Podcast Summary: The Windup — The Roundtable | The Phillies & Yankees are eliminated

Podcast: The Windup: A show about Baseball
Hosts: Grant Brisbee, Andy McCullough, Sam Miller
Date: October 10, 2025
Episode: 183

Overview

In this lively episode of "The Windup" Roundtable, Grant Brisbee, Andy McCullough, and Sam Miller break down the elimination of the Philadelphia Phillies and New York Yankees from the postseason. The conversation dives deep into crucial moments that defined both teams’ exits, particularly focusing on the infamous Orion Kirkring play for the Phillies, the psychology of failure under pressure, comparative postmortems of the Phillies and Yankees, managerial decisions, Dodgers’ postseason narratives, and analytical riffs on playoff trends, identities, and fundamentals.

The tone was classic Roundtable—wry, analytic, self-deprecating, and deeply invested in both the mechanics and vibes of baseball’s biggest moments.

Key Discussion Points & Insights

1. The “Orion Kirkring Play” and the Human Element in Baseball

• [02:00-06:38]:
  The hosts open by discussing Phillies reliever Orion Kirkring’s critical error—coined “Orion’s Boner”—which became a flashpoint for assessing pressure and failure in baseball.

  • Sam Miller reflects on the psychology:

    “The worst thing that you can do is fail. Interestingly.” (02:21)

    “His internal clock is severely messed up by all the adrenaline and the stakes of the situation… he’s got tunnel vision… it’s just not going to be [calibrated].” (03:50)

  • Andy McCullough highlights empathy:

    “[Fans forget] there’s humans who play this game. I panic ordering dinner at restaurants—human beings panic. And like, it’s just… sad.” (04:33)

  • The group explores how rare such clear “panic moments” are at the major league level due to self-selection, but notes that “these are not generalists; they’re extraordinary at a narrow set of skills." (07:02)

2. Fundamentals & the “Wheel” Play Discussion

• [09:06-12:22]:
  The classic “Wheel” play during a bunt attempt by the Dodgers is dissected. Sam and Andy debate whether such fundamental plays are truly rare or just underappreciated.

  • Sam: “If you explain the wheel to a child, they’re gonna get it on the first try… I was surprised so many people were freaking out about the wheel—when pitchers still hit, you’d see it all the time.” (09:12, 09:45)

  • They praise the Dodgers’ infield defense and point out Nick Castellanos’s base running miscue.

    “His lead was… it wasn’t the aggressive lead you needed there.” (10:37)

  • Brief tangent about whether the Dodgers truly do or don’t practice the wheel in spring training (spoiler: likely, yes).

3. Postmortems: Phillies vs Yankees Eliminations

• [12:22-15:33]: The narrative shifts to analyzing the perspectives and futures of the Phillies and Yankees after another postseason disappointment.

  • Andy contrasts the two:

    “You don’t look at [the Yankees] as like, ‘Okay, there needs to be wholesale changes.’ Phillies… It’s hard to keep running into the same brick wall and not, you know, making changes.” (13:00)

  • Phillies’ owner John Middleton and president Dave Dombrowski’s “urgency” for a title is noted.

  • Grant draws an analogy:

    “If you’re going to jump into that [Buffalo Bills] category, why not do it on a ball that’s hit back to the pitcher? It’s almost like the end of … the Phillies dynasty we knew.” (14:51)

4. Process Evaluation & The Nature of Postseason Failure

• [15:33-19:06]:
  Sam brings up Jason Stark’s stat that the Phillies’ win total has risen seven years in a row (15:46), and the group weighs whether consecutive near-misses are a “failure of process” or just variance.

  • Sam:

    “It came down to a pitcher error, which is one of the hardest things to control for in baseball… I don’t want to say this era… has been marked by incompetence… It’s been a really solid team.” (15:44-17:00)

  • The Yankees, they argue, may “look worse" coming out, despite similar fates.

5. Managerial Decisions: Dave Roberts & the Dodgers

• [19:33-24:28]:
  The hosts do a mini deep-dive on Dave Roberts’ sometimes-questioned postseason maneuvering, particularly around bullpen deployment and starter usage.

  • Debates about:

    • Game 2: Using Trinen instead of Sasaki.
    • Game 3: Letting Kershaw stay in during a blow-up.
    • Game 4: Managing Sasaki’s workload.

  • Andy on Roberts' approach:

    “They're trying to… build the plane while flying it… It’s not gonna look normal... they don’t have a best three relievers… It’s going to look strange and when it goes sideways, there’s going to be egg on Dave’s face. But… I’m not totally sure what the right choices are." (21:51-24:24)

6. How Inevitable Are the Dodgers? Ohtani, Pitching Depth, and Future Rounds

• [24:49-32:24]:
  The talk pivots to whether the Dodgers’ apparent vulnerability undermines their status as favorites.

  • Ohtani’s “slump” and future outlook.
  • Importance of lefty pitching against LA’s lineup.
  • On why the Dodgers can look mediocre during stretches:

    “They have just fundamentally decided the regular season does not matter… every decision is made towards how can we be healthy on October 1st and we do not care how ugly it looks at various times during the year.” (31:43)

7. Team Postseason Identities & Analytical Riffs

• [32:56-34:58]:
  Sam admires how postseason pressure amplifies small regular season distinctions into huge factors—like the Blue Jays’ “never striking out” identity. Shows how team strengths (or quirks) can become postseason difference-makers.

  • Blue Jays’ low strikeout numbers and throwback play celebrated.

  • Grant:

    “When you look at the Blue Jays’ 2025 [stat] page and you go to that strikeout column—there’s two guys who struck out more than 100 times on that roster… you just don’t see that in the modern era. And I freaking love it.” (34:28)

8. Notable Quotes & Memorable Moments

• On failure and compassion:

  “I panic ordering dinner at restaurants—human beings panic. And like, it’s just… sad.” (Andy, 04:33)

• On postmortem framing:

  “The trajectory… it’s hard to point fingers and say [the Phillies are] not doing their job right. They lost a five-game series to a great team and it came down to a pitcher error, which is like one of the hardest things to control for in baseball.” (Sam, 15:44)

• On the Dodgers’ approach:

  “Every decision is made towards how can we be healthy on October 1st and we do not care how ugly it looks…” (Andy, 31:43)

• On the postseason amplifying identity:

  “A team… picks up an identity in the regular season because they’re 5% more of something than other teams… the postseason shows up and that, like, 5% difference becomes, like, 50%.” (Sam, 32:56)

Timestamps for Important Segments

• [02:00] – Start of Phillies/Orion Kirkring discussion
• [09:06] – The “Wheel” play, bunts, and fundamentals
• [12:22] – Phillies and Yankees: postmortem and contrasts
• [15:46] – Phillies’ seven-year win trajectory (Jason Stark stat)
• [19:33] – Debating Dave Roberts’s postseason decisions
• [24:49] – Assessing Dodgers’ championship inevitability
• [32:56] – Blue Jays’ identity and postseason amplification
• [34:28] – Team statistical quirks and nostalgia

Episode Tone & Final Thoughts

Fans of The Windup will find this episode quintessential: equal parts analytics, banter, in-jokes, and big-picture perspective. The trio manage to dissect, eulogize, and roast with equal affection—using detailed examples, memorable metaphors, and frequent appeals to baseball's deep emotional currents ("grandma's cookies" and "panic leaking out of ears").

The constant shifting between granular analysis and big-picture takeaways means even casual listeners will leave feeling smarter about both what happened and why it resonates.

For Further Listening

Skip the last two minutes if only interested in game analysis—the rest features meta-commentary about the show’s theme music, inside jokes, and a goofy behind-the-scenes segment.

Summary prepared by:
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