The Herd with Colin Cowherd

"3 & Out" with John Middlekauff – August 25, 2025

Main Themes:

• Eagles GM Howie Roseman's roster management and Philadelphia's "GM-first" model
• The challenge facing rookie quarterback Caleb Williams and the evolution of NFL quarterbacking
• Tommy Fleetwood’s popular first PGA Tour win and reflections on golf, LIV/PGA divide, and the Ryder Cup
• NFL training camp/preseason observations and the ups/downs of roster cutdowns

1. Overview

In this edition of "3 & Out," John Middlekauff, recording from Hawaii, dives deeply into the major NFL storylines of late August: Howie Roseman's unique team-building approach with the Philadelphia Eagles, pressure and developmental arcs for young QBs like Caleb Williams, and observations on preseason dynamics. He closes with extensive PGA Tour talk, lauding Tommy Fleetwood’s emotional and long-awaited first win, before fielding listener golf questions and discussing LIV, the Ryder Cup, and more.

2. Key Discussion Points & Insights

Howie Roseman and the GM-First Eagles

[03:57-13:00]

• Howie’s Aggressive Offseason Moves: Roseman has set a record with multiple trades this August, possibly up to five or six this preseason, showcasing a willingness to tweak roster depth relentlessly.
• The GM vs. Coach Dynamic:
  • “The difference in Howie than the majority of these organizations is how he is able to take a big picture view of his roster. Why? Because he’s not a coach.”
  • Coaches often get too emotionally attached to players they're directly working with. GMs like Roseman are able to separate ego and sentiment for minor roles, swapping backups and special teamers as needed for the greater good.
  • “This is the time to operate like baseball, where there’s no emotion—they’re all just widgets on a sheet.”
• Contrast with Other Teams:
  • The Cowboys (Jerry Jones) blend roles; Jerry’s emotional approach contrasts with Howie’s analytical detachment.
  • “...when you watch them play over the last several years, when it works, it looks as good as any.”
• Philly’s Super Bowl Window: Eagles’ emotional GM separation and structural clarity is a huge edge; barring injuries, Middlekauff considers them NFC favorites.

Notable Quote

• “One of their greatest strengths... having the GM run the roster... is the emotional separation from the players.” — John Middlekauff [12:20]

The Reality for Young Quarterbacks: Caleb Williams, Shador Sanders, and NFL Evolution

[13:01–28:30]

• Caleb Williams’ Rookie Challenge:
  • Bears coach Ben Johnson’s recent critical comments about “offensive execution... a complete embarrassment,” highlight the league’s modern impatience.
  • Middlekauff: “You’re going into year three to prove you can play or they will get rid of you.” [19:40]
  • Caleb won’t receive a multi-year leash if he doesn’t adapt quickly (e.g. Trey Lance).
• Evolution of Quarterback Evaluation:
  • Past: Under-center, run-first offenses, limited passing attempts.
  • Now: QBs like Mahomes come from spread systems; evaluation is actually easier, but the lessons remain old-school—get rid of the football fast and on time.
  • Andy Reid anecdote: “I just siphoned the passes he threw behind the line of scrimmage... still 40 passes I got to evaluate. Never thought of it that way.” [16:40]
• Key QB Development Insight:
  • “What will never change... you have to get rid of the football.” [17:44]
  • Playmaking outside the pocket helped Russell Wilson, and (briefly) Deshaun Watson, but holding the ball too long is a coach-killer.
• Caleb/Ben Johnson Dynamic:
  • Ben Johnson, new Bears head coach, is a hard-nosed offensive mind who will not tolerate “hold the ball” heroics.
  • “If it’s not going well... he’s not getting all year to start. If it’s going shitty, if it’s going well—yeah, 100% [he keeps playing].” [26:56]
  • Chicago’s investment in the backup QB shows leadership wants a live backup plan if Caleb struggles.

Notable Quotes

• “When you watch Patrick Mahomes in that game... what he’s great at and what makes him an all time great is on third and six... that ball will be out of his hands.” — John Middlekauff [23:45]
• “There’s no disputing [Caleb Williams'] arm talent... but in the construct of an NFL offense... holding onto the football 100% will not be tolerated there.” — John Middlekauff [25:10]

Preseason & Roster Cutdown Observations

[28:31–36:45]

• Preseason Erosion:
  • Once a valuable tool escalating week after week, now preseason is “an awful product.” Coaches barely play starters, turning games into unwatchable battles between backups, but they’re still TV ratings winners.
  • Suggestion: Televised joint practices may eventually be more compelling.
• Roster Cuts and Their Silver Lining:
  • Middlekauff reflects on delivering the “you’ve been cut” news to players; it’s gut-wrenching but for many, just the start.
  • Practice squad stigma is fading; over half those cut are elevated during the year, with many becoming key starters over time.

Notable Quote

• “Sometimes these moments are the best thing that ever happened to you... If you go in with the mentality that like, I got time on my side... opportunities are guaranteed to arise.” — John Middlekauff [33:00]

Tommy Fleetwood’s Emotional PGA Tour Win & Golf Reflections

[36:46–54:25]

• Fleetwood’s Breakthrough Moment:
  • Tommy Fleetwood, long one of the most beloved winless players, captures his first PGA Tour victory.
  • “His willingness to speak after these moments... that resonates with people. You’re like, ‘God, what a good... that sucks, you feel for him.’” [38:50]
• Why Fans Love Fleetwood:
  • Vulnerability after losses draws fan empathy; contrast with Colin Morikawa’s standoffishness (“I don’t owe you guys anything…”).
  • Example: “There was a reason today that in Atlanta, Georgia, they started chanting for a guy from the UK—‘Tommy, Tommy!’” [42:10]
  • “A winner is just a loser that kept on trying.” [45:05]
• Pro’s Relatability Matters:
  • Fleetwood’s narrative—perennial close calls, emotional interviews—made his win a moment even casuals celebrated.
  • “If you’re going to win your first tournament in the States, pretty cool it happens for $10 million.” [46:55]
• LIV & Ryder Cup Thoughts:
  • LIV’s future hinges on big names (Rahm & Bryson) making noise; the sport as “showbiz.”
  • U.S. Ryder Cup team predictions: Keegan Bradley now a lock, Colin Morikawa in jeopardy, chemistry and likability valued almost as much as skill.

Notable Quote

• “...humans can relate to losing, can relate to struggle, whether it’s in a PGA golf tournament or in our everyday lives. Tommy Fleetwood... honestly feels... just seems like a great guy.” — John Middlekauff [46:20]

Rapid-Fire Golf Q&A

[54:25–67:56]

• Patrick Cantlay’s Reputation:
  • “Cantlay is everything that golf was pre-Tiger... douchey country club rich kids. Plays slow as molasses.” [54:40]
• Tiger Woods’ Skills:
  • Middlekauff on Tiger’s viral driving feats: “He’s the king... spent most of his life with a golf club in his hands.”
• Golf Equipment Advice:
  • Stiffer shaft = better if you swing hard/from an athletic background.
• Liv’s Future:
  • New signings may not move the needle; true unification is the only real growth strategy.
• Golf Dress Codes:
  • Predicts shorts soon to be allowed in pro play: “If these players go to Roll Up and say we don’t want to wear pants anymore, it’s a done deal.” [65:50]

Notable Quotes

• On Cantlay: “He for as enjoyable and as cool as it was watching in the Ryder Cup... in a PGA Tour event, it can be hard.” [55:05]
• On golf’s business future: “...if I wouldn’t have gone to the [LIV] event, I couldn’t speak to it. You go to the event, it is cool... but no one is watching on TV.” [59:20]

3. Memorable Quotes (with Timestamps)

• “This is the time to operate like baseball, where there’s no emotion. They’re all just widgets on a sheet.” — John Middlekauff [09:58]
• “You get three years in this modern NFL to prove you can play, or they will get rid of you.” — John Middlekauff [19:43]
• “There’s no disputing [Caleb Williams’] arm talent, but holding onto the football 100% will not be tolerated there.” — John Middlekauff [25:10]
• “The preseason... is just unwatchable. It truly is.” — John Middlekauff [31:44]
• “A winner is just a loser who kept on trying.” — John Middlekauff, on Tommy Fleetwood [45:05]
• “Cantlay is everything that golf was pre-Tiger... douchey country club rich kids. Plays slow as molasses.” — John Middlekauff [54:40]

4. Timestamps for Important Segments

• 03:57 – 13:00: Howie Roseman and Philly’s GM-Centric Model
• 13:01 – 28:30: Quarterback Evolution and Caleb Williams’ Short Leash
• 28:31 – 36:45: Preseason Insignificance & Practice Squad Perspective
• 36:46 – 54:25: Tommy Fleetwood’s Breakthrough Win and Golf Fan Psychology
• 54:25 – 67:56: Rapid-Fire Listener Golf Q&A: Cantlay, Tiger, LIV, Dress Codes

5. Takeaways for New Listeners

• The Eagles’ structure—putting true roster power with the GM—creates unparalleled flexibility and long-term success.
• NFL QBs must adapt immediately; patience for slow development is a thing of the past (Caleb Williams under intense scrutiny).
• Fans relate to honest, vulnerable athletes—Tommy Fleetwood’s journey is a case study in public sports empathy.
• Golf is as much about narrative and relatability as skill; media savvy matters.
• The NFL preseason is broken, the practice squad system is not a death sentence, and golf (like the NFL) will continue adapting to the next generation’s cultural expectations.