention and First Sobriety (01:05:57) Secret Drinking Spiral (01:07:03) Halloween Rooftop Bust (01:08:14) Barrel Hideout Arrest (01:11:21) Court Cases Wake Up (01:12:29) East Boston Rehab Reset (01:14:38) 2013 Relapse Reality (01:17:18) Greg's Death Turning Point (01:20:20) Helping Others Through Barbering (01:22:43) Building an Art Career (01:31:17) Speaking and Jail Outreach (01:36:12) Final Recovery Message Learn more about your ad choices. Visit megaphone.fm/adchoices

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Brutal Hits, Broken Bodies & the Business of Football | Bernard Pollard

Brutal Hits, Broken Bodies & the Business of Football | Bernard Pollard

Bernard Pollard earned a reputation as one of the NFL’s most feared hitters — and became known throughout New England as the “Patriot Killer.” In this episode, Bernard sits down with Ken Rideout to t...

26 Elo 1h 58min

The Cop Who Went to Prison for 19 Years | Kent McGowen

The Cop Who Went to Prison for 19 Years | Kent McGowen

Kent McGowen spent years enforcing the law. Then he spent nearly two decades behind bars. Kent is a former Houston police officer and Harris County deputy who was convicted of murder after fatally sh...

21 Elo 3h 6min

The Wall Street Executive Who Had Everything—Except Peace | James “Jet” Davies

The Wall Street Executive Who Had Everything—Except Peace | James “Jet” Davies

James “Jet” Davies spent more than two decades inside high finance, eventually becoming CEO of Deutsche Bank’s broker-dealer for the Americas. But behind the titles, money, and success was a life that...

19 Elo 2h

From Small-Town Kid to Everest, Equinox & IRONMAN CEO | Scott DeRue

From Small-Town Kid to Everest, Equinox & IRONMAN CEO | Scott DeRue

Scott DeRue has spent his life creating experiences that push people beyond what they thought was possible. Ken sits down with his longtime friend and current CEO of The IRONMAN Group to talk about g...

14 Elo 1h 41min

Jail, Navy SEALs, Fentanyl & the French Foreign Legion | Taylor Cavanaugh

Jail, Navy SEALs, Fentanyl & the French Foreign Legion | Taylor Cavanaugh

Taylor Cavanaugh’s life has been a cycle of achievement, self-destruction, and rebuilding. Before becoming a Navy SEAL, Taylor had already been expelled from school, arrested repeatedly, survived a v...

12 Elo 2h 26min

Four Brain Surgeries, Total Deafness, and Refusing to Break | McKinnon Galloway

Four Brain Surgeries, Total Deafness, and Refusing to Break | McKinnon Galloway

McKinnon Galloway was diagnosed with NF2 at 16 after a routine MRI for a volleyball concussion revealed two brain tumors. What followed was years of chemotherapy, a phase-one clinical trial, four brai...

7 Elo 1h 31min

A School Shooting, a Shipwreck, and the Long Run to Sobriety | Mishka Shubaly

A School Shooting, a Shipwreck, and the Long Run to Sobriety | Mishka Shubaly

Mishka Shubaly has lived several lives: gifted student, touring musician, Columbia-trained writer, addict, shipwreck survivor, ultrarunner, Yale professor, and the editor who helped Ken Rideout turn h...

5 Elo 2h 8min

One Life, Two Hearts: Surviving Cancer, Loss and Heart Failure | Dr. Dawn Mussallem

One Life, Two Hearts: Surviving Cancer, Loss and Heart Failure | Dr. Dawn Mussallem

Dr. Dawn Mussallem was a young medical student when she collapsed and doctors discovered a 15-centimeter tumor wrapped around her heart. She was diagnosed with stage IV diffuse large B-cell lymphoma a...

31 Heinä 1h 34min

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