The Herd with Colin Cowherd – August 28, 2025

Hour 1: The Cowboys’ Dysfunction, Caleb Williams & Ben Johnson Dynamic, Scott Pioli Interview

Overview

This episode, hosted by Jason McIntyre ("Jay") and Rachel (full names not given), dives into the ongoing chaos surrounding the Dallas Cowboys—including the latest Micah Parsons contract drama—contrasting styles between Chicago Bears head coach Ben Johnson and quarterback Caleb Williams, and features a wide-ranging conversation with former NFL GM Scott Pioli on college football, player contracts, and team building.

Key Discussion Points & Insights

1. Dallas Cowboys’ Culture & the Micah Parsons Situation

Main Theme:
Jay and Rachel break down the ongoing off-field turmoil in Dallas, focusing on the contract standoff with star pass rusher Micah Parsons, and criticize the Cowboys’ “reality TV” approach under Jerry Jones.

Cowboys’ Dysfunction: Why All the Drama?

• The Cowboys are constantly in the media spotlight despite the Eagles being reigning champs and more successful:
  “The media remains obsessed with the wretched Wobegon Dallas Cowboys. Why would that be? Well, wouldn’t you know it, but yesterday Micah Parsons, their star holdout... showed up at an airport... getting a second opinion on his back. He’s not going to be at practice this weekend? Well, that ain’t good.” (Jay, 03:56–05:11)
• Parsons filed a contract grievance; his older brother posts, “It’s going to get ugly. Put your gloves on. This is going 12 rounds.” (05:44)
• Cowboys’ futility: Only NFC team not to reach a conference championship since 2010.
• Jay’s assessment:
  “Jerry Jones is not serious about actual football. The Eagles... are building a juggernaut and Jerry Jones is out here creating reality TV shows. You’ve heard of Love Island. Cowboys, they got Star Island.” (06:56)
• Negotiating history:
  “Every one of these holdouts end in the Cowboys capitulating... Every CD [Lamb], Zeke, Zach—deals get done.” (J. Mack and Jay, 07:54–08:12)
• On the risk to Parsons:
  “Can you imagine the panic Rayshawn Slater would have right now if he were playing for the Cowboys and Jerry was jerking him around? And then he tears his patella tendon in practice and he's out for the year. But, bro, you didn’t get your extension. You just cost yourself a ton of money.” (Jay, 11:09)

2. The Chicago Bears: Caleb Williams and Ben Johnson’s Relationship

Main Theme:
How will new coach Ben Johnson’s structured style mesh with the improvisational flair of QB Caleb Williams? Is the communication coming from Chicago cause for concern?

Contrasting Styles—A Challenge?

• Rachel outlines the key stylistic mismatch:
  “Ben Johnson is a very precise coach... And Caleb Williams has always been more of a freelancer... So for me, the question is how do those two styles merge and can they live together?” (Rachel, 14:58)
• Jay compares vibes:
  “If you compare what’s being said in Chicago, what's being said about Caleb Williams, with the messaging in New York about another rookie quarterback, Jackson Dart—one’s very positive and the other is, Ben Johnson’s... not.” (Jay, 15:41–16:01)
• Ben Johnson’s candid approach:
  “The standard has been set... Is he going to be a finished product here in year two? No... He’s going to take his bumps. But as long as we’re not making the same mistake twice, we’ll be just fine.” (Ben Johnson, as quoted by J. Mack, 24:59)
• Jay worries about the tone:
  “There’s a lot of negativity... a grace period, going to take his bumps. Just a lot of not positive stuff.” (Jay, 25:38)

Will it Work?

• Rachel:
  “It’s hard to tell whether this is just a bumpy start of two styles coming together... once they’ve got it, it’s going to be great. Or if it’s an indication on Caleb Williams.” (Rachel, 26:54)

3. College Football: Arch Manning Debut & Bill Belichick at UNC

• Arch Manning will debut as starting QB for Texas against Ohio State—an unusually tough opener.
  “Are you going to take into account who he’s playing against or just how he does?” (Rachel, 29:44)
• Jay:
  “Even if he’s terrible... this is against Ohio State... But if he goes in there, throws for 300 yards and they win, this hype machine is going to get out of control.” (Jay, 30:15)
• Bill Belichick’s new college coaching gig at UNC draws on lessons he learned from the University of Washington—where he studied how to blend college and pro concepts, and poached assistants and players.
  Rachel: “He didn’t go to Alabama or Ohio State, he went to the smaller program...this is more of what I want to do.” (34:04)

4. Brock Purdy’s Rise: Comparing to Drew Brees

• Vernon Davis compares Purdy to Drew Brees.
  Jay: “Drew Brees? That’s high praise. But I like Purdy—underdog, seventh round pick... just been so good.”
• Rachel: “First 26 games—Purdy has more wins, more accurate, more yards, better TD-to-pick margin, higher passer rating than Joe [Montana] or Steve [Young].” (Rachel, 32:23)

Notable Quotes & Memorable Moments

• On Cowboys’ priorities:
  “Jerry Jones is out here creating reality TV shows.” (Jay, 06:56)
• Micah Parsons’ family’s warning:
  “It’s going to get ugly. Put your gloves on. This is going 12 rounds.” (Micah Parsons’ brother, 05:44)
• On how winning organizations handle extensions:
  “All those guys... got their extensions. Micah Parsons is the only player in this draft to have three all pro seasons.” (Jay, 12:15)
• On Caleb & Ben Johnson:
  “For me, the question... is how do those two styles merge and can they live together?” (Rachel, 14:58)
• On Brock Purdy:
  “I like the cut of his jib... I’m going to be a fan. I’m going to follow him.” (Jay, 31:38)
• On Bill Belichick’s new college approach:
  “He called Washington a ‘template to his program’... the style of their mixing of college and pro convinced him he could do the same thing at North Carolina.” (Rachel, 34:04)

Extended Interview: Scott Pioli, NFL Front Office Veteran (41:30–53:40)

Scott Pioli, former NFL GM, discusses the changing landscape of college football, player contracts (esp. the Parsons saga), and lessons from managing quarterback transitions.

On College Football’s Player Pay Revolution

• Scott consults for NCAA programs:
  “They're trying to figure out their revenue sharing... how they're going to pay student athletes, not only in football, but in every sport.” (Scott Pioli, 42:56)
• He supports athletes being paid, but urges rules that “make some of the crazy a little bit more certain.” (Scott Pioli, 43:13)
• Transfer portal debate:
  “Coaches change jobs, too... We need to put things in that make it more sensible and easier for them to understand why they're doing [it], not just because life's gotten too tough and I'm not starting.” (Scott Pioli, 44:12)

On Dallas/Micah Parsons’ Contract

• “Micah wants to get paid. Micah should get paid... Jerry wants to pay him. They just have to figure this thing out.” (Scott Pioli, 46:12)
• Advice for both sides:
  “Best thing to do is to say nothing publicly... If you talk publicly, someone's going to say something that hurts the other side.” (46:12)
• On the dangers of delay:
  “If you pay someone early, it's going to be at a discount... The earlier that you get a deal done, the more potential savings.” (Scott Pioli, 48:01)
• On why Jerry Jones resists that:
  “He's a billionaire for a reason... He's done something right... why he does it this way, I don't know.” (Scott Pioli, 49:35)

On Brock Purdy’s “Game Manager” Tag

• “A game manager isn't a bad thing... that's part of the job of being the quarterback.” (Scott Pioli, 50:43)

• On quarterback development:
  “There's different kinds of game managers. With Brady [early], he was still developing... he was surrounded by good people and good players. That made his development better.” (51:27)

• On Purdy/Shanahan:
  “Kyle Shanahan is doing with Brock Purdy... quarterbacks need to end up in the right situations and the right marriage.” (Scott Pioli, 52:35)

• “Look at how many games he’s won... did they lose you games? Are they doing dumb things in order for you to lose games? That’s not what you’re looking for, and Brock doesn’t do that.” (Scott Pioli, 53:06)

Timestamps for Important Segments

| Segment | Timestamps | |---------------------------------------------------------------|----------------------------------| | Cowboys & Micah Parsons Drama / NFL Team-Building | 03:17–14:58 | | Bears: Caleb Williams & Ben Johnson Relationship | 14:58–28:53 | | Arch Manning Debut / Belichick at UNC (College Football) | 29:02–36:48 | | Brock Purdy Discourse (Drew Brees, SF QB legacy) | 31:11–33:54 | | Interview: Scott Pioli on College Football & NFL Contracts | 41:30–53:40 |

Summary Table – Main Takeaways

| Topic | Main Takeaway | |-------------------------------|------------------------------------------------------------------| | Cowboys Management | Dysfunction defined by “headline chasing” over football results.| | Micah Parsons Contract | Only elite '21 draft pick w/o extension—team risks losing trust. | | Bears: Williams-Johnson | Unclear fit between QB’s instincts & coach’s structure. | | College Football Changes | NIL & transfer portal drive pro-style athlete management. | | Brock Purdy | Early comparison to legends; “game manager” is smart, not bad. | | Scott Pioli’s View | Paying stars early is best; public drama is bad for both sides. |

Tone & Style of Show

The episode mixes passionate critique (especially toward Jerry Jones and Cowboys management), analytical breakdowns (Bears/Johnson/Williams), and features practical, behind-the-scenes perspective from Scott Pioli. Humorous asides and self-deprecation (especially from Jay) keep the tone lively and relatable (“I don’t hang out with anybody. I don’t have a life.” – Jay, 33:54).

In summary:
The episode offers a sharp, behind-the-curtain look at chronic Cowboys dysfunction, the challenge of marrying Caleb Williams’ style to Ben Johnson’s coaching in Chicago, and practical wisdom from Scott Pioli about player, team, and front office strategy in both pro and college football. If you're a football fan looking for context and insight on the season's biggest storylines, this episode is essential listening.