The Windup: A Show About Baseball

Episode 191: The Roundtable | Interesting Manager/Front Office Hires & A Little Free Agency Talk

Date: November 7, 2025
Hosts: Grant Brisbee, Andy McCullen, Sam Miller

Overview

This episode of The Roundtable dives into recent surprising hires in MLB front offices and managerial positions, specifically focusing on the Colorado Rockies hiring Paul DePodesta. The hosts debate the implications of such unconventional choices and discuss the evolving criteria for MLB managers today. They also break down early trends and uncertainties of the 2025-2026 free agency period, reflect on “the death of the fundies” (i.e., modern baseball fundamentals), and close with some baseball trivia and lighter banter.

Key Discussion Points and Insights

1. The Rockies Hire Paul DePodesta: A Throwback or a Visionary Move?

• Background: The Rockies hire Paul DePodesta, famous for Moneyball-era innovation, but most recently a Cleveland Browns (NFL) executive.
• Hosts’ Immediate Reactions:
  • Grant: "If you hire Paul DiPodesta in 2025, that does kind of feel like you are living 20 years in the past." (02:32, Andy)
  • Andy: "That's not to say that he can't do the job...he's got a wealth of experience in a variety of different endeavors." (02:41)
  • Sam likens the hire to inviting a celebrity outsider: “He feels like the Eddie Vedder for the Rockies” (05:15)
• Unusual Candidate Pool:
  • Both Amiel Sawdaye and Matt Forman, considered front-runners, turned down the job.
  • The hosts speculate this left DePodesta as the “third choice” rather than the “celebrity get” (05:48, Sam)
• Is DePodesta an Asset or Outdated?
  • Grant argues DePodesta’s game experience predates the modern “statcast” revolution; maybe that’s an advantage for conquering altitude’s unique challenges:
    • "Maybe the person who fixes the Rockies has to ignore that and get back to patient zero of how do you win at altitude?" (08:39)
  • Andy and Sam note uncertainty—nobody knows what DePodesta actually thinks about today's game, and his “currency” might be obsolete.
    • "He could be thinking that second baseman still bat second… that’s the time period he came of age." (07:18, Andy)
• Motivation Behind the Move:
  • Is this DePodesta seeking an intellectual challenge akin to “Theo Epstein fixing the Rockies”?
    • “It feels like an intriguing challenge for him, but it’s not clear whether it works or not.” (10:27, Sam)

2. Evolving Criteria for MLB Manager Hires

• Context: Recent managerial searches have included oddball names, ranging from Albert Pujols to high school experience guys. (11:54, Sam)
• What Makes a Good Manager Now?
  • Andy: "I think the pool of managerial candidates is probably pretty wide" (13:14)
  • Modern clubs prioritize a mix of experience, player development acumen, relationship skills, and adaptability.
    • "It's a sort of role that shifts with each and every day ..." (13:44, Andy)
  • Grant: "Is there any qualification left besides managing personalities?" (18:00)
  • Andy: "Can you work with your GM? Do your stars like you? Do you understand what leverage is?" (17:18)
• Special Assistant-to-Manager Pipeline:
  • Growing trend for "special assistants" or ex-players hanging around to ascend to the job, sometimes unexpectedly. (14:33, Andy)
• Transition to Player Development Model:
  • Sam and Andy discuss player development at MLB level taking on a "college coach" model, with managers leading a group of coaches shepherding the on-going development of big leaguers.
    • "I think that the idea is to build ... kind of a player development culture at the big league level, which is more in line with what you would expect from a college program." (18:48, Sam)
  • Andy: "I mean, I think that's part of it. Way more so than it used to be." (19:12)

3. 2025-2026 MLB Free Agency Uncertainties

• Early Contract Predictions Feel 'High'
  • Grant is surprised by Tim Britton’s projected contracts, given recent trouble for stars like Bregman and Alonso finding deals. (21:27)
• Market Skepticism:
  • Andy: "I don't know who's going to be paying them." (22:13)
  • Sam: "You're always kind of looking for clues in the first few transactions and you can overreact to them..." (24:22)
• Possible Bear Market:
  • Andy predicts a bearish winter: "I think it might be bearish. I think it might be grizzly, as they say." (23:10)
• Effects of Potential Work Stoppage/Lockout:
  • Discussion: Does the prospect of a 2027 lockout create reluctance for long-term contracts this year?
  • One-year “pillow” deals are less attractive now—players don’t want to face free agency in a lockout year.
    • "That's not going to be as appealing to players this year because they don't want to opt out 12 months from now and then have to negotiate with the lockout." (26:12, Sam)
• Market Specifics and Puzzling Decisions:
  • Cubs let Shota Imanaga walk instead of picking up a seemingly reasonable 3-year $57 million option.
    • Grant: "Unless the Cubs have video of that Twilight Zone gremlin rummaging through his arm... I don't get where this... helps anyone." (30:25)
  • Teams seem reluctant; even strong “middle-market” contracts (e.g., Imanaga, Jack Flaherty, Shane Bieber) are being refused or met with caution.
• Pillow Contract Glut:
  • Andy and Sam discuss the market being flooded with mid-level pitchers and a general reticence for longer-term deals.
    • Andy: "There's not many guys on this market who you'd feel really good about giving a five year contract to as a pitcher..." (28:00)
• Qualifying Offers, Sunk Costs, and Team Accounting:
  • The hosts riff on the strange accounting logic of qualifying offers and mutual options, and the “sunk cost fallacy.”
    • “They're not paying Brandon Woodruff $32 million. They're paying old Brandon Woodruff, who's... long gone, never coming back." (36:35, Sam)

4. The Death of Baseball Fundamentals (“The Fundies”)

• Sam’s Rant and Theory:
  • Sam has "been sort of losing my mind over the death of the fundys this year." (37:51)
  • Players are worse at baserunning, outfield assists, fielding—he blames multi-position development and, brilliantly, poorly-fitted helmets.
    • “They're running around with loose helmets, and I think it's driving them slowly insane.” (39:04, Sam)
• Evidence for Helmet Hypothesis:
  • Andy and Grant enthusiastically agree.
  • “They are not wearing properly fitted helmets.” (40:06, Andy)
  • “The helmet is like lapping itself...they are wearing your dad’s suit loose.” (40:22, Sam)
  • "My all timer helmet moment is...Dom Smith’s helmet came off on a home run trot." (43:07, Sam)
• Implications:
  • Once seen, this is “unseeable” and the hosts name it “The Miller Theorem” (46:23, Grant)
  • Sam: “Good. Yeah, let’s do this.” (46:25)

5. Closing Banter and Trivia

• Annual Dodgers Bit:
  • “They did their now annual tradition of getting tanked and going on Mookie Betts's podcast. Not many headlines this time." (46:26, Andy)
• Justin Dean’s Unique Stat:
  • "Justin Dean: more World Series rings than career hits." (47:00, Sam)
  • Leads to a fun riff about Travis Gore, Raul Mondesi Jr., and Herb Washington’s hitless championship.

Notable Quotes & Memorable Moments with Timestamps

• “[On DePodesta]: When you hire Paul DiPodesta in 2025, that does kind of feel like you are living 20 years in the past.” — Andy (02:32)
• “He feels like the Eddie Vedder for the Rockies.” — Sam (05:15)
• “Maybe the person who fixes the Rockies has to ignore that and get back to patient zero of how do you win at altitude?” — Grant (08:39)
• “You need someone to manage the vibes. Nope, you need someone to...There’s no consensus now.” — Grant (15:25)
• “Can you work with your GM? Do your stars like you? Do you understand what leverage is? All right, you’ll get in the door.” — Andy (17:18)
• “It’s a very amorphous job at this point.” — Andy (17:33)
• “Every left fielder, they have not made a good throw in three years. Not one good throw.” — Sam (38:32)
• “They’re running around with loose helmets, and I think it’s driving them slowly insane.” — Sam (39:04)
• “The helmet is like lapping itself…They are wearing your dad’s suit loose.” — Sam (40:22)
• “My all-timer helmet moment is in... Dom Smith’s helmet came off on a home run trot.” — Sam (43:07)
• “Justin Dean: more World Series rings than career hits.” — Sam (47:00)

Timestamps for Key Segments

• [01:32] — Episode intro, banter
• [01:59-10:27] — Paul DePodesta hire: analysis, historical context, implications for Rockies
• [11:54-19:18] — Evolution of MLB manager hiring, special assistant trend, what now makes a good manager
• [21:27-34:16] — MLB Free Agency: market trends, pillow contracts, team motivations, puzzling deals
• [37:51-46:25] — Sam’s "Death of the Fundies" rant: defensive fundamentals, helmet theory, banter
• [46:26-48:41] — Dodgers podcast joke, trivia about Justin Dean & rare career stats

Takeaways

• The Rockies’ hiring of DePodesta is viewed mostly as a fascinating, unconventional gamble in a time where the industry is showing a penchant for weird, nontraditional hires in both front offices and manager seats.
• There is no longer a clear manager archetype; adaptability, relationship skills, and player development ethos now supersede résumés.
• Free agency is clouded by looming labor concerns and team caution; expect shorter, more cautious deals, especially for pitchers.
• The “death of fundamentals” is becoming more evident, in part due to player multi-positioning and… helmet fit.
• The episode balances sharp analysis with humor, side stories, and the distinctive camaraderie of the hosts.

For those who missed the episode:
This podcast captures a snapshot of an MLB winter that feels transitional and uncertain, with teams and players alike navigating new realities—both on the field (or basepaths) and in negotiations. The loose-helmet theory may or may not change your life, but you'll never watch a baserunner the same way again.