The Windup: The Roundtable | What to Make of the Dylan Cease Deal

Episode 194 — December 1, 2025
Hosts: Grant Brisbee, Andy McCullough, Sam Miller

Episode Overview

This episode of The Windup's Roundtable centers on the blockbuster contract for pitcher Dylan Cease, contextualizing his value and the overall free agent pitching market. Grant, Andy, and Sam dissect not only the specifics of the Cease deal, but touch on larger industry trends, the predictability (or not) of MLB free agency contracts, and what recent market dynamics say about teams’ willingness to spend in the current offseason. The conversation weaves through analytics, the philosophy behind free agent deals, small-market team incentives, and the ever-rising price of pitching.

Key Discussion Points & Insights

1. The Temperature of This Offseason (04:00–06:53)

• Offseason spending is up: Contrary to some expectations, teams are opening their wallets, with the Blue Jays signing Dylan Cease to a seven-year, $210 million deal.
  • Andy: "There’s, there’s money out there to be had and some guys are going to get rich." (04:49)
  • Grant/Andy/Sam's banter touches on the classic bull vs. bear debate, with Andy admitting he’d predicted a slow market, but real conversations with insiders shifted his view.
• Why are teams spending more?
  • Andy: Market opportunities for good-but-not-transcendent players; big spenders like the Dodgers, Mets, Phillies, and Blue Jays can’t sign everyone, so more players are cashing in elsewhere.

2. Is This Free Agent Market Actually "Hot"? (06:53–10:03)

• Contracts lining up with expectations: Despite social media surprise at deals like Josh Naylor’s five years or Cease’s mega-deal, industry predictions (MLB Trade Rumors, Tim Britton) were spot on.
  • Sam: “There was more disagreement going into this offseason about what the market was going to be like than I realized. And so far MLB Trade Rumors was just accurate.” (07:59)
• Formulas, not feelings: Grant expresses amazement at how predictive these models are, while Andy admits to being the type of GM who’d always be outbid by a “more irrational” executive.

3. The Dylan Cease Contract — Rational or Wild? (08:28–15:35)

• Is $210 million for Cease crazy?
  • Andy recounts skepticism given Cease’s 4.5 ERA season and notes that, historically, similar contracts were reserved for perennial aces like Clayton Kershaw.
    • Andy: “It just seems … it’s a lot of moolah.” (09:06)
  • Sam argues inflation is crucial: “We are slow to adjust to inflation … it’s actually just a normal trajectory … baseball salaries, they go up.” (10:03)
• Poker, solvers, and market predictability:
  • Sam compares free agency to computerized (“solver”) poker, saying deals are now almost paint-by-numbers.
    • Sam: “You just like, put the guy in his range and then … that tells you what to do. Dylan Cease contract.” (11:08)
  • Andy adds, “When you're trying to predict some of these contracts, there is a sort of plug and play aspect to it, but … the market will react correctly.”
• Irrationality in the Market:
  • Sam and Andy discuss how the days of teams blowing away the market for a favorite player might be less common, as most organizations have similar evaluations.

4. Dylan Cease as a Pitcher — Perceived Value vs. Reality (20:11–29:58)

• Cease’s “weird” statistical profile:
  • Sam: “If anybody should be polarizing, it should be Dylan Cease … two absolutely phenomenal years in the last five and then he's kind of been whatever in the other three.” (20:11)
  • His high strikeout rate, high walk rate, and good FIP make him look better by some analytics than his traditional stats would suggest.
• Will another team unlock his potential?
  • Andy throws water on the idea other teams will “fix” Cease, noting that the Padres and White Sox are competent orgs and he’s basically who he is.
• Durability as value:
  • Andy: “The biggest argument for Dylan Cease is this guy has taken the baseball, you know, 32 times or more in, like, five straight years.”
  • Sam: “He's bad at [suppressing hard contact], and he makes up for it by striking out a ton of guys … The sum of that is a pretty good pitcher … Clearly sub-ace.” (23:53)
• Comparisons and context:
  • The group discusses historical comps (Blake Snell, Tim Wakefield, R.A. Dickey) but note Cease is valued for dependability more than ace upside.

5. The Blue Jays’ Team-Building Philosophy (29:02–30:40)

• Cease fits a pattern:
  • Toronto values reliably healthy pitchers who post 30+ starts; Cease is another Chris Bassitt or José Berríos type.
    • Sam: “He fits with José Berríos in that sort of way too.” (30:19)
  • The Blue Jays will pay for stability, not just upside.

6. Small Market Teams, Revenue Sharing, and Market Gamesmanship (32:14–40:59)

• Pirates/Marlins free agency posturing:
  • Sam introduces a theory that small-market teams making noise about spending could be for CBA politics—showing “good faith” so they can keep collecting revenue-sharing.
    • Sam: “Revenue sharing is basically a bribe to the Pirates and the Marlins to not be good.” (34:16)
    • Sam: “If the Marlins and Pirates had to be good to make money, they would go sign the players that the Dodgers want. If they don’t have to be good to make money, they'll hang out, take the checks... That feels like a pretty good deal.” (35:12)
• Do big-market teams really want small-market teams to spend?
  • The panel debates if the “rich” teams secretly prefer their competitors to take the money and stay bad, using the Pittsburgh Pirates and Miami Marlins as examples.
• “Bribery” vs. “Perverse incentive”:
  • Andy and Grant carefully clarify no actual bribery occurs—just the legal oddities of MLB’s financial incentives. (37:11)
• Genuine reasons for smaller teams’ interest in spending:
  • Both the Pirates (Paul Skenes, Mitch Keller, upcoming prospects) and Marlins have reasons to try to win now.
  • Sam: “The Pirates have this window with Paul Skenes … and the Marlins have a team that, you know, kind of overperformed, is young, had some really good vibes last year, and has some easily identifiable holes.” (39:10)

7. Why Don’t More Teams Take the Big Risk? (44:08–45:51)

• “Jayson Werth contract” fallacy:
  • Andy put a pin in the long-running annual tradition of outsiders suggesting that bad teams can kickstart a successful cycle with one big free agent.
    • Andy: “It happened one time. It sort of worked. It’s not going to happen again.” (44:24)
• GM incentives vs. team incentives:
  • Discussion about how a GM’s personal desire for job security can sometimes be at odds with the long arc of a franchise.
  • Sam: “If I were advising the Pirates, I probably would not advise them to sign any players. … If I were advising Ben Charrington, I would say sign every player you can.” (44:31)
  • Andy: Many GMs, once fired, regret “wavering from the course,” even if those deviations were small at the time (46:10).
• Poker analogy for front office risks:
  • Grant draws a comparison between a GM’s minor deviations and a poker player missing a slightly larger river bet—probably not fatal, but feels big to the player (47:28).

Notable Quotes & Memorable Moments

• On Market Inflation:
  • Sam Miller (10:03): “We are slow to adjust to inflation. We all have in our mind, like, what a pack of gum costs… but it's actually just a normal trajectory that has been going on for 7,000 years of human commerce. And baseball salaries, they go up.”
• On Free Agent Rationality:
  • Andy McCullough (08:28): “If I was the GM, I would be the guy in the Andrew Fried[man] quote making a rational offer and finishing third on every free agent.”
• On Cease’s Value:
  • Michael Baumann via Sam Miller (25:34): “Cease is both the best bat-missing starter in the majors and the least injury prone starter in the majors. Aren’t those the two most important attributes for a pitcher?... Cease is the worst case scenario for a pitcher who's the best in the world at the two most important things a pitcher needs to do.”
  • Andy: “That is brutal, but accurate.” (25:57)
• On “Stuff” vs. Repertoire:
  • Grant Brisbee (26:17): “Stuff’s cool. Can he prevent runs? Like, that's what we're actually trying to do. We're not trying to impress the East German judge…”
• On Small-Market Team Incentives:
  • Sam Miller (34:16): “Revenue sharing is basically a bribe to the Pirates and the Marlins to not be good.”
• On Blue Jays’ Philosophy:
  • Sam Miller (29:02): “While we're talking about whether Dylan Cease is or is not Superman, they're like, check out Clark Kent over here. That's what we needed. We needed a guy who'll show up in glasses every day. And he is that.”

Segment Timestamps

• [02:05] — Banter & personal updates
• [03:57] — Setting the scene: Hot stove temperature, early spending trends
• [04:09–05:41] — Teams’ willingness to spend in the current climate
• [06:53–08:28] — Snap reactions to Naylor and Cease contracts vs. predictive models
• [08:28–10:03] — Debating if the Cease deal is rational
• [10:03–12:41] — The effect of inflation and market cycles
• [12:41–16:57] — Poker, solvers, and the disappearance of outlier bids in the free agent market
• [20:11–25:33] — What kind of pitcher is Dylan Cease really?
• [25:34–29:58] — Does Cease’s profile fit what winning teams value?
• [29:02–30:40] — Blue Jays’ blueprint for their rotation
• [32:14–42:59] — Pirates, Marlins, and the realpolitik of revenue sharing
• [44:08–47:28] — The problems with chasing the big “Werth” signing; GMs’ personal incentives
• [47:28–48:40] — Poker analogies for front office decision making; episode close

Conclusion

This episode offers an incisive look at the evolving logic of baseball free agency, focusing on why the Dylan Cease deal makes sense in 2025’s financial and competitive context. The hosts conclude that while some deals may appear outrageous using old benchmarks, the market is becoming both more predictable to industry insiders and more rationalized, with even “outlier” contracts fitting into an updated logic. At the same time, small-market teams still face perverse incentives not always aligned with actual competitiveness, and even GMs are not immune from thinking about their own job security first.

If you want to understand how smart baseball insiders view free agency trends, this discussion is as close to an executive roundtable as you’ll get without a Winter Meetings credential.