The Windup: A Show About Baseball

Episode Title: The Roundtable | Winter Meetings Preview
Date: December 5, 2025
Host: Grant Brisbee
Panelists: Andy McCullough, Sam Miller

Overview

This episode centers on a preview of MLB’s upcoming Winter Meetings, while also exploring the evolution of baseball fan/media analysis, free agency trends, and the challenges of balancing old vs. new content. The conversation is equal parts industry meta-analysis and baseball nerdery, with reflections on content creation, the difficulty of assessing player signings, and the cultural mood of baseball fandom.

Key Discussion Points & Insights

1. Modern Content Overload & Nostalgia

Timestamps: 02:08–06:44

• The hosts lament the loss of passive, linear TV experiences from their youth, wishing for a simpler content landscape.
• Sam Miller critiques the relentless churn for new content, saying,

  "Most stuff is age is fine...a few hundred [movies/TV/music] was enough. You could spend your whole life watching those few hundred." (04:08, Sam Miller)

• Discussion of how content creation feeds a demand for constant novelty — for both creators and consumers.

Notable Quote:

"I write a subscription newsletter, and...90% of the stuff I write about is as fresh today as it was the day it came out, which is to say, not fresh at all...[but] two weeks later, nobody will look at it. They want new stuff." (04:36, Sam Miller)

2. The State of Baseball Analysis & Fan Reactions

Timestamps: 10:26–15:14

• The trio pivots to discussing the shifting ground of analyzing MLB free agent signings and trades.
• Andy McCullough reflects on the difficulty of evaluating moves with modern metrics:

  "The analysis for every move became: 'Great, they’re trying,' which, you know, fair, because teams kind of stopped trying in some ways. And now...I think that, like, we as an industry have not totally figured out [a replacement analysis]." (13:02, Andy McCullough)

• They discuss how the broad use of "value per WAR" as a litmus test for deals has faded, with less consensus and clarity in public discourse.

Notable Quote:

"We used to have this, like, simplistic way of going, well, a WAR costs $10 million. If it’s over, your team’s dumb; if it’s under, your team’s smart. I don’t really see that logic anymore." (12:21, Sam Miller)

3. Case Study: Cody Ponce’s Signing & Giants/Knee-Jerk Cynicism

Timestamps: 12:56–23:16

• Panelists dissect public reaction to the Blue Jays signing Cody Ponce, with many Giants fans decrying their "poverty franchise" for being outbid.
• Grant Brisbee explains his less-cynical take:

  "Just because they didn’t pay for this $30M pitcher doesn’t mean that $30 million isn’t out there somewhere for another pitcher...they just didn’t think he was worth this much." (19:47, Grant Brisbee)

• Debates the modern fan’s baseline assumption that their team’s executives are either "idiots" or "too cute by half" (overthinking), rather than acknowledging limited information or complexity.
• The hosts reflect on cycles of trust/distrust between fans and front offices, influenced by previous eras and broader cultural trends.

Notable Quotes:

"It’s funny how the team that finishes second gets all the shame...But 29 teams came to the same conclusion." (23:16, Sam Miller)
"I think we’re in the 'executives are too cute by half' era...The default mode is that these guys are being too smart and not doing the obvious thing." (26:58, Andy McCullough)

4. How Analysts Construct Narratives About Big Signings

Timestamps: 30:09–34:03

• The panel discusses the evolution of analytical approaches:
  • Old method: project WAR, divide by known $/WAR, and declare good/bad deal.
  • Current method: more ambiguous; context, team needs, and league environment weigh heavily.
• Grant Brisbee admits most "big" signings are "good for a while and then...suck," but that’s still worth celebrating.
• Andy McCullough and Sam Miller note that context (team cycle, division, fit) increasingly matters more than numbers-based projections.

Notable Quote:

"The good news is you’re probably going to like this trade today. And the better news is by the time you start disliking this trade, you may well be dead. Because that will be in the future." (32:38, Andy McCullough)

5. Free Agent Market: Has Compensation Become "Solved"?

Timestamps: 38:58–45:11

• Sam Miller shares research suggesting that team predictions for free agent contracts are converging — with annual values now much closer to public predictions than a decade ago.
• This could suggest a hyper-competitive, data-driven environment, or potentially hint at proto-collusion via analytics.
• Andy McCullough counters that technology and available comps naturally drive teams towards similar valuations, making "collusion" hard to prove.

Notable Quotes:

"If in fact, salaries are solved...the downside is if you're a free agent and get seven offers and they're all about the same, that looks a lot like collusion." (43:24, Sam Miller)
"One of the wonders of technology is, you can collude without having to call the other teams...Everyone’s got a version of the same computer." (44:04, Andy McCullough)

6. The Colorado Rockies’ Surprising Front Office Moves

Timestamps: 45:29–49:05

• The Rockies are lauded for hiring “seasoned baseball guys” rather than "hot, young genius" types.
  • Comparisons to "The Expendables" and "Traveling Wilburys" are made for comedic effect.
• This reflects a minor industry trend back toward valuing veteran perspectives — a form of counterprogramming to analytics-focused leadership.

7. Meta-Reflection: Predictive Baseball Analysis is a Losing Game

Timestamps: 37:18–38:58

• Grant thoroughly lambasts the inherent futility of confidently predicting which free agent contracts will "work:"

  "Every team that works up the war-per-dollar and they have all these...and they do it—and it still doesn’t work because that’s just the nature of baseball. No, we’re all stupid. We’re all stupid. And some people are smart." (37:57, Grant Brisbee)

Notable Quote:

"We are the other side of hitters. When they hit .280, they’re failing 72% of the time. Like, that’s us. Except we’re not hitting .280—we’re hitting like a hundred." (37:57, Grant Brisbee)

Highlighted Quotes with Timestamps

• Content/nostalgia:

  "We don’t need to keep redoing [stories]...There’s only seven plots. We don’t need 7 billion applications of it." (04:08, Sam Miller)

• Baseball analysis fatigue:

  "We have all these reactions to this doomed pursuit of trying to gain control by saying, 'Ah, they're stupid. They're smart.' No, we’re all stupid. We’re all stupid. And some people are smart." (37:57, Grant Brisbee)

• Executive critique era:

  "I think we’re in the 'executives are too cute by half' era. The default mode is that these guys are being too smart and not doing the obvious thing." (26:58, Andy McCullough)

• On deal analysis haze:

  "The good news is you’re probably going to like this trade today. And the better news is that by the time you start disliking this trade, you may well be dead, because that will be in the future." (32:38, Andy McCullough)

Useful Segment Timestamps

• Opening cultural digression: TV nostalgia & content creation: 02:08–07:12
• Winter Meetings and market analysis intro: 10:26–15:14
• Public perception of MLB executives/cycles of trust: 21:00–29:08
• How writers approach big signings: 30:09–34:03
• Analytics, “solved” free agent compensation: 38:58–45:11
• Rockies’ front office discussion: 45:29–49:05
• Futility of predictive analysis: 37:18–38:58

Tone & Takeaways

The episode skillfully balances humor, self-deprecation, and industry insight. The hosts are candid about the limitations of modern analysis and the fickleness of both front offices and public opinion. They issue a gentle warning about overconfidence in projections and embrace a realistic, almost existential approach: both teams and writers do their best, but baseball is, at its core, unpredictable and human.

For listeners:
This episode is a perfect mix of meta-baseball nerd talk, insight into front office/franchise decision-making, and a humorous window into how even top analysts get lost in the fog of baseball’s perpetual unpredictability. If you want both hot stove talk and philosophical baseball navel-gazing, it’s a must-listen.