The Herd with Colin Cowherd – "3 & Out: Massive Mailbag"

Host: John Middlekauff
Date: February 24, 2026

Brief Overview

This special "massive mailbag" episode, hosted by John Middlekauff, focuses on wide-ranging listener questions about NFL roster-building philosophies, contract trends, team strategies for the offseason, stadium debates, NIL money in college sports, personal anecdotes, and reflections on sports culture. The tone is candid, energetic, and conversational, touching on both hard football analysis and light-hearted dad and life content.

Key Discussion Points & Insights

1. Quarterback Contracts and Roster-Building Trends

• Contract Strategy Shift:

  • John discusses how teams are rethinking paying "max" contracts to quarterbacks who aren't truly elite, drawing parallels to the NBA's flawed max-contract system:

    "The NFL turned into the NBA where it's like, not everyone's a max. Guy Curry and LeBron are on a max, and so is Zach Levine. They're not the same." (04:45)

  • Emphasizes that only true difference-makers deserve top dollar; paying big for fringe QBs hampers roster construction.
  • Highlights examples where elite QBs justify large deals (Mahomes, Allen), but notes mid-tier QBs (e.g., Tua, Kyler) can "derail your franchise" when overpaid.

• Financial Implications:

  • Teams may become more cautious with extensions, especially for players like C.J. Stroud:

    "Even if next year [Stroud] is solid, you win a playoff game, again, like, I'm not giving you 250 million dollars ... There has to be levels." (06:20-07:45)

  • Stresses it's a cap league, not like MLB's unlimited spending.

2. Patriots Offseason & Team-Building Priorities

• Aggressiveness vs. Rebuild:
  • Willing to trade picks for elite talent (Max Crosby), showing more hesitation with older, expensive players (e.g., A.J. Brown).
  • Believes the foundation should be built on offensive and defensive lines:

    "I'm doubling down on the offensive and defensive line. That's all I'm doing ... that's where you win." (09:00)

  • Cites Tennessee Titans' second-round picks (A.J. Brown, Derrick Henry) as transformational.

3. Ken Rideout Interview and Guest Diversity

• Reaction & Future Interviews:

  • Ken Rideout's story resonated deeply—likened to "Whitey Bulger meets Lance Armstrong."

    "When you listen to that, you just can't make that up ... If I had 10 Ken Rideouts, I would interview him over the next month." (11:45)

• Insights:

  • Aims to mix in more unconventional, compelling interviews beyond football figures, especially in the offseason.

4. Bears Stadium & Owner-City Dynamics

• Possible Move to Indiana:
  • John breaks down why the Bears’ potential stadium relocation to Indiana is a real possibility, mainly due to strained relationships with Chicago politicians and financial offers from Indiana:

    "I would say, as I sit here recording this, I would say it is definitely a possibility ... Things are getting weird. There's no way around it." (13:55)

5. Dad Diaries & Parenting Advice

• ROI on Reading and Investing:
  • Discusses investing for his son and the high return of reading early on:

    "The ROI on just, I mean, reading to him right now ... will be higher than any investment you make beside buying an NFL franchise." (15:10)

  • Shares about singing real songs as lullabies and challenges compared to traditional ones, adding a humorous, relatable touch.

6. College Sports, NIL, and Olympic Sports Funding

• Football as Revenue Engine:

  • Explains that football subsidizes non-revenue college sports:

    "The way the golf team or the softball team pays for their flight to wherever is because of the football team. They generate all the revenue and fund and subsidize everything, right?" (17:00)

  • Questions whether separate football-only conferences make sense, laying out why they’re interdependent financially.

• NIL Realities:

  • High school golf phenom Miles Russell turning down $500k shows how big NIL payouts can be—millions from apparel companies are possible:

    "He's making way more money than all the guys that are battling it out on the Korn Ferry Tour ... $500k? Yeah, would get you laughed at by a guy like him." (20:00)

7. Fun Segments and Observations

• Titans' Bald Coaches:

  • Playful shout-out to the Tennessee Titans' coaching staff:

    "Their head coach is bald. Their coordinators, bald ... It is. It's incredible. I mean, what a moment for the bald community." (22:30)

  • Appreciates authenticity in people embracing who they are, whether with weight or personality.

• GLP-1 (weight loss drugs) and Food Talk:

  • Admits being "an eater" and expresses respect for people honest about using weight-loss medication and the struggle with food.

    "You can't outrun a bad diet ... I love to eat, and I love sweets, and it's a battle." (24:10)

  • Jokes about ordering salads with age versus burgers and fries.

8. NFL Coaching Changes and Roster Moves

• On New Coaches (e.g., Mendoza with Raiders):
  • Points out that new hires may struggle when moving from elite programs to franchises with bigger challenges:

    "He played on one of the best teams in the country, one of the best coach teams in the country. That's not the case here." (28:00)

9. Texans & C.J. Stroud’s Future

• Stroud at a Crossroads:
  • 2026 is a make-or-break year for Stroud; extension unlikely unless he elevates further:

    "He has a big year, shows promise, is better in the playoffs ... he'll get a contract ... If he has an up and down season ... just no extension coming." (37:00)

10. Golf in Scottsdale, Arizona

• Course Prices:
  • Golf "is crazy expensive ... nothing cheap here" due to sky-high demand.

    "If you're coming soon, I mean you're talking five, six hundred dollars for golf." (39:05)

  • Suggests considering Phoenix or surrounding areas for less expensive options.

11. Recreation & Travel Advice

• National Parks and Trails:
  • Admits not being a "national park guy" and only personally knows Camelback Mountain, warning of heat danger for non-locals. (41:00)

12. Defensive Strategy and Pickup Sports

• Defense Wins at All Levels:
  • Reader compares rec hockey defense to Seahawks’ approach.
  • John agrees defense differentiates teams at all levels, even in pickup play:

    "If you do do it, big point of difference ... At the highest level you have to play defense." (43:30)

13. Guaranteed Contracts & Load Management Debate

• Realism of Rollbacks:
  • Listener suggests performance-based pay; John explains power of unions makes fully-guaranteed contracts near-impossible to change:

    "Once you've negotiated these guaranteed contracts the way they're ... it rarely comes back the other way." (46:30)

  • Acknowledges incentives may be misaligned, but it's not realistic to reverse.

14. Raiders’ Team Direction & Max Crosby’s Future

• Trade or Build Around?
  • If keeping Crosby, go for it in the short term; if trading, a full rebuild could start.

    "If you go Monday or Tuesday, Max Crosby is available, you will have a bidding war ..." (50:05)

15. Chiefs, McDuffie, and Draft Strategy

• Drafting Priorities:
  • Expects the Chiefs to look at defensive/offensive linemen over RBs or WRs:

    "I'd be stunned if Andy Reid did not take a defensive or offensive lineman. If he stays at 9." (52:55)

  • Unsure of McDuffie trade value but figures a second and a third is plausible.

16. Personal Anecdotes, Listener Shout-Outs, and Addiction Discussion

• Drinking and Parenthood:

  • Parent life has dramatically cut his drinking:

    "All you can think about is, I would rather jump off a bridge than be hungover feeding this baby ... I don't think I've had more than two cocktails in two months." (56:00)

• Addiction & Ken Rideout’s Story:

  • Powerful feedback on Ken Rideout interview—mutual understanding, tackling stigma and struggles:

    "Addiction doesn't run in my family ... But you just let Ken talk and cook, and it's real, because when you hear him speak, like, he ain't bullshitting you." (59:30)

  • Acknowledges listener's recovery; reflects on loss, life, and the universality of struggle.

Notable Quotes & Memorable Moments

• On Quarterback Contracts:

  "If I give Nikola Jokic $60 million a year, he wins the MVP every year. Like, I can't really ask for more. But when I'm giving a guy... $50 million and he doesn't sniff the All Star game, we got a major problem. It's no different at quarterback." (08:10)

• On Ken Rideout:

  "This is like Whitey Bulger meets Lance Armstrong ... you can't make that up." (11:45)

• On the Bears' Stadium Situation:

  "Things are getting weird. There's no way around it." (13:55)

• On NIL Deals:

  "He's making way more money than all the guys that are battling it out on the Korn Ferry Tour ... $500k? Yeah, would get you laughed at by a guy like him." (20:00)

• On the Titans' Coaching Staff:

  "What a moment for the bald community." (22:30)

• On Food and Weight:

  "I love to eat, and I love sweets, and it's a battle." (24:10)

• On Defense in Pickup Sports:

  "At the lowest level you could argue a big point of difference to be good. Like if you wanted to win in high school football ... just be the best defensive team." (43:30)

• On Addiction and Life's Challenges:

  "You just let Ken talk and cook, and it's real ... when you hear it, you know it, and you're listening to the story like, geez, this is intense." (59:30)

Timestamps for Important Segments

• QB Contract Philosophy: 04:45–09:00
• Patriots’ Rebuild Strategy: 09:00–11:20
• Reaction to Ken Rideout Interview: 11:45–13:00, 59:30
• Bears Stadium Debate: 13:55–15:00
• Parenting & Dad Diaries: 15:00–17:00
• College Athletics/NIL: 17:00–21:00
• Titans Coaches Baldness Bit: 22:30–25:00
• Weight, Food, and GLP-1: 24:10–25:00
• Analysis of New Coaches (Raiders example): 28:00–29:30
• C.J. Stroud & Texans Outlook: 37:00–38:30
• Scottsdale Golf Prices: 39:05–40:10
• Recreational Adventures: 41:00–41:50
• Defense in Rec Sports: 43:30–45:10
• Guaranteed Contracts in the NBA: 46:30–47:00
• Raiders & Crosby Trade Discussion: 50:05–51:40
• Chiefs Draft Thoughts & McDuffie Value: 52:55–54:00
• Drinking, Parenthood, and Personal Routine: 56:00–57:30
• Addiction Reflections/Ken Rideout Feedback: 59:30–End

Conclusion

This mailbag episode delivers high-energy, straight-shooting NFL analysis, balanced with humor and authenticity about real-life challenges—from salary cap strategy to personal anecdotes about parenting and addiction. John blends deep football insight with a personable style, making it engaging for both hardcore fans and casual listeners.