Dan Bernstein Unfiltered – "Remembering Terry Boers"

Episode Date: January 26, 2026
Host: Dan Bernstein
Guest/Co-Host: Matt Spiegel

Overview

In this deeply personal and evocative episode, Dan Bernstein and Matt Spiegel reminisce and pay tribute to the late Chicago sports radio legend Terry Boers. The conversation unfolds as both a heartfelt mourning and a celebration of Terry's life, his candid humor, his complex yet approachable nature, and his enduring impact on Chicago sports media. Listeners are treated to poignant stories, laughter through grief, and reflections on friendship, mentorship, and the unique Chicago radio experience.

Key Discussion Points and Insights

Processing the Loss of Terry Boers

• Initial Reaction:
  Dan shares the surreal mix of shock and sadness learning about Terry’s passing, despite knowing he’d been in failing health.
  • “I knew that he was in failing health. I didn't know that there was something that emergent, that pressing, that urgent. And then it just kind of hit like a ton of bricks.” (Dan, 00:08)
• Grieving with the Community:
  Dan and Matt express gratitude for the overwhelming outreach from listeners and fans. Dan is curating memories and emails to present at a future event honoring Terry.
  • “Everything that you've been sending in I'm keeping... and I want to be able to present you as a listener. I want you to have a voice.” (Dan, 00:44)

The Complexity and Joy of Mourning Terry

• Laughing Through Grief:
  Both hosts note the difficulty staying sad because memories of Terry inevitably bring laughter.
  • “You can't think about Terry Boers without laughing or smiling about something. It's impossible. And what a legacy that is.” (Dan, 03:20)
• No Right Way to Grieve:
  Dan reflects on advice from his father, reinforcing that mourning is personal and that “we all have our moments.”
  • “There's no playbook. There's no right way... and every time I think of Terry, I'm laughing about something.” (Dan, 05:25)

Terry’s Legacy in Sports Radio and Beyond

• Honesty, Humor, and Silliness:
  • “Terry being Terry was his magic... just what made him so special and such a sui generis individual. There will never be another quite like that.” (Dan, 01:30)
  • “I was really glad that our first guest on the new 312Sports Podcast Network was Terry. You know, it just seemed like the right thing to do.” (Matt, 10:41)
• Mentor and Friend:
  Both hosts recall Terry’s egoless leadership. He treated everyone—from interns to co-hosts—as equals, fostering an open, collaborative environment on and off air.
  • “He made me feel as a day one executive producer of a show, he made me feel this way as an intern, that I was part of the show, that I wasn't working for Terry. I Wasn't working for Boars and Bernstein.” (Matt, 21:24)
  • “There was never a hierarchy. There's never a pecking order.” (Dan, 23:56)

Classic Memories and Behind-the-Scenes

• Radio Innovations:
  The duo recounts how their show transformed Chicago radio by making everyone—host, producers, board ops—a regular on air, breaking the ‘wall’ between host and staff.
• Insider Stories & Favorite Bits:
  • “When we were in Glendale... the lookout ducks, the Charlie Steiner interview, the lookout ducks... he whispers 'by cracky'... Jason Goff just falls to the ground.” (Dan, 12:38)
  • “Terry had a gift... he could talk to someone face to face, obliterate them... and they walked away with a smile and a laugh and had the best time of their life.” (Matt, 42:03)

Terry’s Characteristics and Values

• Egoless, Yet a Quiet Giant:
  • “He was egoless... a superstar in what we did... yet the greatest self doubter I’ve ever known.” (Matt, 25:44)
  • “He didn't care how he appeared or looked... if you laughed and felt better after that interaction, then Terry, his goal was met.” (Matt, 43:00)
• Strong Moral Compass:
  Terry advocated for fairness, stood up for what was right, and wouldn't hesitate to rebuke injustice or mistreatment.
  • “All of that joy and all of his rock solid moral compass... He never wavered in that stuff. If ever it’s like, oof. I don’t know what to do, because. Yeah, you do. I don’t know what to. Yeah, you do. You know what's right, you know what's wrong.” (Dan, 56:04)
  • [Matt’s story of Terry defending a woman at a restaurant: 60:30–62:07]

Personal Impacts and Contemplating Mortality

• Friendship’s Importance and Transience:
  The passing of Terry prompts Matt and Dan to reflect on time, family, and being present.
  • “He always was where his feet were.” (Matt, 29:16)
• Father Figure and Mentor:
  • “He became a father figure... his disappointment was never umbrella in judgment or anger. It was always umbrella in love.” (Matt, 26:57)
  • “For me, it was a combination, like in, within the industry, I'd say it was... much older brother and goofy uncle.” (Dan, 53:08)

The Tavern Tours and Meeting Listeners

• Connecting with Fans:
  Dan describes their “Who Needs Two Tavern Tour” and how it brought them into hundreds of local bars, putting them face-to-face with listeners across Chicagoland.
  • “We added this up at some point: it was 10 years... over 500 Boars and Bernstein shows were done throughout the Chicagoland area.” (Dan, 31:53)
• Memorable Fan Encounters:
  • “It helped you get to know Terry... Cause he's there. He is. It's Terry and he's sitting in your bar.” (Dan, 32:44)

Writer and Journalist’s Integrity

• Background and Approach:
  Dan details Terry’s serious journalistic training, his deadline writing skill, and his belief in real reporting as a foundation for sports commentary.
  • “Read Terry's book, it's really important to understand his background in journalism... so much of his essence was journalistic and about finding things out and telling you things about the teams that the teams didn’t want you to know.” (Dan, 37:28)

Stories from the Road

• Traveling as Family:
  Tales of Arizona, spring training, late night beers, and Terry’s talent for making strangers instant friends and targets for his jokes.
  • “I was good at always encouraging Terry to interact with strangers just for our own benefit, you know.” (Matt, 50:08)

Legacy and Lasting Influence

• Inside Jokes and Lasting Phrases:
  From odd sound effects to recurring bits (“TB Diddlers,” “High Noon”), much of the duo’s lingo and humor remains in Chicago sports radio.
  • “If you have people saying things the way you said them just because it’s fun to do... If that’s part of your legacy, you're doing something right.” (Dan, 73:05)
• Production Pieces:
  “One of Tani's production pieces with all of Terry's noises... that's the funniest stuff.” (Matt, 73:15)

Terry's Reflections in His Own Words

• [Terry Boers, 78:32]:
  "Working with Dan for as long as I did, I know you figured it must have made me crazier. I, you know, I thought that we meshed pretty damn well together, which is very difficult to do. And we did, and he's terrific... All of that stuff I don't miss now, isn't that weird?... I fought as, as hard as I can fight, and I'm going to keep fighting as hard as I can. But them, no, I miss it all. I miss it all. I miss the people. I miss the whole thing."

Notable Quotes & Memorable Moments

• On Mourning Terry:
  • "Every time I try to be sad, I can't. Because you can't think about Terry Boers without laughing or smiling about something." (Dan, 03:20)
• On Terry’s Humor:
  • “He could talk to someone face to face, obliterate them, eviscerate them, insult them, and they walked away with a smile and a laugh and had the best time of their life.” (Matt, 42:03)
• On Being Present:
  • “You gotta be where your feet are. And that's what I loved about Terry. Terry always was where his feet were.” (Matt, 29:16)
• On Equality and Collaboration:
  • “There was never a hierarchy. There's never a pecking order.” (Dan, 23:56)
  • “He made me feel ... that I was part of the show, that I wasn't working for Boars and Bernstein. I wasn't working for Terry.” (Matt, 21:24)
• On Journalistic Integrity:
  • “So much of his essence was journalistic and about finding things out and telling you things about the teams that the teams didn't want you to know.” (Dan, 37:28)
• Self-Doubt & Humor:
  • “A superstar ... yet the greatest self-doubter I've ever known.” (Matt, 25:44)
  • "It made him uncomfortable that it mattered." (Matt, 26:10)

Favorite Listener Story

• “I ran into Terry and he called me a stupid fat bastard and it was the best moment of my life, and I laughed my ass off and I'll never forget it.” (Dan quoting listener email, 42:27)

Timestamps for Key Segments

• Dan processes the news, thanks fans: 00:08–05:30
• Laughing through tears & personal grief wisdom: 05:30–07:30
• Terry’s radio presence, enduring humor: 07:56–13:00
• Radio show origins, egoless leadership: 21:12–24:54
• Behind-the-scenes camaraderie & road trip stories: 47:06–55:12
• Terry’s moral compass and standing up for what’s right: 56:04–62:07
• Terry's challenges with technology (TV remote stories): 62:38–63:40
• Terry’s lasting impact—production bits, inside jokes: 70:15–74:11
• Terry Boers, interviewed, reflects: 78:32–80:40

In Terry's Style: How to Remember Him

• Pour out a Jack and Diet.
• Watch some harness racing (YouTube if you can't find it live).
• Tell the truth, make people laugh.
• Be present—be where your feet are.
• Laugh at yourself, include everybody, and show up as your full honest self.

Closing Thoughts

This episode is less a eulogy and more a true Chicago Irish wake: full of love, stories, and laughter. The hosts’ voices tremble at times, but through every memory and offbeat anecdote, Terry’s unique blend of candor, wit, heart, and decency shines. To long-time listeners and new fans alike, Terry Boers is warmly, honestly, and hilariously immortalized.

For dedicated fans and newcomers, this episode is an essential listen—not just as a tribute to one man, but as a celebration of what makes Chicago sports media, friendship, and authentic radio so meaningful.