When something big happens in Chicago sports, who do you turn to?

Tom sits down with Chicago Sun Times media columnist Jeff Agrest to talk about the state of Chicago sports radio — from Dan Bernstein’s impact to whether today’s shows have lost some of the edge and tension that once defined them.

They dig into media power, trust, conflict, the rise of podcasts, and how Chicago’s sports ecosystem is changing.

It’s about how sports media shapes the way the city reacts.

Bobbleheads. Throwbacks. Cade Horton truck-stop couture.

The Cubs’ 2026 giveaway calendar might be one of their best — but what does it actually say about the brand?

Tom and Andy Dolan from the Pointless Exercise Podcast break it down, plus a quick detour into Chicago sports media power rankings.

In this episode of Lore, Brett Taylor looks back on the unlikely arc of Bleacher Nation — from a side project in the early blog era to a daily stop for Cubs fans during the rebuild, the rise, and the championship.

The timing, fandom, and why community mattered more than access. Brett reflects on what Cubs fans needed during the lean years, what traditional media couldn’t always provide, and how Bleacher Nation found its voice by staying close to the reader.

It’s a conversation about luck, trust, and why the things that work eventually have to adapt — without losing what made them matter in the first place.

Luke Stuckmeyer of CHGO unpacks the origins and lasting impact of Beer Money, one of Chicago sports TV’s most beloved trivia segments. From its early inspiration to the moments fans still talk about years later, Luke walks through how the show found its voice — and its audience.

The conversation also dives into behind-the-scenes production, why embracing the absurd made the show work, and what Beer Money taught Luke about live TV, sports fandom, and Chicago’s unique media culture.

Chicago sports radio voice and musician Matt Spiegel joins The Lore to talk about the moments and sounds that shaped how Chicago sports felt — from baseball broadcasts and iconic theme music to the Bulls’ dynasty and the songs that defined entire eras.

Spiegel reflects on how music and sports culture fused in the ’70s, ’80s, and ’90s, why certain songs became inseparable from Chicago teams, and what it was like being behind the scenes at The Score during some of the city’s most defining moments.

It’s a conversation about memory, identity, and why the soundtrack of Chicago sports still hits just as hard as the highlights.

Tom is joined by Matt Trueblood of Northside Baseball and Baseball Prospectus.

Matt gives us his first impressions of Cade Horton.

They break down the challenge of adding a front-line starter. Wonder if adding a "guy" in the pen for Craig Counsell to trust is the move. Discuss Ben Brown's best role.

Cubs On Deck's Greg Huss discusses the current state of the Chicago Cubs prospects.

Cade Horton, Matt Shaw, and Moises Ballesteros are the focus.

They delve into the dynamics of the Cubs' defense, the impact of PCA on the team's performance, and the potential asks from other teams in trades.

ESPN college hoops broadcaster, formerly of WGN and WSCR 670 Jordan Bernfield talks Chicago Cubs' surprising start to the season and sustainability.

The impact of Kyle Tucker on the ownership decisions for Tom Ricketts.

David Kaplan's report on Cubs willingness to sign Tucker.

They explore the dynamics of mega contracts in the current market and Jed Hoyer's performance.

The Athletic's Jon Greenberg discusses the landscape of Chicago sports management.

The impact of Ben Johnson on Ryan Poles and the draft.

How Jed Hoyer has put the onus on Tom Ricketts. The comparison of game experiences between the Cubs and White Sox.

They also touch on the implications of Dan Bernstein's departure from the Score.

CHGO's Cody Delmendo talks Chicago Cubs.

Pete Crow Armstrong (PCA) fun ride and realistic expectations for this year?

How do the Cubs replace Justin Steele?

Who is currently in Cody's circle of trust in the bullpen?

Why Rick Sutcliffe is an occasional needed jolt to the booth.