The Windup: The Roundtable | BONUS – Jane Leavy Talks About Her New Book "Make Me Commissioner"
Original Air Date: September 9, 2025 | Host: Andy McCullough | Guest: Jane Leavy
Episode Overview
This special bonus episode features acclaimed baseball writer Jane Leavy discussing her provocative new book, Make Me Commissioner: I Know What's Wrong with Baseball and How to Fix It. Host Andy McCullough leads a lively, candid conversation exploring Leavy’s diagnoses of the sport's ailments—ranging from the loss of star power to analytics overload—and her ideas for restoring baseball’s vibrancy. The episode is rich with anecdotes, industry analysis, and passionate debate on the tensions between tradition, innovation, and entertainment.
Key Discussion Points & Insights
1. Jane and Her Book: Context and Inspiration
[01:08–08:15]
- Jane sets the tone with characteristic humor, referencing her dog (who plays a recurring mascot role in her work), and swiftly moves to the Yankees’ endless pursuit of roster optimization.
- The impetus for her book: After writing biographies of Koufax, Mantle, and Ruth, she observed the absence of true, promotable baseball superstars today:
“They have no stars anymore. They don’t know how to promote them...they don’t know how to keep them healthy.” [08:15, Jane Leavy]
- The book emerged as a manifesto against what she sees as the sport's “unraveling tapestry”—a direct response to diminished narratives, overreliance on analytics, and disconnect from its past glories.
2. The Star Power Void and Problems Promoting the Game
[08:15–12:49]
- Leavy laments the inaccessibility of today’s stars compared to previous eras.
"It's not like the old days where you could actually get to know a human being..." [08:15, Jane Leavy]
- She notes that Ohtani is exceptional, but even his global reach is commodified by the Dodgers.
- The conversation turns to the alarming scale of pitching injuries and the systemic issues in player health and game narrative:
“There are now 50 new [Tommy John surgeries]...just in the first seven months of 2025. It’s stunning… They’re ripping the fabric of the game apart...” [09:50–11:10, Jane Leavy]
3. Analytics, Entertainment, and Existential Baseball Tensions
[12:49–19:52]
- Andy raises Bill James’s core dilemma: the drive for competitive advantage via analytics versus declining entertainment value.
"...relentless pressure on players and managers to find competitive advantages on one side versus a complete lack of action by management, ownership, and league officials..." [12:49, summary of Bill James’s quote]
- Leavy critiques not only the application of analytics, but the loss of unpredictability and spectacle:
“Analytics don’t tell stories...they’ve really lost that.” [11:40, Jane Leavy]
- Discussion of “cheap” home runs and how power hitting has diluted the drama of the game.
"Do you look up every time there's a home run now? I don't." [15:04, Jane Leavy]
- Leavy proposes a radical solution for more action:
"Put an 18 foot fence around the outfield wall...make it glass so when a ball bounces off, you get more doubles and triples." [16:31, Jane Leavy]
4. The Decline of Fundamentals and the Showcase Culture
[21:40–25:52]
- Rising error rates and lack of fundamentals are pinned partly on youth showcase circuits and fantasy sports, which incentivize individual stats over team play.
- Joe Torrey’s and Dan Okrent’s influence is explored, questioning whether rotisserie leagues began the decline of defense/fundamentals.
"I can't help but wonder whether that was the beginning of the end for fundamentals." [25:03, Jane Leavy]
5. The Search for Intangibles: Can You Measure Grit?
[27:35–29:03]
- Leavy discusses conversations with MIT's Peko Hosoi about the current push to quantify “grit” and intangibles—are we headed for a surveillance state in sport?
"How do you measure grit? One way is to use your eyes, as Dusty Baker said." [27:55, Jane Leavy]
6. Analytics’ Limitations and Baseball’s Human Element
[30:08–32:55]
- Leavy warns of the dangerous overextension of analytics:
"They have so limited the texture of the game, so fundamentally altered it, there's no room for the improbable anymore..." [30:08, Jane Leavy]
- She invokes Peko Hosoi again:
"The people who are running the way life is in America...don’t have domain knowledge...and they don’t think it's important." [31:40, relayed by Jane Leavy]
- Baseball as the canary in the coal mine: what is lost when “the human element” is supplanted by algorithms.
7. The Joy of Imagination and Iconic Plays
[33:34–39:45]
- Example of Rich Hill being benched because "the Astros hit curveballs well," missing the variance and craft of individual players.
- Leavy recounts Derek Jeter’s legendary “the Flip” in 2001, a play that could not have happened in the heavily pre-positioned, analytics-driven shift era:
"...the success of that play was based on...he knew his body, he knew the trajectory of the ball...he could not have seen that if analytics had him...in the shift." [36:34, Jane Leavy]
8. Rule Changes and The Ghost Runner Debate
[39:45–43:20]
- The 2023 rule changes (pitch clock, shift ban, bigger bases) forced Leavy to “start over” her reporting—an overhaul that both improved the game but required new scrutiny.
- She is adamant about the “Ghost Runner” rule’s inhumanity:
“The Ghost Runner is an abomination on humankind… You had to earn it...” [41:38, Jane Leavy]
- Proposal: allow real extra innings for a few more frames before implementing gimmicks.
9. Realignment & Tradition vs. Efficiency
[45:05–45:59]
- Leavy is wary of erasing the leagues’ historical structures for “conference” play proposals.
10. Career Reflections: On Writing Books vs. Daily Journalism
[47:03–48:44]
- Candid advice for would-be book authors:
"Prepare to be suicidal...There's something about writing an 800 word short story seven times a week...If you write four stinkers, well, you got three more chances to make it good..." [47:03, Jane Leavy]
- The loneliness and challenge of long-form, and the pain of losing sacred institutional knowledge among the game’s veteran storytellers.
11. Pitching Armageddon: The Dodgers’ Gambit & Broader Implications
[49:52–52:51]
- A look at the Dodgers’ “injury arbitrage” for acquiring pitchers:
“Their theory is that every pitcher is going to get hurt. So let's acquire pitchers who are already hurt.” [50:14, Andy McCullough]
- Tom Glavine’s theory: Management’s current usage patterns keep down the cost of starters.
12. The Loss of Narrative and Fan Connection
[52:51–56:27]
- Leavy waxes poetic on what’s lost for fans and for the game when unpredictability and narrative are stifled by efficiency regimes.
“Baseball’s essence was that it created narratives...something you can pass down...” [53:09, Jane Leavy]
- The rarity of perfect games, iconic moments, and fan stories in the new era.
- The Kershaw “perfect game” controversy: When precaution denies greatness and reduces reasons for fans to show up:
“By diminishing or deleting even opportunities for greatness, you also diminish...the appeal of the game and therefore, fan base.” [56:27, Jane Leavy]
Notable Quotes & Memorable Moments
-
On the Modern Game’s Malaise:
“They’re ripping the fabric of the game apart... You can’t have rivalries if people can’t stay healthy, you—who are you going to root for when the guy you want to see pitch can’t go to the mound?”
– Jane Leavy [10:35] -
On the Overuse of Analytics:
“Analytics don’t tell stories the way human beings do.”
– Jane Leavy [11:40] -
On Outfield Fences:
“Put an 18 foot fence around the outfield wall...make it glass so when a ball bounces off, you get more doubles and triples.”
– Jane Leavy [16:31] -
On the Ghost Runner:
“The Ghost Runner is an abomination on humankind...you had to earn it. Giving those advantages, rather than teaching people how to play in those situations, has become routine.”
– Jane Leavy [41:38] -
On the Two-Edged Sword of Analytics:
“It's not that they're not smart...But they have so limited the texture of the game...there's no room for the improbable anymore.”
– Jane Leavy [30:08] -
On Writing Books:
“Prepare to be suicidal... If you write four stinkers, well, you got three more chances to make it good...but you don't really have that chance anymore, and certainly not when you're doing a long project.”
– Jane Leavy [47:03]
Important Timestamps
- [01:08] – Episode welcome/intros
- [03:07] – Book release and Yankees discussion
- [08:15] – Decline of baseball’s star power
- [12:49] – The analytics-vs-entertainment dilemma (Bill James quote)
- [16:31] – Leavy’s “crazy” idea: 18-foot outfield walls
- [25:03] – Is rotisserie/fantasy the beginning of the decline in fundamentals?
- [30:08] – The texture of the game lost to analytics
- [36:34] – “The Flip”: Jeter and the lost art of improvisation
- [41:38] – Ghost Runner debate
- [47:03] – On transitioning from daily journalism to books
- [53:09] – Baseball as narrative, not just stats
- [56:27] – On opportunities for greatness and fan engagement
Episode Summary & Takeaways
Jane Leavy’s appearance is a passionate, thoughtful tour through baseball’s contemporary crossroads: balancing the science of winning and the soul of the game. Her central thesis is clear—the pursuit of marginal competitive gains via analytics has come at a steep narrative, human, and entertainment cost. The game’s unique texture—heroes, story arcs, and memorable moments—are threatened when the improbable is engineered out.
With candor and humor, she urges the sport to rekindle its joy, unpredictability, and connection to its past—lest baseball lose what made it America’s pastime.
Jane Leavy’s "Make Me Commissioner: I Know What's Wrong with Baseball and How to Fix It" is out September 9th.