The Windup: The Roundtable | Last Day of the Regular Season Madness & Ranking the Wild Card Matchups

Hosts: Grant Brisbee, Andy McCullough, Sam Miller
Date: September 29, 2025
Episode Number: 180

Main Theme & Purpose

This episode of The Windup’s Roundtable dives into the chaos and drama of MLB’s final day of the 2025 regular season (Game 162), with an in-depth analysis of the playoff landscape and the wild card matchups. Grant, Andy, and Sam unpack the emotional swings of the regular season finale, debate current playoff structures and tiebreaker rules, and break down each upcoming Wild Card series with characteristic wit and inside-baseball insight. They finish with World Series predictions and a candid assessment of the teams least and most likely to make a run.

Key Discussion Points & Insights

Reflections on "Game 162" and the Demise of Tiebreaker Games

[02:01]

• Sam Miller laments the loss of tiebreaker games and suggests a more chaotic alternative:

  “Imagine…after the last out of the season, they open the envelope and decide what the tiebreakers are, then Sunday would have been more tense."

• Grant agrees with Sam’s desire for chaos, adding how it would improve finales:

  “I love your idea. I feel like it’s more chaos, but in a helpful way...it should have been the whole Sunday to me."

• The group debates the impact on teams like the Guardians and Tigers, noting the drama that was lost with predetermined tiebreakers.

Emotional Stakes: Marlins’ Motivation and Broadcast Perspectives

[05:16]

• Andy brings up how the Marlins’ investment in spoiling the Mets’ season was seen as “salty” by some media, but views it as a culture win:

  “For me, the fact that the Marlins cared about this series is such…a resounding victory for them as an organization..." (06:01)

• Sam confesses to initially sneering at the Marlins’ exuberance, then recognizes its authenticity and value:

  “The tendency to judge people for caring is not a good tendency. It's not one that…humans should lean into. And so great, the Marlins brought it.” (09:09)

• They reflect on the contrasting vibes between the "checked out" Mets and the scrappy, invested Marlins, highlighting how effort and culture matter beyond standings.

The Mets’ Offseason Dilemma & Steve Cohen’s Spending Paradox

[13:22]

• Andy questions why Mets owner Steve Cohen, with virtually unlimited resources, is hesitant to outbid for elite starting pitching:

  “Should Steve Cohen have just said, ‘No, I’m not going to stop. I'm Steve Cohen, I’ll give him a billion dollars if I have to.’” (14:17)

• Sam explains the philosophical tension:

  “What actually restricts Steve Cohen from spending more is an interesting one...the difference between 350 million and 650 million is nothing to him.” (16:42)

• Andy:

  "I've...the theory that I've had for years and years is like, it's genuinely hard to create a $300 million payroll because you have to do things that so many people in the organization will be like, what are we doing? This is a terrible allocation of resources." (17:39)

• The segment delves into baseball's internal constraints, the influence of “smart deal” orthodoxy, ownership “club” pressures, and why even a mega-wealthy owner self-limits.

Wild Card Series Rankings, Previews & Analysis

[29:39 & 30:11]

Interest Rankings

• Andy’s Interest Order:
  1. Red Sox vs. Yankees (“Classic series. Two good teams. …the favorite in the American League.”) (30:11)
  2. Padres vs. Cubs (“Classic exciting series. …some famous players. ...athletic. ...nice uniforms.”)
  3. Dodgers vs. Reds (“Should be what it is, but who knows.”)
  4. Guardians vs. Tigers (“God bless them all.”)

Detailed Series Previews

• Red Sox-Yankees:

  • “There is a little bit more juice to Red Sox, Yankees now. ...It feels less forced and…it feels like these two teams weren’t necessarily direct competition…looking forward to this series because they’re both very flawed teams. But…they’re both pennant worthy.” - Grant (31:45)
  • “I don’t feel [Red Sox-Yankees fatigue] anymore. …That’s a good matchup.” - Sam (31:45)
  • “The Yankees offense is extraordinary… bullpen was so bad [but] they had to get a whole bunch of extra relievers. …They’ve got a lot of firepower.” – Sam (32:15)

• Dodgers-Reds:

  • Caution urged before assuming Dodgers will steamroll Reds.
    “The concept of scoring points will be a very big challenge for [the Reds], especially with the Dodgers rotation.” – Andy (39:29)
  • Concern for Dodgers: bullpen is a “wreck,” and their rotation’s command is sometimes shaky (Yamamoto, Snell). Reds have dangerous starting pitching. (41:00)
  • “There’s always the possibility the Reds just show up and find that the wrong Dodger team walked off the bus.” – Sam (41:46)

• Padres-Cubs:

  • “The Cubs used to be the one you felt sorry for. Now, not so much. The Padres…at some point, it’s like, okay, that was funny. Now just come on, give Preller the prize. …But…Padres losing, too, because it’s…an interesting story on its own.” – Grant (44:55)
  • Andy is most looking forward to Padres-Cubs for its chaos and fun, tipping San Diego “but who the heck knows.” (45:26)

• Guardians-Tigers:

  • Consensus least interesting match-up (“God bless them all”). But also running theme on the Guardians’ ugly-but-inspiring path:

  “The Guardians...296 on base percentage...is the lowest by a playoff team ever. ...The median team with a .296 on base percentage lost 100 games. The Guardians won 11 more games than any team with [one] that bad.” – Sam (50:49)

Broader Playoff Structure & Fairness

[42:02]

• Andy and Sam agree that the three-game wild card series can produce unfair outcomes, but accept it as part of the tournament:

  “I don’t need it to be fair at all. It’s a tournament. …You can make it chaotic." – Sam (42:32)

• The hosts see the all-home-field advantage as a suitable compromise.

World Series Predictions

[45:29 & 46:23]

• Andy: “I think Dodgers over Yankees is my World Series pick.” (45:58)
• Sam: “Mariners in the AL … probably Phillies in the NL. Mariners win it.” (46:23)
• Grant: “Phillies, Red Sox. Heart says Mariners, Padres.” (47:12)
• The hosts call out “office pool” randomness and acknowledge that most playoff predictions are for fun.

Blue Jays, Brewers, and Other Contenders

[48:25]

• They admit being less bullish on the Blue Jays despite the best AL record, lumping them with the Brewers as “really good regular season teams” but less trustworthy in October.

Notable Quotes & Memorable Moments

• On Tiebreakers:

  “If playing for a tie was still…tense…imagine…after the last out of the season, they open the envelope and…decide what the tiebreakers are.” — Sam Miller [02:05]

• On Marlins’ Grit:

  “The point is to get up, put your pants on, and care about something.” — Andy McCullough [07:05]

  “The tendency to judge people for caring is not a good tendency. It's not one that…I think humans should lean into. And so, great, the Marlins brought it.” — Sam Miller [09:09]

• On Mets & Spending:

  “What actually restricts Steve Cohen from spending more is an interesting one…what is it that makes him not just say…I have spare billions and this is the thing I care most about in my life?” — Sam Miller [16:42]

  “It’s genuinely hard to create a $300 million payroll because you have to do things that so many people in the organization will be like, what are we doing? This is a terrible allocation of resources.” — Andy McCullough [17:39]

• On the Guardians:

  “The Guardians .296 on-base percentage…is the lowest by a playoff team ever…The median team with [that] lost 100 games.” — Sam Miller [50:49]

  “Guards ball, baby. It’s not a bug. It’s a feature.” — Grant Brisbee [50:55]

Timestamps for Important Segments

• Intro & Episode Opening: [01:42]
• Game 162 & Tiebreakers Discussion: [01:49] – [04:52]
• Marlins, Mets & Broadcast Banter: [05:16] – [13:05]
• Mets Offseason, Cohen, & Big Spending: [13:18] – [27:29]
• Wild Card Series Rankings & Previews Begin: [29:39]
• Red Sox-Yankees Preview: [31:45]
• Dodgers-Reds Discussion: [37:44]
• Reds Pitching Analysis: [43:10]
• Padres-Cubs Preview: [44:55]
• World Series Predictions: [45:29]
• Blue Jays as Afterthought: [48:25]
• Guardians’ Odd Historic Offense: [50:01]

Tone & Style

The conversation maintains a candid, playful, and slightly irreverent tone throughout—a blend of sharp analytics, deep baseball knowledge, banter, and running inside jokes. The panel is critical, but not mean-spirited, and regularly acknowledges absurdity, unpredictability, and the joy of baseball chaos. The language is peppered with wit and self-deprecation, making for an engaging listen (or read) even if your favorite team didn’t make the playoffs.

Summary

This episode is an essential end-of-season listen for MLB fans who want to understand the underlying drama of Game 162, gain insight on playoff team identities, and enjoy a smart, entertaining breakdown of wild card narratives. Whether you’re a chaos-loving baseball fan or a playoff structure purist, The Windup’s Roundtable provides both perspectives—with plenty of laughs and honesty.