The Windup: The Roundtable | Ohtani is really good at baseball, what's next for the Brewers & Game 7!

Podcast: The Windup: A show about Baseball
Host: The Athletic (Grant Brisbee, Andy McCullough, Sam Miller, Bill Simmons)
Episode: #186 (October 20, 2025)

Episode Overview

This lively episode of The Windup's Roundtable centers on Shohei Ohtani’s latest historic performance, what comes next for the perennially fascinating Milwaukee Brewers, and the tension of an imminent ALCS Game 7. The panel (Grant Brisbee, Andy McCullough, Sam Miller, and Bill Simmons) bring their trademark humor and candor, riffing on feats of baseball greatness, organizational philosophies, postseason heartbreak, and the psychological toll of championship droughts.

Key Discussion Points & Insights

1. Shohei Ohtani’s “Greatest Day” and His Unique Place in Baseball

Timestamps: 03:04–14:53

• The hosts dive straight into Ohtani’s latest historic playoff game, with Grant jokingly asking if he just had the “greatest day of any person who ever lived, ever.”
  • Quote [03:04, Grant Brisbee]: "Did he have the greatest day of any person who ever lived, ever in history, sports or not? That's where we're at. The hyperbole has. No, but I mean, you. You saw the articles. Like, did he have the greatest baseball day ever?"
• They discuss Ohtani’s three-homer, six-shutout-inning night in the clincher, noting its singularity:
  • Sam and Bill compare Ohtani to Rick Wise’s two-homer no-hitter (which was obscure until recently), noting how Ohtani’s feats truly stand alone.
    • Quote [05:59, Bill Simmons]: "Ohtani is... you can't put him in hand-to-hand combat with other ballplayers. It's just not... they're doing different movies."
• Panelists marvel at Ohtani’s dramatic flair and the near-mythic quality to his heroics:
  • Andy describes him as "one of one," a refrain adopted by the Dodgers and echoed—at first as awe, then as overused cliché.
  • The “Marvel superhero” analogies fly thick, cementing Ohtani’s otherworldliness compared to baseball peers.
    • Quote [07:04, Grant Brisby]: "He's Galactus. He's eating worlds."
    • Quote [07:37, Grant Brisby]: "It's almost like when it works out that neatly, it's like, okay, come on."
  • Discussion turns to the tantalizing sense that Ohtani can rise to dramatic moments on cue, defying expectations at every turn.
    • Quote [08:57, Andy McCullough]: "He does, though, I think more than any player I can remember, have a sense for, like, dramatic tension and sort of narrative arcs..."

2. Ohtani’s Ambition: What’s Next? Cy Young Focus?

Timestamps: 12:00–18:28

• Examining the future, the panel speculates about Ohtani's next frontier.
  • Bill suggests Ohtani may attempt to prioritize pitching achievements, especially chasing a Cy Young Award.
    • Quote [12:00, Bill Simmons]: "Shohei Ohtani is the only one who's in a flying race, you know, and he's setting records in flying. If everybody could fly, they also would be worse than him at flying."
  • Andy asserts Ohtani’s inner drive is still motivated most by pitching. Predicts his goal for next season is to win the Cy Young.
    • Quote [13:44, Andy McCullough]: "I would suspect that his goal for next season is to win the Cy Young Award."
• They discuss the challenges for Ohtani to win a Cy Young as a two-way player (volume, rest days, etc.), noting he often excels in rate stats but falls short on innings compared to full-time pitchers.

3. The Brewers’ Philosophical Crossroads: Regular-Season Success vs. Postseason Ceiling

Timestamps: 18:28–35:44

• Turning to the Milwaukee Brewers’ postseason ouster, the crew ponders the lessons and the future for the franchise.
  • Questioning whether their offensive one-run-in-four-games output signifies structural problems or mere postseason randomness.
    • Quote [19:05, Bill Simmons]: "It's a generation-long trend kind of at this point, so you can't totally ignore it..."
  • Both Bill and Andy point out the youth and potential of the Brewers’ position player core (names like Bryce Turang, Sal Frelick, William Contreras, Jackson Chourio), emphasizing sustainability.
  • Grant and Bill debate whether the Brewers’ lack of a true superstar is a fatal flaw when it comes to World Series hopes.
    • Quote [31:07, Bill Simmons]: "It just feels like the Brewers don't have anybody that you would really say that about right now, and I don't know how much that matters. I have gotten in my head... that stars win in the postseason."

Philosophy of Team Construction in a Small Market

• The table weighs "run it back"—maintaining their current core and occasionally trading from strength (e.g., Freddie Peralta) for the next set of prospects—vs. pushing payroll or trading for more star power.
  • Grant advocates for Milwaukee "going for it" this offseason, perhaps emulating teams with higher payrolls (Diamondbacks, Orioles).
    • Quote [28:51, Grant Brisby]: "I would think this is the off season where they would just say, you know what, let's, let's get a blank... this would be the off season to spend rather than do the same old same old with Freddie Peralta."
  • The others are skeptical, citing market limitations and philosophical commitment to consistency and regular season excellence.

4. Game 7 Preview: Mariners vs. Blue Jays and the Weight of Droughts

Timestamps: 37:45–49:43

• The hosts set the stage for a winner-take-all ALCS Game 7.
  • The Blue Jays’ current form and Vladimir Guerrero Jr.’s hot streak inspire some confidence.
  • Mariners' rotation looks “gassed,” and panelists wonder if, in a Game 7, plans just go out the window.
    • Quote [38:46, Bill Simmons]: "They had a plan. That plan was rock solid starting rotation and it's just not working. They're kind of like, they've got guys who look gassed right now."
• Grant and Bill discuss how home-field advantage sometimes matters less than expected—sometimes fan anxiety after long championship droughts can become self-fulfilling (references to Mariners, Blue Jays, Maple Leafs, Giants).
  • Quote [41:06, Grant Brisby]: "Sometimes that's what happens in baseball... when the first thing goes wrong... 42,000 people thinking, you know, for the last 30 years I feel like I've seen things gone wrong for this team..."
• A fun debate follows: How long without a championship is enough to consider a fan base truly “cursed,” with Andy and Bill riffing on what the right level of sports fatalism is for Blue Jays and other long-suffering fan bases.

Notable Quotes & Memorable Moments

• [07:04, Grant Brisby]: "He's Galactus. He's eating worlds."
• [08:57, Andy McCullough]: "He does, though, I think more than any player I can remember, have a sense for, like, dramatic tension and sort of narrative arcs..."
• [12:00, Bill Simmons]: "Shohei Ohtani is the only one who's in a flying race, you know, and he's setting records in flying."
• [13:44, Andy McCullough]: "I would suspect that his goal for next season is to win the Cy Young Award."
• [19:05, Bill Simmons]: "It's a generation-long trend kind of at this point, so you can't totally ignore it..."
• [31:07, Bill Simmons]: "It just feels like the Brewers don't have anybody that you would really say that about right now, and I don't know how much that matters. I have gotten in my head... that stars win in the postseason."
• [41:06, Grant Brisby]: "Sometimes that's what happens in baseball... when the first thing goes wrong... 42,000 people thinking, you know, for the last 30 years I feel like I've seen things gone wrong for this team..."
• [45:04, Grant Brisby]: "They've also watched people wait for the Maple Leafs to win a Stanley Cup and then those people have died. And so like that's in their head too where it's like whatever has to happen, happen."
• [46:27, Andy McCullough]: "I just think that in general, being a sports fan is about a lack of fulfillment if you're only searching for a championship."

Timestamps for Key Segments

| Segment | Start | End | |--------------------------------------------------|----------|----------| | Introduction, Ohtani as "One of One" | 03:04 | 10:48 | | Ohtani’s Next Step: Pitcher Futurism, Cy Young? | 12:00 | 18:28 | | Brewers’ Postseason Woes and Roster Discussion | 18:28 | 35:44 | | Brewers’ Model, Payroll & Trade Philosophy | 25:23 | 35:44 | | Game 7 Preview, Fan Anxiety, "Cursed" Franchises | 37:45 | 49:43 |

Final Thoughts

This episode is essential listening for anyone invested in baseball’s present and future—whether marveling at Ohtani’s unprecedented stardom, questioning what makes a franchise successful long-term, or feeling the agonies and ecstasies of rooting for a championship-starved team. The hosts blend sharp analysis, playful banter, and the occasional existential musing, making for an episode as entertaining as it is insightful.