The Windup: The Roundtable | Clayton Kershaw Retires & Tight Races Down the Stretch

Episode 178 | September 22, 2025
With Grant Brisbee, Sam Miller & Andy McCullough

Episode Overview

This episode of The Windup dives deep into the seismic news of Clayton Kershaw's retirement, explores his complex and legendary legacy, and then pivots to the thrilling chaos of the MLB playoff races with just a week left in the season. The conversation blends personal insights, humor, and baseball philosophy, led by some of the sport’s sharpest minds.

Key Topics & Discussion Points

1. Clayton Kershaw Announces Retirement

[02:57–15:16]

• How the News Broke: Andy McCullough recounts getting word from his colleagues and describes Kershaw’s low-key announcement from Croatia.
• Physical Toll & Family Influence: Kershaw's decision is linked to ongoing physical struggles, especially after shoulder surgery, and pressure/support from his wife and family to have a true farewell at Dodger Stadium.
• A Fitting Goodbye: Kershaw got his sendoff, with fans and teammates saluting him during his final Dodger Stadium appearance.
• Marking the End of an Era: The hosts reflect on Kershaw as a defining figure of the 2010s, alongside Mike Trout, the Giants, and the Astros.
• Comparisons with Scherzer & Verlander: Sam Miller discusses why Kershaw’s return in 2025 was surprising, given how family-centric and understated he is compared to fellow greats Scherzer (“asking Scherzer to quit is like asking a dog to give up the Frisbee” [06:43]) and Verlander.

Notable Quotes

• Andy McCullough:
  “He pushed really hard to get back and have at least one close to full year coming off shoulder surgery…The fans got a chance to, you know, sort of salute him. The team did. And, yeah, it's really just kind of like kind of putting a bow on the 2010s of baseball.”
  [05:25]
• Sam Miller:
  “I just don't really have an explanation for why he pitched this year. And it seems out of character...He doesn't ever seem like he's, like, enjoying himself.”
  [07:16]
• Andy McCullough:
  “He is fairly tortured about the whole thing... He struggles really to give up control. And, you know, missing events with his kids really weighed on him...”
  [09:45]
• Sam Miller:
  “The lesson of Clayton Kershaw is that, you know, no matter how good you get, you're never safe. You're never safe from disaster.”
  [19:19]

Memorable Moment

• Kershaw’s son Charlie now has a locker next to him in the clubhouse—a sign of Kershaw evolving beyond his old all-business persona.
• The roundtable muses on Kershaw's internal struggle, with Andy noting, “He really did enjoy it…just let like the light in and found that he like really did enjoy it, you know…” [10:51]

2. Debating the “Right” Time to Retire (Kershaw’s Perspective)

[15:46–20:49]

• The roundtable debates possible inflection points where Kershaw could have retired, his motivation to keep pitching (“I'm 35. Like, my life's not over. Like, I'm still good at this…” — Kershaw, quoted by Andy [17:47]), and the anxiety athletes feel stepping away.

3. September Races: Reds, Guardians, Tigers & Mets

[21:11–27:43]

• Chaotic Playoff Picture: Contrary to early-season predictions, the last week is filled with drama due to many “mediocre” teams finding themselves on the brink.
• Who’s Even on the Reds?: The roundtable jokes about only learning the Reds’ roster if and when they show up in Milwaukee.
• Meltdowns & Collapses: Lively debate on what constitutes a “choke,” “collapse,” or “meltdown” in baseball. “Choke is like the God tier…a moral component.” — Sam Miller [24:35].
• Mets vs Tigers: Discussion on how the Mets’ and Tigers’ struggles are fundamentally different—one more collapse, the other closer to hubris or a spiraling situation due to inaction.

4. Front Office Philosophy: Windows & Timelines

[27:19–34:37]

• The Tigers’ Big Bet: The hosts speculate that Detroit’s front office may be aiming for 2026–27, not the immediate present, explaining their inactivity at the deadline despite being ahead of schedule.
• Debate on “Windows”: Scott Harris’ belief that “the idea of a window is an illusion” prompts skepticism. Andy counters: “Your window is when you employ Tarik Skubal. That is what it is, man.” [31:32]
• Sam’s Two-Timeline Theory: To succeed, a team must choose between constantly trading now for later or aggressively playing for the moment. “There are only two kind of timelines that really make any sense. One is, there are always teams willing to overpay for now…The other timeline…is like the next four days…When you are in the now and you're not playing for now, you know, that's hubris.” [36:05]
• Process vs. Results: “In America we have a saying and it is scoreboard baby.” — Andy McCullough [33:46].

5. The Joy of the Pennant Race & Cultural Reflections

[37:29–45:43]

• How Much Fun This Week Has Been: The group gets poetic about the electricity of late-September baseball.
• Mariners-Astros Series: Sam shares a broadcast-booth moment that encapsulates September drama; Andy praises the “emphatic kicking” of the Astros in Houston [39:49], and Grant calls Robles’ game-ending catch one of those movie-script moments that make baseball magic [40:22].
• AL & NL Races: Every division and wild card race is still up for grabs, especially in the NL wild card with four teams within a game of each other [41:20].
• “You Have to Be Into It to Be Into It”: Andy and Sam debate why, despite the rise of deep-dive fandoms elsewhere (Marvel, TV, etc.), baseball’s complexity limits its mainstream cultural pull [42:53].
• The Magic—and Challenge—of Baseball: Grant observes that in basketball, you’re guaranteed to see a big play every game, but in baseball, big moments ebb and flow—you need patience and commitment [44:48].

6. End-of-Episode Humor & Callbacks

[45:43–46:31]

• The crew gets lighthearted about past baseball predictions and book sales.
• Grant jokes about confidently proclaiming Javi Baez “back” and sticking to it, no matter what reality says [46:06].
• The hosts close by noting the wild week ahead and promise more chaos on Friday.

Memorable Quotes & Moments

“He is more...fairly tortured about the whole thing...like, he's very open about how much he misses his family. He struggles really to give up control.”
— Andy McCullough on Kershaw’s last years, [09:45]

“The lesson of Clayton Kershaw is that, you know, no matter how good you get, you're never safe. You're never safe from disaster.”
— Sam Miller, reflecting on the meaning of Kershaw’s postseason struggles and their universality, [19:19]

“The best advertisement for baseball is baseball.”
— Andy McCullough, on the sport’s unique rewards and challenges, [42:00]

“There are only two kind of timelines that really make any sense…one is…you can win every trade if you’re trading now for the future…the other timeline…is like the next four days…when you find yourself in that rare position where you’re going into the playoffs, this is the team that you have that’s actually good…that’s a good time to overpay for now.”
— Sam Miller, on team-building philosophy, [36:05]

Timestamps: Key Segments

• [02:57]: Andy recounts breaking news of Kershaw’s retirement from Croatia
• [05:25]: Discussing Kershaw’s legacy and Dodgers farewell
• [06:43]: The “big three” pitchers of the era: Kershaw, Scherzer, Verlander
• [09:45]: Deep dive into Kershaw’s state of mind and struggles
• [19:19]: “The lesson of Kershaw”—what his journey teaches about baseball and life
• [24:28]: Parsing “choke,” “collapse,” “meltdown” as applied to September failures
• [31:32]: Debating team timelines and the illusion of “contention windows”
• [39:49]: Mariners sweep Astros, Mariners’ radio vs. Astros’ TV moment
• [41:20]: Pennant races and wild card chaos across MLB
• [42:00]: Why baseball remains so rewarding—and so demanding—for its fans
• [44:48]: On why it’s hard to sell casual fans on baseball’s patience and payoffs
• [46:06]: Hosts jokingly lock in their old predictions and prepare for the week ahead

Final Thoughts

This roundtable is an essential listen (or read) for anyone invested in baseball’s past, present, and future. It’s part eulogy for an era (through Kershaw), part celebration of the sport’s postseason drama, and part critique of how modern front offices weigh the risk and reward of “playing for now.” The blend of insight, storytelling, and self-aware humor makes The Windup’s roundtable format a must for baseball fans.