The Windup: The Roundtable | How Baseball Has Changed in the Last 10 Years

Episode 193 | November 17, 2025
Hosts: Grant Brisbee, Andy McCullough, Sam Miller
Podcast: The Windup: A Show About Baseball (The Athletic)

Episode Overview

This episode of The Windup Roundtable features Grant Brisbee, Andy McCullough, and Sam Miller diving deep into how Major League Baseball has transformed over the last decade. Using a prompt that Andy posed to executives at the MLB GM Meetings—“What’s something you believed about baseball ten years ago that you no longer believe to be true?”—the trio discusses shifts in pitching and hitting paradigms, the mythology versus reality of "tanking," how organizational development and tech have re-shaped competitive advantage, and more. Along the way, they reminisce about famed agent Scott Boras’s pun-filled press conferences and reflect on changes in baseball writing culture.

Key Discussion Points & Insights

1. Inside the MLB GM Meetings & Scott Boras’s Annual Show

[03:02–11:12]

• Andy recounts his recent trip to the GM meetings in Las Vegas, observing how they’ve changed from intimate, productive gatherings to less accessible, Vegas-flavored events:

  “It just feels more like the winter meetings now. So, I don’t know. I’ll be curious to see how well attended it is in future years.” – Andy McCullough, [06:14]

• The group riffs on Scott Boras’s infamous pun-heavy media performances, with Sam expressing both disdain and fascination:

  “It’s just so poorly executed. The wordplay is as bad as wordplay gets, and now he’s doing alliteration... I’ve said before that alliteration is actually the last refuge of the poor word player.” – Sam Miller, [08:36]

• Andy admits he enjoys Boras’s schtick for the entertainment value, even if the content means little for actual baseball news:

  “I was laughing so hard people were turning around to look at me, and I was confused why other people weren’t laughing. He’s doing… a comedy show.” – Andy McCullough, [10:25]

2. How Has Baseball Actually Changed? Executives’ Answers and the Hosts’ Reflections

[18:13–24:10]

• Andy sets up the main theme by sharing his prompt to MLB executives—what beliefs have fundamentally shifted in the last decade? He asks the hosts for their answers:

  “Is there something you believed about baseball ten years ago that you no longer believe to be true?” – Andy McCullough, [18:28]

a) The Pitcher-Hitter Power Shift & Strikeouts

[19:40–24:10]

• Grant:
  Used to see every swing-and-miss as a hitter failing. Now, it's clear many misses are simply due to impossible-to-hit pitches.

  “There are pitches that a pitcher can execute; you just can’t blame the hitter... If a pitcher can execute that, nothing the hitter can do.” – Grant Brisbee, [19:40]

• Sam:
  Adds nuance about the evolution of how strikeouts are perceived and the hidden virtue of accepting some swings and misses:

  “The benefits you get from allowing swing and miss accrue in other ways... [Luis Arraez] crossed this threshold where all of a sudden he wasn’t striking out enough. Some strikeouts are part of a healthy ecosystem. It’s like bacteria in your gut.” – Sam Miller, [21:36]

• They invoke the “missing a plane” corollary:

  “If you never miss a plane, you’re getting to the airport too early. If you never get caught stealing, you’re not stealing enough. And if you never strike out, you’re not making good swing decisions.” – Sam Miller and Andy McCullough, [22:54]

3. The Rise and Fall of “Tanking” and Organizational Advantage Myths

[24:10–29:09]

• Sam:
  Reflects on the obsession with “the new Moneyball” being tanking around 2015, only to realize now that tanking isn’t the surefire rebuild it was made out to be:

  “It just turns out that tanking’s not that effective. The DePodesta Browns didn’t get good, the 76ers didn’t get good enough... It just doesn’t have a plan to get out of their rebuild.” – Sam Miller, [27:08]

• Andy:
  Explains that what truly separated the Astros and Cubs wasn’t tanking per se, but scouting, international signings, and especially innovation in pitching development:

  “The thing that sustained [the Astros] was their pitching development... The Astros were really the first team that took all of these disparate elements of pitch shaping, Trackman, and all that, and built it at scale.” – Andy McCullough, [29:09]

4. How Competitive Windows, Player Development, and Fortune Intersect

[32:48–37:50]

• Discussion of how success for the Cubs and Astros was as much about luck (drafting the right future stars) as about process. The hosts stress that execution and good fortune can’t always be replicated by “copying” a rebuild:

  “Once they happen, it’s easy to say that happened because of good process, but in the absence of that, it’s not necessarily the absence of good process. It could just be baseball crap that happened to that team.” – Grant Brisbee, [36:32]

5. Diminishing Returns of “Rebuilds” & The Impact of Modern Player Development

[38:52–39:35]

• Teams like the Dodgers and Brewers successfully develop talent without top picks, leveling the field and challenging the old tanking model:

  “Good teams have figured out some of the tech stuff; just acquiring the best players in the draft for three or four years isn’t enough.” – Andy McCullough, [32:48]

6. Baseball’s Cultural Memory and the Challenges of Writing Its History

[39:35–43:29]

• The group debates whether scandals (Astros’ sign stealing) will fade in collective memory and reflect on the changing landscape of sports history and publishing, especially regarding “small window” success stories (e.g., Kansas City Royals).
• Grant shares a darkly comedic anecdote about pitching a baseball history book, only to be told, “No, but seriously, have you thought about a book that would sell?” [43:11]

7. Old Dogmas in Team Building & the Fallacy of the Safe Free Agent

[43:31–47:19]

• Andy:
  Admits a change of heart: he no longer believes in aggressively pursuing “mid-tier” free agents, arguing teams should either sign elite talent or avoid risky multi-year deals:

  “You should really probably only be fishing in the top end of that pool if you’re doing multi-year agreements… Those deals just tend not to work.” – Andy McCullough, [43:31]

• Sam:
  Counters that teams sign solid but unspectacular veterans as insurance, but it rarely produces more security than just going with a rookie or internal option.

Notable Quotes & Memorable Moments

• On the evolution of pitching dominance:

  “If a pitcher can execute [that slider], nothing the hitter could do.” – Grant Brisbee, [19:40]

• On Scott Boras:

  “Watching them die is cringe comedy. And I can’t do cringe comedy.” – Sam Miller, [09:20]

• On tanking:

  “It just turns out that tanking’s not that effective. It’s way less effective than we thought it was.” – Sam Miller, [27:08]

• On the Astros’ real legacy:

  “Their pitching dev isn’t going to be their legacy, but it’s the thing that they did that changed the sport more.” – Andy McCullough, [31:32]

• On failed writing trends:

  “Fake dialogue worked so well and then suddenly it didn’t... there was really something in the collapse of that trend that feels like relevant to like Hypercolor T-shirts.” – Sam Miller, [48:07]

Timestamps for Key Segments

• 01:46–03:15: Hosts check in, Andy recaps his travel ordeal to GM meetings
• 03:02–11:12: GM Meetings’ new vibe; Scott Boras’s annual press conference skits
• 18:13–24:10: Central question: What has fundamentally changed in MLB in a decade?
• 24:10–29:09: Tanking: From market inefficiency to diminished returns
• 32:48–37:50: The fine line between luck, process, and repeating success
• 39:35–43:29: Baseball’s memory, writing history, and the nostalgia gap for teams like the Royals
• 43:31–47:19: Free agent philosophies and the myth of the safe “mid-tier” signing
• 47:19–49:44: The rise and fall of the "fake dialogue" baseball writing trend

Conclusion

“Ten years ago, we had all these truisms… now everything feels so much more context-dependent and complicated.”
The hosts agree: The last decade in baseball has been marked by a shift away from rigid dogmas (“just do Moneyball,” “just tank,” “just lower strikeouts”) towards a new understanding that winning in MLB now demands technological proficiency, player development at all levels, and often just a bit of unpredictable luck.

For listeners:
If you want an insightful but humorous tour of how baseball’s sacred cows have been upended—and what, if anything, remains timeless in team building, fandom, and the writing about both—this is an engaging, idea-rich episode.

Next episode returns after Thanksgiving.