2026 Update: Tony

2026 Update: Tony

Author: Pushkin Industries March 12, 2026 Duration: 42:51

Today, we speak with Jonathan's longtime friend Tony. A lot's changed in his life since the episode came out ten years ago. 

Tony messed up his relationship with each of his three godchildren owing to three difficult chapters in his life. Now, childless and single in his late 40’s, and fearing he may never have kids of his own, Tony wants to win them back.

You can sign up for our free newsletter at patreon.com/heavyweight

This episode was produced by Jonathan Goldstein, Wendy Dorr, Chris Neary, and Kalila Holt, with editing by Jorge Just and Alex Blumberg. Special thanks to Emily Condon, Anna Asimakopulos, and Jackie Cohen. The show was mixed by Haley Shaw. Music by Christine Fellows, John K Samson, Blue Dot Sessions, Michael Smith, Wonderly, and Hew Time. Our theme song is by The Weakerthans courtesy of Epitaph Records. Mixing on this update by Sarah Bruguiere.

See omnystudio.com/listener for privacy information.


There’s a particular kind of memory that doesn’t fade-it’s the unresolved moment, the regret that quietly shapes a life. Heavyweight, from Pushkin Industries, is built on the belief that it’s never too late to go back and try to set things right. Host Jonathan Goldstein doesn’t just reminisce; he gets in the car, makes the phone call, and arranges the meeting. Each episode is a deeply human, often surprisingly funny journey into someone’s past to confront a lingering question: an apology never given, a friendship lost over a misunderstanding, a childhood promise broken. The tone here is a unique blend, fitting its categories of Society, Comedy, and Culture-it’s empathetic and thoughtful, yet laced with Goldstein’s wry, self-deprecating humor. You’ll hear the awkward silences, the nervous laughter, and the genuine breakthroughs. This isn’t a podcast about easy answers; it’s about the messy, courageous, and cathartic process of seeking closure, one personal heavyweight at a time. The conversations are intimate, the stories are specific, and the emotional weight is real, making for listening that is both moving and unexpectedly uplifting.
Author: Language: English Episodes: 122

Heavyweight
Podcast Episodes
#19 Joey [not-audio_url] [/not-audio_url]

Duration: 41:39
Joey recently had a very bad day, all due to awkward misunderstandings. So now, he's enlisted the help of Jonathan "Debonair" Goldstein and Jonathan’s friend Gregor to redo the day and set things right.
Zoe, PJ, and Chanel [not-audio_url] [/not-audio_url]

Duration: 39:27
Heavyweight performed a sold-out live show in Brooklyn, NY, last June. Jonathan is joined by This American Life’s Zoe Chace and Reply All’s PJ Vogt to talk about Heavyweight stories that never made it onto the air… until…
#18 Sven [not-audio_url] [/not-audio_url]

Duration: 32:50
Sven was on a jury that sentenced a man named Paul Storey to death. He's regretted it ever since. Then, eight years later, Sven gets an email from Paul’s mother.
#17 Skye [not-audio_url] [/not-audio_url]

Duration: 43:09
When Skye was 11, her best friends turned on her out of seemingly nowhere. Now Skye has a son who's 11, & he can’t believe his mom never asked her friends why they did it. So, 30 years later, Skye & her son set off to fi…
#16 Rob [not-audio_url] [/not-audio_url]

Duration: 53:02
Rob remembers breaking his arm as a kid. But the rest of his family says it never happened. Did he break his arm? The answer will determine Rob’s sanity.
#15 Dina [not-audio_url] [/not-audio_url]

Duration: 35:05
During a visit back home, Jonathan’s mother inadvertently admits something that forces him to question his past. In this season finale, Jonathan turns the mic around on himself for one of the more personal episodes of th…
#14 Isabel [not-audio_url] [/not-audio_url]

Duration: 36:54
In 1999, an old suitcase was found abandoned on a Brooklyn street corner. The suitcase contained 5 years worth of love letters between a young man and young woman. In this episode, Jonathan tries to track them down.
#13 Kenny [not-audio_url] [/not-audio_url]

Duration: 46:04
Ken Carter was a Canadian daredevil who dreamt of performing the biggest stunt the world had ever seen. For 5 years he prepared, only to have his dream hijacked at the very last moment by the very last person he ever exp…
#12 Jesse [not-audio_url] [/not-audio_url]

Duration: 36:12
Four years ago, Jesse was hit by a car and nearly died. Now he wants to find the driver. And thank him.
#11 Christina [not-audio_url] [/not-audio_url]

Duration: 40:24
When Christina was in 11th grade, her foster mother made her quit playing basketball. After that, she felt like her life never got back on course. And so, she’s always wanted to ask her foster mother: why’d you make me q…