The Herd with Colin Cowherd: 3&Out - Caleb Williams REACTION, NFC West Preseason RECAP, Greg Olsen STOPS BY

Date: August 18, 2025
Host: John Middelkoff (on The Volume/iHeartPodcasts)
Special Guest: Greg Olsen (NFL veteran, Fox broadcaster)

Episode Overview

In this episode of "3 & Out," John Middelkoff dives deep into the preseason debut of Chicago Bears QB Caleb Williams, evaluates rookie QBs around the league, and recaps the NFC West preseason storylines. The show concludes with a thoughtful and candid conversation with Greg Olsen about youth sports, coaching philosophies, the impact of the transfer portal, and lessons learned from his playing and broadcasting career.

Key Discussion Points & Insights

1. Caleb Williams' Bears Debut – In-Depth Reaction

[03:16 - 21:00]

• Preseason Context: John acknowledges the caveats of preseason evaluation: variables like who's actually game-planning, which starters are playing, and so on.
• Setting the Scene: Williams' drive began with a botched kickoff, forcing him to go nearly the length of the field with his first-ever NFL preseason series.
• Ball Out Quick: The biggest past criticism of Caleb was that his timing might not translate from college to the pros. Middelkoff notes how, on his first drive, it was "ball snapped, ball out."

  “You're like, holy shit. That was the biggest question mark because we know Caleb has the big arm.” — John Middelkoff (08:24)

• Key Completion: Emphasizes the importance of a layered throw to Loveland, more so than the touchdown that followed.

  “I know the touchdown pass is like the sexiest play… but to me, that was the most important pass.” — John Middelkoff (09:35)

• Touch and Timing over 'Hero Ball': Winning in Ben Johnson’s offensive system is about timing and doing what’s schemed. Winners need to execute on schedule; Williams showed flashes of doing just that.
• Offensive Line Upgrades: Chicago prioritized interior OL to let their sub-6'2" QB step up — a proven recipe that Sean Payton used with Drew Brees.
• Pressure and Rhythm: Williams showed poise under pressure, delivering catchable balls and responding well to quick reads, critical for early-season tests.

Notable Quote:

“If Caleb can play on time and play in rhythm, we know this offense works — because we've just seen it.” — John Middelkoff (11:44)

2. Rookie QB Watch & Team Hope

[23:22 - 32:52]

• Hope as a Fan's Fuel: Middelkoff draws a parallel between the optimism triggered by new QBs and universal human hope.

  “There’s nothing more powerful than hope in life… the hope of a new quarterback is a powerful, powerful emotion.” (24:08)

• Titans (Cam Ward): Possibility to be a “sleeper," as Ward’s physical gifts could translate into 7–8 wins, a big step up from last year’s disappointment.
• Giants (Jackson Dart): Contrasts with Daniel Jones’ struggles; Dart passes the "eye test" even if the stats aren’t gaudy.
  • Throws with touch/layering = essential for NFL survival.
  • Notes the difference that coaching and development can make in careers (e.g., Alex Smith’s trajectory under Harbaugh and Reid).
  • Coaches often stick with the vet too long; fans and owners just want the rookie to play — and will lose patience with the Russell Wilson bridge experiment.
• Diversity of Physical Traits: Discusses how the NFL’s spread offense makes it harder to evaluate, but physical tools, intangibles, and toughness remain critical.

Notable Quote:

“If you can't layer the ball over a linebacker and under a safety, you cannot function as a quarterback in the NFL.” — John Middelkoff (27:16)

3. NFC West Preseason Recap

[32:52 - 54:19]

San Francisco 49ers

• Injury Bug Returns: “They gotta be near the top, if not leading the league in injuries.” (34:18)
• Kicker Drama: Third-round pick Jake Moody’s field goal struggles nearly cost him but a clutch kick might have saved his job… for now.

  “Sometimes you can hit five balls out of bounds and then finally stripe one down the middle. That might be the case here.” (37:25)

• Special Teams Neglect: “Kyle Shanahan despises special teams… but you do have to put some emphasis there.” (36:35)

Los Angeles Rams

• Matt Stafford’s Uncertain Health: Ongoing back issues leave the team in limbo; Garoppolo as contingency plan means a playoff push is unlikely.

  “If Jimmy Garoppolo is their quarterback, they have no chance to make the playoffs.” (41:40)

Arizona Cardinals

• Jacoby Brissett Backup: Odd fit as Kyler Murray's backup—their skillsets are opposites, possibly complicating scheme continuity if Murray is injured.

Seattle Seahawks

• Physical, Well-Coached, and a Threat: “If you just watch their intensity, their physicality… they could be a problem.” (45:12)
• Week 1 Showdown: Opening against a battered Niners team presents an early test of Mike Macdonald's culture shift in Seattle.

Division Outlook

• Surprise Potential: Middelkoff sees Seattle as a real threat to overtake the Niners if health and coaching trends continue.

4. NFL News & Front Office Insights

[48:30 - 54:19]

• Quarterback Uncertainty = Red Flag: Teams like the Colts without a named starter in mid–late August can’t be taken seriously as contenders.

  “If you do not know who your starting quarterback is in the middle to late August, you're just not — I can't take you seriously.” (51:01)

• Eagles Trade Talk: Howie Roseman’s aggressive approach, including a trade for John Metchie, and the team's ‘Alabama-to-Philly pipeline.’

Notable Quote:

“Sometimes you just don’t need to overthink this and just take good players from the best teams.” — John Middelkoff, paraphrasing Howie Roseman (52:13)

• Bryce Young’s Intangibles: Despite rookie struggles, Young’s character, toughness, and “mental makeup” may help him turn things around for the Panthers.

  “You can't underestimate, at quarterback, the importance of all the stuff that doesn’t get measured… how mentally tough you are, how smart you are.” (54:03)

Greg Olsen Conversation: Youth Sports, Coaching, & The Transfer Portal

[59:09 - 93:08]

Youth Sports & Parental Challenges

[59:33 - 64:11]

• Then vs. Now: Olsen reflects on how simple youth sports were in the '90s—play for your local team vs. today’s dizzying options, travel, and high-pressure environments.
• “Long-Term Development” is Core: When parents rush kids’ progress or team-hop for early wins, kids miss adversity, loyalty, and growth.

Notable Quote:

“When you race development, and when it's a race to 12 and a race to 13, you skip over a lot of really important steps.” — Greg Olsen (61:23)

• Multi-Sport Value: Playing multiple sports builds not just physical, but crucial mental skills.

  “There's a lot of movements in basketball that are really good carryover to football...” — Greg Olsen (64:24) “There’s something liberating about playing other sports where there are no expectations.” — Greg Olsen (65:06)

Coaching Philosophy and Real-World Lessons

[67:12 - 73:27]

• Coaching Middle School Football: Olsen coaches his son’s team hard, with a focus on effort, discipline, and learning through adversity.

  “We are not coaching any of these kids… to become professional footballers… If none of them do, it’s still all worth it. And that's the point.” (72:01)

• Life Lessons as the Real Goal: Leadership, accountability, work ethic, and showing up when it’s hard — football is a proxy for life itself.

Notable Quote:

“In the process of teaching these kids football, we're teaching these kids what life looks like. And that life is not vacation and life is not…always going to go your way.” — Greg Olsen (73:00)

The Transfer Portal & Changing College Football Culture

[73:27 - 85:35]

• ‘Mercenary’ Culture: Rampant transfers and player acquisition have eroded traditional values of team, loyalty, and working through adversity.

  “Everyone's just a mercenary, right?... Development is now secondary to player acquisition. Everything is just about player acquisition.” — Greg Olsen (74:29)

• Suggested Solutions: Olsen proposes allowing either NIL earnings or free transfers, but not both. Otherwise, college football becomes NFL free agency with no contracts.
• Depth Chart Reality: Top programs no longer plan for deep rosters. If you’re not second string, you’ll transfer — “Just trying to get to at least two deep.”
• Personal Story: Olsen describes his own redshirt year — developing on scout team vs. NFL-bound Miami defenses — as foundational to his growth.

From Tight End U to NFL Observations

[89:45 - 93:08]

• Tight End U: From a small get-together to the NFL’s premier offseason position summit, now headlined by Travis Kelce and Taylor Swift.
• Football Junkies: Top players are obsessed with their craft—development and improvement never stop, regardless of stardom.
• Broadcasting Insights: Olsen cherishes the unfettered access to head coaches and GMs, revealing which organizations are buttoned-up vs. those just “making it up.”
• Ongoing Ties with Coaches: Plenty of NFL coaches text back and forth not just about NFL schemes, but even middle school football.

Notable Quote:

“There's no good player that I've ever been around… that didn't wake up every single day fully consumed with the craft of improvement.” — Greg Olsen (91:22) “The day [the process of learning] ends is the day you stop playing.” — Greg Olsen (92:14)

Notable Quotes & Memorable Moments

• “I wish there were 32 teams with 32 sweet quarterbacks, because I'd rather have all these teams matter.” — John Middelkoff (20:42)
• “If Ben Johnson can figure out Caleb Williams, none of that shit matters [about front office dysfunction].” — John Middelkoff (14:30)
• “The idea of perpetual improvement and time, in forever—that’s the goal.” — Greg Olsen (92:24)

Timestamps for Key Segments

• Caleb Williams Bears Debut: 03:16 – 21:00
• Rookie QB Evaluations & Team Hope: 23:22 – 32:52
• NFC West Preseason Breakdown: 32:52 – 54:19
• Greg Olsen Interview Begins: 59:09
  • Growing up in youth sports: 59:33
  • Coaching philosophy: 67:12
  • Transfer portal & college football changes: 73:27
  • Broadcasting and NFL insights: 85:35 – 93:08

Summary

Middelkoff offers sharp, experience-based observations on the preseason, rookie QBs, and the complex dynamics of NFL rosters and coaching staff. His conversation with Greg Olsen is a heartfelt discussion on how youth and college sports have evolved, what kids and parents can learn from adversity, and why establishing a growth mindset transcends the sport itself. Their mutual appreciation for the game—both at its highest level and at its foundation—shines throughout.

For listeners who want an unfiltered, insightful look at football development from high school sidelines to NFL stadiums, and a pulse check on the 2025 preseason, this episode is essential.