The Windup: The Roundtable | Are the Blue Jays winning the offseason?

Podcast: The Windup: A show about Baseball
Hosts: Grant Brisbee, Andy McCullough, Sam Miller
Date: December 15, 2025
Episode: 197

Main Theme

This episode of “The Roundtable” focuses on offseason moves across Major League Baseball, with a spotlight on the Toronto Blue Jays’ acquisition of Tyler Rogers. The hosts analyze the Blue Jays’ offseason strategy, discuss the predictability and logic behind recent free agent contracts, and branch into the Orioles’ headline-grabbing signing of Pete Alonso — examining its implications and Baltimore’s controversial approach to building a roster. They close with reflections on Hall of Fame voting and legacy in baseball.

Key Discussion Points & Insights

Catching Up & Lighthearted Banter (02:23–06:54)

• The hosts open with playful personal updates, discussing facial hair, wedding dancing anxiety, and the elusive benchmarks of adulthood.
• Quote: “I have a belief...that if I could grow a beard, my life would change.” – Andy McCullough (02:56)
• The conversation, though light, sets a candid tone for the episode.

The Blue Jays’ Offseason & Signing of Tyler Rogers (06:57–15:17)

Tyler Rogers: Underrated but Legit (07:27–10:25)

• The hosts highlight Tyler Rogers’ consistently excellent, if unflashy, performance as a reliever.

• Discussion centers around how free agent valuations have become increasingly accurate — with Rogers’ contract being one of the major “misses” this year.

  • Sam Miller: “Tyler Rogers...has the second best ERA in baseball or something crazy...He is not a player who has certain physical attributes that you think maybe you can bring something good out of him. No, no, he's just...good at baseball.” (07:27–09:30)
  • Rogers signed for three years, $37 million — much higher than most outlets predicted (~3:1 value over projections).

• Andy notes Rogers is, “one of the flashier throwing guys there is. He just doesn’t throw hard.” (10:25)

Contract Logic & Reliever Market (10:40–11:47)

• Reliever contracts have become increasingly formulaic (three years, set AAV), suggesting “the market is solved...to an extent” (Andy, 10:44).

• The group agrees: While many Giants fans doubted Rogers due to his unconventional style ("when it doesn't work, it looks like it shouldn't work"), his performance repeatedly proves doubters wrong.

  • Grant Brisbee: “[Rogers’] only fatal flaw...is getting hitters to hit the ball too poorly, too oddly…he can let the other team start a rally by sneezing on the ball…” (11:47–13:12)

The Quirkiness of Rogers’ Results (13:12–15:17)

• Rogers generates odd, “freaky hits” — off the bat handle or nub, barely fair — due to his unique pitching style.
  • “The Babip gods are cruel and fickle, but he’s dealing with the Babip gods dancing drunk at a wedding” (Sam, 13:58)
• The segment concludes with a musing on MLB’s improved contract prediction accuracy, and notes that Rogers’ deal remains an outlier.

Baltimore Orioles, Pete Alonso, and Unorthodox Team Building (15:53–32:34)

Did Baltimore Make the Right Big Swing? (15:53–20:49)

• Discussion pivots to the Orioles’ $155M signing of Pete Alonso, juxtaposed with their ongoing aversion to investing in pitching.

  • Sam Miller: “The Orioles antagonism toward having pitching...doesn’t feel like it’s working.” (17:44)
  • Baltimore’s pitching was 28th in ERA+ last season, despite some metrics suggesting (DRA-) they were closer to average.
  • Their “buy nothing” pitching approach is questioned, but so is the value of offensive overkill absent baseline pitching.

• The group reiterates: “It’s really hard to win consistently if you don’t have average pitching or better,” pointing to league data and historical examples (19:35–20:49).

Pete Alonso: Fit, Cost, and Lineup Impact (22:57–24:55)

• Alonso wasn't the expected big-budget Orioles target, but his consistent power makes their lineup better.

  • “He’s a really, really good hitter. He’s going to make their lineup better. But it is kind of them really leaning in to just not believing in pitchers as a concept.” – Andy (22:57)

• The trade-off between lineup investment and pitching neglect prompts skepticism about the Orioles’ long-term competitiveness.

Hitting vs. Pitching: When Imbalance Fails (26:15–28:07)

• Grant recalls the 1990s Cleveland teams: amazing lineups undone by mediocre pitching. He sees parallels with the Orioles’ current roster.

  • “The idea that you can have generational hitting and not win...that is what the Orioles look like they're setting themselves up for.” (26:41)

• Sam provides nuance: “The problem with the Orioles’ current team-building structure is that on the pitching side you have cascading failure...” (28:07)

  • Punchline: Pitching depth failures are far more damaging than one below-average spot in the lineup.

Market State & Trade Possibilities (32:34–39:19)

• Grant questions if the pitching market is deeper than feared; Andy and Sam push back, saying the supply of true postseason-caliber starters is quite thin.
  • “There are guys who I don't mind giving innings to...but how many pitchers are there that I would give a postseason start to? There are three, four. And that's kind of the line.” (Sam, 37:40)
• The Orioles still have assets to trade for a front-line starter — the question is whether they’ll actually make that move.

Hall of Fame & Legacy: Who Belongs? (40:06–51:03)

The Perennial Hall Debate (40:06–46:49)

• Grant laments not having a Hall of Fame vote during the Jeff Kent years, reflecting on fandom and objectivity.

  • “...He was very good at baseball while I was watching him. Does that mean I can put myself in the context and try and...step back? No, I can’t do that.” (41:14)

• Sam notes the process issues: “It doesn't feel like the veterans committee should be jumping in this quickly...having Kent immediately in feels a little odd...” (42:10)

• All agree that public understanding of Hall of Fame decisions — why certain players like Jeff Kent or Harold Baines get in while others are left out — has gotten harder to explain to the average fan (45:04–45:32).

Bonds, Clemens & Reputation Management (46:49–51:44)

• Conversation shifts to Barry Bonds and Roger Clemens’ continued exclusion from the Hall.
  • Sam wonders, “Why doesn’t [Bonds] try being nice? ...I’m surprised that their only response to this is to privately think, ‘I belong in there, and they suck’...” (48:44)
• Alex Rodriguez’s proactive media persona is contrasted with Bonds’ reclusiveness; hosts doubt that PR alone could change Hall considerations for either.

Nostalgia & Closing Notes (52:22–53:14)

• The episode winds down with a trip down memory lane, discussing obscure teammates and the quirks of former stars’ post-MLB careers.

Notable Quotes

• “Tyler Rogers is...the fourth most repeatable good reliever in baseball history, in my mind.” – Sam Miller (07:59)
• “He just knows how to get outs. He knows how to be good at baseball, and he’s demonstrated it...” – Sam Miller (09:00)
• “His only fatal flaw...is getting hitters to hit the ball too poorly, too oddly.” – Grant Brisbee (11:47)
• “The Babip gods are cruel and fickle, but he’s dealing with the Babip gods dancing drunk at a wedding.” – Sam Miller (13:58)
• “The idea that you can have generational hitting and not win...that is what the Orioles look like they're setting themselves up for.” – Grant Brisbee (26:41)
• “The problem with the Orioles’ current team-building structure is...cascading failure. If you don't have enough pitchers, then you're going to have to fill those innings with even worse pitchers.” – Sam Miller (28:07)
• “[Barry Bonds] is just always sort of been like, you don’t like me, that’s your problem.” – Andy McCullough (52:06)

Timestamps for Key Segments

• Intro & Banter: 02:23–06:54
• Blue Jays/Tyler Rogers Deep Dive: 06:57–15:17
• Orioles, Alonso, Team-Building Philosophy: 15:53–32:34
• Roster Construction and Pitching Market: 32:34–39:19
• Hall of Fame, Legacy, Bonds/Clemens: 40:06–51:44
• Endnotes & Nostalgia: 52:22–53:14

This episode provides insightful, often humorous analysis of MLB’s evolving offseason strategies, player valuation, and the ongoing debate over legacy and the Hall of Fame — all wrapped in the hosts’ signature conversational style.