The Windup: The Roundtable | Dodgers Comeback to Win Their 2nd Straight World Series

Podcast: The Windup: A Show About Baseball
Episode: 190 – The Roundtable | Dodgers comeback to win their 2nd straight World Series
Date: November 3, 2025
Host: Grant Brisbee
Panelists: Andy McCullough, Sam Miller

Overview

This episode dissects the thrilling 2025 World Series in which the Los Angeles Dodgers staged a comeback to capture their second consecutive championship, defeating the Toronto Blue Jays. Grant Brisbee, Andy McCullough, and Sam Miller break down the series' most dramatic moments, the narrative arcs of both teams, and the legacy questions this series brings for the Dodgers and baseball as a whole. The conversation delves into game strategy, key plays, historical context, team culture, and what the result means for both organizations moving forward.

Key Discussion Points and Insights

1. Was This the Greatest World Series Ever?

• Ranking the Series

  • Sam Miller shares his updated all-time rankings, placing this series somewhere between 4th and 7th best ([02:27]):

    “As I have previously written, 9,000 words ranking every World Series... I have it somewhere between four and seven, maybe five and seven for context.” – Sam Miller

  • Panelists debate against recency bias and compare recent classic series: 1975, 1991, 1986, 2011, and 2016 ([02:56], [03:11]).

• Greatest Games Within the Series

  • Two of the 10 greatest games ever occurred in this World Series, according to Sam ([03:32]).

2. Comparisons to Historic Series & Game 7 Moments

• 2016 vs. 2025 Game 7

  • Andy: Remembers 2016 for a couple iconic moments (Raja Davis HR, the rain delay), but felt the 2025 finale had even more “skull crushing tension” in the final innings ([05:06]).
  • The sense that every player on the Blue Jays contributed both to the breakthrough and the heartbreaking loss ([06:12], [06:42]).

• Play Detail and Ephemera

  • Grant notes those “texture plays” that stick with the immediate viewer, like the line drive to Max Muncie in the 8th—ephemeral but defining ([03:32]).

3. “The Better Team Didn’t Win” & The Nature of Baseball’s Fairness

• Caleb Joseph's Post-Game Comments

  “You know, you guys saw Caleb Joseph, you know, come out in the postgame, and he opened it with, like, you know, the better team didn't win. And, you know, he said, sorry if that's sour grapes, but that's what I feel.” – Sam Miller ([08:33])

  • Wrestling with definitions of “better team”—Sam describes the Blue Jays playing at the peak of their abilities, and the Dodgers at a low percentile, yet the Dodgers’ built-in advantage prevails.

• Sisyphean Challenge and Recurring Dodgers/Giants Dynamic

  • The panel equates the experience to facing a seemingly unbeatable “final boss” ([09:40]).
  • Echoes of the 2021 Giants–Dodgers race: “There’s, like, a final boss you can’t get past, even when he’s barely trying.” – Sam Miller

4. Dodgers Culture, Dynasty, and Comparison to the Yankees

• Yankees Parallels

  • Andy sees growing similarities with the late 90s–early 2000s Yankees—winning not with overwhelming regularity but always knowing “how to win” ([10:46]):

    “The Dodgers know how to win baseball games like this. They have demonstrated it over the last couple of years when... they're old and they're hurt and they're tired, they know how to win the game.” – Andy McCullough

• Talent and Self-Sacrifice

  • Discussion of the Dodgers’ culture: unselfish stars, e.g., Mookie Betts moving to shortstop, Freddie Freeman playing through injury for the team ([15:20]).

  • “It’s a culture within the organization of self-sacrifice... But I do think it's worth considering that the Dodgers selected some of these players for nine figure contracts because they felt like they would be willing to self-sacrifice at various times.” – Andy McCullough ([16:26])

5. Game Seven’s Heroes and Strategic Decisions

• Yoshinobu Yamamoto’s Heroics

  • The crew marvels at Yamamoto’s performance and durability, considering his stature and the era’s focus on bullpen usage ([12:47]):

    “He was his own bullpen.” – Grant Brisbee “Beyond Randy Johnson. And he's a foot shorter.” – Andy & Sam

  • Yamamoto’s presence in the bullpen may have subtly influenced relief decisions, such as Will Klein's pitch selection ([17:57]).

• Contingency and Tipping Points

  • The unending string of “what-if” moments in Game 7:

    “Game seven was just tipping point after tipping point and sliding door after sliding door after sliding door… 500 million different alternate histories in that one game alone.” – Grant Brisbee ([18:53])

• Key Defensive Plays

  • Dissection of the 9th- and 10th-inning high-wire plays:
    • The Rojas force out at home, followed immediately by the Pajes game-saving catch in the outfield ([24:57]):

      “That catch is part of baseball lore... Did Pajes do the right thing? There was conviction in his... he was willing to truck Kiki Hernandez and that's the only way that he catches the ball.” – Grant Brisbee ([26:14])

    • Ongoing debate about Isaiah Kiner-Falefa’s base running and the fairness of scapegoating him for the loss ([28:11]).

• Depleted Rosters and Fatigue

  • Both teams played with visible exhaustion, magnifying the execution level in Game 7 ([32:42]):

    “They were all just looked exhausted, you know, and that's kind of what made the level of execution and talent in those final games so riveting.” – Andy McCullough

6. Managerial Sliding Doors & Missed Opportunities

• Many “sliding door” moments, e.g.,
  • The 3-0 pitch to Vlad from Snell in the 9th ([34:41]).
  • Not using Kershaw in relief and his humorous lost sense of game status ([39:01]):

    “He had lost track of the outs... Kershaw, like, gets the ball back and it's like, all right, I'm going in. And Josh Barton, coach is like, we won the World Series. Are you sure? Oh, okay, great.” – Andy McCullough

7. Dodgers’ Build and Replicability

• Starter Depth as a Model

  • Dodgers used seven pitchers in the final two games—five of whom began the year as starters ([41:09]).
  • Emphasis: “The Dodgers really proved that all relievers are unreliable and that the best you can hope for is to have way too many starters available...” – Sam Miller

• Will This Model Spread?

  • Acknowledged as perhaps unique to the Dodgers’ immense resources ([42:04]).
  • Speculation about Dodgers continuing their dominance ("the only team that matters"?) into 2026 ([42:18]–[44:59]).

• Aging Core vs. Youth Conveyor Belt

  • Concerns about the aging of Betts, Freeman, and others. Panelists note the Dodgers' deep farm system provides potential future stars ([44:01]).

• Potential Offseason Moves

  • Discussion about Kyle Tucker, Tarek Skubal, and the front office’s “optionality” ([45:18]–[47:19]).

8. Yamamoto’s Legacy and Awards

• Will this playoff put Yamamoto in the running for Ace votes, possibly even unanimously? Panelists discuss the voting quirks and his postseason workload ([48:37]–[50:19]).

9. Empathy and Heartbreak: The Blue Jays’ Perspective

• Emotional trauma and humiliation for Blue Jays players and fans:

  “The Blue Jays are just gonna be sitting on the curb with Linus Van Pelt next to them. Just thinking of all the what ifs. Brutal.” – Grant Brisbee ([52:00])

  • Sam Miller’s reflection on losing:

    “Anytime you lose to another person, it's humiliating... that's what's so painful about this for the Blue Jays is they 100% deserve no humility here. Like they shouldn't have to feel beat.” – Sam Miller ([52:26])

• Comparison to “Breaking Bad”: Even when you get a heroic moment, the ending isn’t always happy ([53:17]).

Notable Quotes and Memorable Moments

| Time | Quote | Speaker | |---------|-------|---------| | [02:27] | “I have it somewhere between four and seven, maybe five and seven for context.” | Sam Miller | | [06:42] | “Every player was essential in getting them to Game seven of the World Series, and every player was essential in them losing the World Series.” | Andy McCullough | | [09:40] | “There's a final boss that you just can't get past, even when he's barely trying.” | Sam Miller | | [10:46] | “The Dodgers know how to win baseball games like this... when they're old and they're hurt and they're tired, they know how to win the game.” | Andy McCullough | | [12:47] | “He was his own bullpen. He was, he was freaky.” | Grant Brisbee, on Yamamoto | | [17:57] | “I just keep thinking he probably doesn't throw that curveball if Yamamoto is not in the bullpen...” | Ryan Reynolds | | [18:53] | “Game seven was just tipping point after tipping point and sliding door after sliding door after sliding door...” | Grant Brisbee | | [24:18] | “Everything was a goose biting people while they're trying to watch the Smashing Pumpkins.” | Grant Brisbee (humorous analogy for Game 7 tension) | | [26:14] | “He was willing to truck Kiki Hernandez and that's the only way that he catches the ball.” | Grant Brisbee, on Pajes’ catch | | [32:42] | “They were all just looked exhausted...and that's kind of what made the level of execution and talent...so riveting.” | Andy McCullough | | [39:01] | “[Kershaw] had lost track of the outs...Coach is like, we won the World Series. Are you sure? Oh, okay, great.” | Andy McCullough | | [41:09] | “The Dodgers really proved that all relievers are unreliable and that the best you can hope for is to have way too many starters available...” | Sam Miller | | [50:59] | “Loved this team. One of my favorites. One of my favorites. And what a great postseason, you know, run.” | Ryan Reynolds, on Blue Jays | | [52:00] | “The Blue Jays are just gonna be sitting on the curb with Linus Van Pelt next to them. Just thinking of all the what ifs. Brutal.” | Grant Brisbee | | [52:26] | “They 100% deserve no humility here...they shouldn't have to feel beat. They played so friggin well...” | Sam Miller |

Timestamps for Important Segments

• Series greatness and historical context: [02:06] – [06:42]
• Dodgers’ intangibles and dynasty talk: [10:46] – [15:16]
• Yamamoto’s performance and game seven breakdown: [12:47] – [20:25]
• Game 7’s wildest moments & defensive plays: [24:18] – [28:11]
• Fatigue, sliding doors, and clutch vs. luck: [32:42] – [39:41]
• Dodgers 'model' and implications for future roster construction: [41:09] – [44:59]
• Dodgers' future, player contracts, and farm system: [45:00] – [48:37]
• Yamamoto’s legacy and votes: [48:37] – [50:19]
• Blue Jays’ heartbreak, emotion, and baseball’s 'lesson': [50:48] – [54:09]

Final Thoughts

• The 2025 World Series will be remembered for its high drama, countless sliding doors, and as yet another chapter in the Dodgers’ evolving dynasty.
• The Dodgers’ edge is part roster, part culture—winning without necessarily playing their best, thanks in large part to organizational depth, culture, and high-profile stars willing to embrace team-first roles.
• The Blue Jays’ defeat—a mix of heartbreak and pride—serves as a reminder of baseball's randomness and the agony of coming up just short, despite playing at the absolute apex of their abilities.
• The episode is peppered with humor, analogies, and personal anecdotes, bringing listeners right into the rollercoaster of emotions that defined one of the best World Series of this era.

For listeners who missed the episode, this rich roundtable captures the nuance, tension, and enduring questions from an all-time classic Fall Classic—and sets up the hot stove debates to come.