The Tony Kornheiser Show

Episode: "Was it freeing?"

Date: December 23, 2025
Host: Tony Kornheiser
Guests: Michael Wilbon, Chuck Todd, Chuck Culpepper

Episode Overview

This episode of "The Tony Kornheiser Show" blends Tony’s characteristic blend of sports talk, life anecdotes, and playful banter among his network of friends. The conversation covers NFL news and controversies, stadium relocations, playoff scenarios, a humorous look at sports betting, and a deeply engaged discussion with guest Chuck Culpepper about the College Football Playoff system. The episode is suffused with Tony’s wry observations, memory-lane strolls, and the distinct rhythm and camaraderie loyal listeners expect.

Main Discussion Segments

1. Life Updates, Tech Grievances, and Emails from the Past

[01:12 - 06:01]

• Tony opens with a classic rant: his phone is failing to deliver emails, causing daily anxiety and a sense of lost connection.
  • "There are thousands of emails stacked up and flying around the atmosphere somewhere. Average daily intake, 250 at least." – Tony ([02:29])
  • He jokes about missing bills and being blamed for technological errors beyond his control.
• Michael echoes the frustration with "inbox zero" and the anxiety of digital life.
• Tony shares a warm anecdote about receiving an email from an old camp friend, Alan Legotte, after 70 years, highlighting the pleasant surprises of aging and longevity.
  • "He's the oldest man still working. Because I'm the oldest man still working." – Tony ([05:38])

2. NFL Roundup: Game Recaps, Surprises, and High Stakes

[06:01 - 13:02]

• Recap of Monday Night Football: Brock Purdy throws five TDs for San Francisco in a decisive win over Indianapolis.
  • "San Francisco handily defeated Indianapolis." – Tony ([06:02])
  • Discussion about the strength of the NFC West: 49ers, Seahawks, and Rams all strong playoff contenders.
• Dissection of DK Metcalf's two-game suspension for taking a swing at a fan in the stands:
  • "You can't take a swing at a guy in the stands. Doesn't matter what he says, you walk away." – Tony ([07:20])
• Cheerful complaints about being bumped from ESPN by the Idaho Potato Bowl running over, poking fun at TV scheduling chaos.

3. Stadium Relocations: Kansas City Chiefs and "Regional Identity"

[08:00 - 13:02]

• Tony expresses disbelief and dismay at news that the Kansas City Chiefs may leave Arrowhead Stadium (Missouri) for Kansas.
  • "To me, I don’t understand this...to leave Missouri, to go to Kansas?" – Tony ([09:09])
  • Recalls the pain of the Jets and Giants leaving New York for New Jersey, emphasizing the gravity of sports and city identity.
• Guests discuss the complex identity and rivalry between Kansas City, Missouri and Kansas City, Kansas.
  • "The regional identity of Kansas City, Missouri versus Kansas City, Kansas. If there is any animosity..." – Michael ([10:56])
• The contrasting fates of city names, capitals, and a humorous suggestion to rename cities for clarity.

4. Weekly NFL Picks with Chuck Todd & Reginald the Monkey

[14:46 - 30:15]

Banter and Betting Records

• Chuck Todd celebrates a week over .500: "He's 58, 57, and 1." – Tony ([14:47])
• Ongoing inside joke and debate: the "over/under" direction of toilet paper rolls.

Game Picks Breakdown

• Picks include analysis and skepticism about playoff scenarios, team motivations, injuries, and playoff odds.
  • Dallas-Washington: "You look at the Christmas Day lineup. Netflix wants a refund." – Wilbon ([17:45])
  • Texans-Chargers: "I love this Texans defense...I think if anybody gets to the Super Bowl, that isn't Josh Allen in the AFC, I think it's these guys." – Wilbon ([19:04])
  • Jacksonville's resurgence and Trevor Lawrence's growth: "In the last four games, Trevor Lawrence has accounted for 14 touchdowns, running and passing, no interceptions. So he's closing like he is." – Tony ([21:17])
  • Philadelphia-Buffalo: both teams lack urgency, "Looks good on paper but..." – Wilbon ([23:45])

The Monkey’s (Reginald’s) Picks

• Reginald the Monkey, a running comedic bit, selects his "bets" based on whimsical stories—like attending charity balls in Monaco or showing photos with celebrities.
  • "It’s a lost season." – Tony, on the Monkey's betting record ([28:02])
  • Chuck Todd spins yarns about zoo adventures, random encounters (Snooki, Helen Hunt), and dancing to the Vogues, all in service of Football picks.

5. College Football Playoff and Guest Interview: Chuck Culpepper

[31:01 - 44:17]

Road Wins and Coaching Carousel

• Discussion of Alabama and Miami winning tough road playoff games.
  • "It interrupted that little mini trend of the first year." – Chuck Culpepper ([31:37])
• Kaylin DeBoer’s coaching brilliance, future at Alabama, and rumors about Michigan's vacant position.
  • "I would be stunned if that happened...would it be a good pick for Michigan? I think yes. But would he do it? That's shocking to me." – Chuck ([34:27])

Notre Dame’s Missed Opportunity

• Tony and Chuck lament that Notre Dame could’ve beaten both Miami and Texas A&M based on recent play.

Playoff Structure: Power vs. Group of Five

• Tony argues against including Group of Five teams like Tulane and James Madison, preferring a purely meritocratic 12-team playoff.
  • "I don't think it's a charity tournament. I would have put Texas and Notre Dame over Tulane and James Madison." – Tony ([38:29])
• Chuck responds that variety and access are part of what makes American sports playoffs magical:
  • "I just like the idea of the variety. Picking the best 12 teams is always going to be impossible." – Chuck ([38:34])
  • Compares football to basketball, noting why upsets are less feasible in football.

Who’s Vulnerable?

• Discussion of the top four playoff seeds, with speculation that Texas Tech may be most at risk.
  • "Even though Ohio State lost to Indiana, I still don’t see many vulnerabilities there." – Chuck ([41:31])
• The effect of lay-offs before playoff games and how it might disadvantage higher-seeded, idle teams.

Preview and Assignment

• Chuck will cover the Alabama-Indiana semi-final as his marquee assignment.

Best Quotes & Moments

• On aging and memory:
  • "I can remember song lyrics. And I can remember to be nervous that my dog probably has to go out right now." – Tony ([13:04])
• On technological anxiety:
  • "I want to slam the phone down and break it into a thousand pieces, but I still need it as a phone." – Tony ([03:51])
• On Bowl Game Overload:
  • "There are so many bowl games that are nonsensical." – Tony ([16:56])
• On KC Chiefs Moving to Kansas:
  • "To me, you know, it’s unthinkable. I’m not saying it’s bad. Like, I lived with this when the Jets and Giants left New York to go to New Jersey, and it’s over 50 years and still stinks." – Tony ([10:08])
• On NFL Parity:
  • "It’s the best season the NFL has had in years. It is." – Tony ([26:16])
• Humorous take on betting monkey:
  • "It’s a lost season, you know." – Tony ([28:02])

Notable Timestamps

• 00:00 – 01:12: Tony’s comedic cold open and add spot (skip for main content).
• 01:12 – 06:01: Rant on tech, memories of old friends, and generational connection.
• 06:01 – 13:02: NFL week recap, league standings, Arrowhead stadium controversy.
• 14:46 – 30:15: Chuck Todd’s NFL picks, how to handle toilet paper, and Reginald the Monkey’s comic predictions.
• 31:01 – 44:17: Chuck Culpepper on college football playoffs, playoff expansion philosophy, and game previews.

Conclusion

"Was it freeing?" is a classic installment of The Tony Kornheiser Show: lively, unscripted, and unfiltered. Tony, Michael, Chuck Todd, and Chuck Culpepper mix deep sports analysis with irreverence, humor, and reflections on nostalgia and aging. The episode is a great snapshot of current NFL and college football topics – particularly the debate over playoff composition – but it’s equally about the joys (and pains) of everyday life in the Kornheiser universe.

For more music by Alexa and the Old Fashions (as featured in this episode), check out the closing tracks.