The Windup: Starkville | Ken Rosenthal Reviews the Insane Dodgers World Series Victory & Previews MLB Free Agency

Podcast: The Windup: A show about Baseball
Host(s): Jayson Stark, Doug Glanville
Guest: Ken Rosenthal
Date: November 5, 2025

Episode Overview

This episode of Starkville features Jayson Stark and Doug Glanville in conversation with Ken Rosenthal, fresh off what many are calling the greatest World Series ever. They provide a lively, deep-dive recap of the unforgettable Dodgers-Blue Jays seven-game classic—analyzing pivotal plays, unsung heroes, and the grandeur of Game 7—before turning their focus to the burning questions of MLB free agency and the upcoming off-season. Throughout, the trio reflect on the emotional, improbable, and uniquely baseball moments that defined the 2025 series.

Key Discussion Points & Insights

1. The World Series: A Game for the Ages

[02:43–21:49]

• World Series Recap and Signature Moments

  • Doug and Jayson marvel at the drama and escalating intensity of the series, especially its climactic Game 7.
  • Notable Moment: Miguel Rojas' defensive heroics and ninth-inning game-tying home run.
    • Doug highlights “the true team spirit of baseball” and how unexpected contributions defined the series.
    • Jayson: "Think of how slim the difference was between winning and losing that game, which means also between winning and losing that World Series." [13:39]
  • The crew discuss the pivotal play in the bottom of the ninth, with a conservative baserunning decision (IKF) by the Blue Jays, possibly costing them the championship.
    • Insights into baserunning risk/reward strategy, and the psychological impact of the previous game’s walk-off double play.
    • Doug: "It was really about a risk assessment before the play even happens. ... He was definitely conservative and that extra two feet was the difference." [08:50]

• Game 7 Breakdown

  • Rosenthal, reporting from the dugout, recalls witnessing a “crazy, unusual, unforgettable” Game 7.
    • Ken: "Rojas, to me, I guess, would be the most memorable... But even Max Scherzer doing what he did, there were so many things, and that's what's unique about this World Series." [16:44]
  • Players like Ohtani, Guerrero, and Savage are singled out for their all-time performances.

• Unpredictability and Second-Guessing

  • The group reflect on how each play could have swung baseball history.
  • “Every play it seemed like it was like, well, what if he did this? What a series.” – Doug [13:20]

2. Was This the Greatest World Series Ever?

[23:52–30:10]

• World Series in Historical Context
  • Ken ranks this series #3 since 1987, behind 1991 and 2001, but admits it could be #1 due to the depth and variety of storylines.
    • "All those individual performances, all the crazy things we saw, that might be, in my opinion, too, why this is number one." – Ken [29:14]
  • Doug emphasizes the diverse, international cast and improbable narratives, from Ohtani’s on-base streak to rookies starring on the big stage.
    • “There was storyline after storyline that just made me go, what in the world is going on?” [26:28]
  • Jayson suggests when the dust settles, "we might just do what Doug Glanville just suggested and say this was the greatest World Series ever." [28:27]

3. Behind the Beat: The Life of a Baseball Writer/Broadcaster During the Series

[30:10–35:32]

• Personal Stories from the Trenches
  • Jayson and Ken share grueling details of working the World Series: endless late nights, sleep deprivation, and the intense schedule of reporting and writing.
    • “National Sleep Deprivation Month. And that is what October is.” – Ken [33:40]
    • “My favorite part of my job is we get to see things that people talk about for the rest of their lives and we get to tell those stories.” – Jayson [34:22]
  • Ken details the preparation, clubhouse routines, and challenges of juggling dual broadcast and writing duties during the postseason.

4. Free Agency & Offseason Storylines

[35:32–54:59]

• Top Free Agency Questions

  • Ken sees Tarik Skubal as the most interesting potential trade piece, drawing comparisons to the Corbin Burnes trade but notes the Tigers are carefully weighing their options. [36:06]
    • Clubs like Mets, Phillies, Yankees, and Dodgers are potential suitors.
  • Sandy Alcantara’s trade likelihood is discussed—Marlins may hold for now, hoping his value rises with better performance. [38:01]
  • Doug and Ken look at the Dodgers' strategy for a possible three-peat, considering the aging core and potential targets like Kyle Tucker and Bo Bichette. [39:50, 40:48]
    • On Bo Bichette: “He is a really outstanding offensive player. I expect that he's going to do well because teams will say, okay, but we'll take you at second or we'll take you at third. It's just that if he's hung up on shortstop, he's going to have a problem.” – Ken [41:09]
  • Discussion around Alex Bregman’s value and Boston’s potential pursuit, noting Scott Boras’ negotiating leverage: “If Boston offered, say, six years, $210 million, that's the floor. Let's go.” – Ken [46:48]
  • Pete Alonso’s situation in New York: Ken doesn’t believe David Stearns is inclined to commit long-term, but Alonso (without a qualifying offer) is in a favorable spot as a power bat on the market. [47:38, 48:01]
    • Doug: “I would try [to keep him]. I would absolutely try … but trying with Scott Boras is tough because it's not gonna be cheap.” [49:02]

• Phillies’ Offseason Needs

  • Ken and Jayson agree the Phillies will likely re-sign Schwarber, but question where funds will come from for added young offensive talent. Bregman and Bohm’s future are considered pivotal. [50:15]
  • On organizational limits: “John Middleton is enthusiastic … but there has to be a limit, and they've got to be getting somewhat close to that limit.” – Ken [52:26]

• Possible Fallout Around Bryce Harper & Phillies Management

  • Doug asks about Dombrowski’s pointed comments regarding Harper. Jayson senses Dombrowski used the media to send Harper a deliberate message, adding intrigue to the Phillies’ chemistry and offseason moves. [52:56]
  • Ken: “I wondered at the time if this was simply Dave saying to Bryce and Scott, 'Stop asking me for an extension. Shut up and play now.'” [54:58]

5. Strange But True: Oddities from the 2025 Series

[56:58–67:11]

• Treaus Savage's World Series Breakout
  • A pitcher barely known months ago strikes out 12 in a World Series game—matching his previous 12-strikeout game against only 494 fans in the minor leagues.
    • “So pretty much the same thing, Doug, wouldn't you say?” – Jayson [58:54]
• The $1.2 Billion Home Run
  • Vlad Jr.'s home run off Shohei Ohtani is, by contract value, possibly the most expensive home run in history. [59:56–61:03]
• Miguel Rojas' Game-Tying Homer: A Baseball Miracle
  • Rojas, with scant power and little playoff playing time, becomes the first ever to hit a game-tying homer in the 9th inning of a Game 7—his only previous home run off a righty all year was against a position player.
    • “So what made it so strange but true? … He didn’t have a hit in a month, hadn’t started in weeks, hit one home run since July… and then that guy hit the first game-tying home run in the ninth inning of any World Series game ever played.” – Jayson [64:13]

Notable Quotes & Memorable Moments

• On the spirit of the Series:
  "That series was such a great representation of baseball at its best…every play was like the end of a chapter that could have been a movie."
  – Doug Glanville [03:11]

• On risk assessment at third base:
  “It was really about a risk assessment before the play even happens. … He was definitely conservative and that extra two feet was the difference.”
  – Doug Glanville [08:50]

• On the Game 7 crescendo:
  "Game 7 in our sport is unlike any game 7 in any other sport. Because the stuff that happens is so far outside the box, like you couldn't even think of it, let alone draw it up."
  – Jayson Stark [19:56]

• On Migel Rojas and clutch defense:
  "He selflessly taught Mookie Betts how to become a Gold Glove candidate against impossible odds... and then to do it in the World Series and then show like, oh, by the way, defense is really important."
  – Doug Glanville [17:44]

• On evaluating this World Series historically:
  “All those individual performances, all the crazy things we saw, that might be, in my opinion, too, why this is number one.”
  – Ken Rosenthal [29:14]

Timestamps for Key Segments

• [02:43] – Podcast proper begins; World Series amazement
• [05:12] – Deep-dive on Game 7 ninth-inning play and baserunning
• [13:39] – Slim margins and multitude of narratives in Game 7
• [16:44] – Ken Rosenthal reflects from the dugout
• [24:12] – Was this the greatest World Series ever? Historical comparisons
• [30:10] – Life of a baseball reporter during the Series/Postseason
• [35:32] – Offseason preview: Key trade and free agent targets
• [41:09] – Bo Bichette’s free agency and defensive future
• [46:48] – Scott Boras, Alex Bregman, and Red Sox pursuit
• [50:15] – Phillies’ offseason outlook and constraints
• [52:56] – Bryce Harper, front office dynamics, and possible fallout
• [56:58] – ‘Strange but true’: Unsung heroes and oddities from the Series
• [64:13] – Breaking down Migel Rojas’ historic, improbable home run

Conclusion

This episode will delight any fan looking for a thoughtful, passionate breakdown of the 2025 World Series’ chaos and magic, as well as a primer on the rapidly approaching free agency drama. The hosts’ blend of analytics, anecdote, and humor—paired with Ken Rosenthal’s authoritative reporting—keep both the magic of baseball and the intrigue of its business at the forefront, all rendered in their characteristic camaraderie and wit.

For more compelling baseball conversation, subscribe to The Windup or follow Jayson Stark, Doug Glanville, and Ken Rosenthal at The Athletic.

Note: Timestamps exclude commercials and non-content sections.