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“This time, the Cubs cannot get cute.” “So, about that lineup …” Well, the Cubs answered in a definitive way: They signed Alex Bregman (and the Red Sox did not). Does this make Chicago contenders? Plus: Tarik Skubal’s unprecedented arbitration case, and is baseball angling for an in-season tournament? I’m Levi Weaver, here with Ken Rosenthal — welcome to The Windup!
Big Swing: Bregman to the Cubs
We all knew it was time for the Cubs to address the lineup. On Saturday night, they corrected last year’s mistake, signing third baseman Alex Bregman to a five-year deal worth $175 million (an AAV of $35 million).
It has me wondering: Are these last two moves — Bregman and Edward Cabrera — enough to make the Cubs the runaway NL Central favorite? Or is this a set-up for the fourth consecutive installation of everyone’s favorite game, “Just Kidding: It’s The Brewers Again!”
I did a little thought exercise. Going position by position, I plugged in the new guys, comparing them to who they’ll be replacing from last year’s squad:
- 3B: Matt Shaw (3.1 bWAR) —> Alex Bregman (3.5 bWAR)
- SP: Michael Soroka (-0.1) —> Edward Cabrera (2.8)
- RP: Drew Pomeranz (0.9) —> Jacob Webb (0.3)
- RP: Brad Keller (1.4) —> Phil Maton (1.3)
- RP: Taylor Rogers (0.4) —> Hoby Milner (-0.6)
- RP: Andrew Kittredge (0.6) —> Hunter Harvey (0.7)
- Backup 1B/UTIL: Justin Turner (-0.1) —> Tyler Austin (estimated 0.6)
There are many flaws with this, of course — bWAR isn’t the best stat for evaluating relievers, and park factors should count for something. Also we’re just sorta best-guesstimating a bWAR for Tyler Austin, since he spent the last five years playing in Japan. So take it all with a fist-sized grain of salt.
But for an estimate: This puts them at +1.8 bWAR. Not bad?
My biggest flaw is that it’s not really Shaw-for-Bregman straight up, is it? Shaw is still on the roster. You know who isn’t? Kyle Tucker (4.6 bWAR in 2025). Swap him in for Shaw on this list, and the Cubs are suddenly at a net +0.3 bWAR.
But hey, you could also argue that Cabrera’s arrival replaces two pitchers. Soroka was likely to be gone anyway, so adding Cabrera to the rotation also pushes Colin Rea back into rotation depth.
By spring, there will be loads of more well-rounded projections, factoring in things like: How will Justin Steele look when he returns from UCL surgery? Will Moisés Ballesteros and Kevin Alcántara be major contributors? Will “Clark the Cub” ever fully recover?
But projections aren’t likely to account for Bregman’s much-lauded intangibles. Nor will they factor in the Midas-like witch’s curse that rewards every Brewers trade of yet another star with more division championships.
I have no idea if the Cubs will be great. But they’re better than they were last week. Now: hold on to Nico Hoerner?
Ken’s Notebook: Breaking down the Skubal-Tigers rift
Here’s Ken Rosenthal, from his latest column:
The most fascinating thing about the Tarik Skubal arbitration case is that both sides think the other is trying to break established norms.
Skubal’s team, the Tigers, believes his ask for $32 million is far beyond what the system historically has dictated. Skubal and his agent, Scott Boras, believe the Tigers’ $19 million filing number does not account for two rarely cited provisions in the CBA that set him apart.
By meeting both provisions — the first as a player with special accomplishments, the second as one with five or more years of service — Skubal need not compare himself only to pitchers in his class. He is permitted to argue the relevance of all players’ salaries, including those who negotiated lucrative contracts in free agency.
The expected hearing in February will take place against the backdrop of Skubal’s uncertain future in Detroit. The Tigers, coming off back-to-back playoff appearances, spent the offseason upgrading their roster. But they also left the door open for trading Skubal, arguably the best pitcher in the game. And now that they’re picking a fight with him in arbitration, it seems more unlikely than ever they will make an aggressive bid to retain him in free agency.
The three independent arbitrators MLB and the Players Association jointly select to decide cases are notoriously unpredictable, making Skubal’s outcome anyone’s guess. But Skubal is the perfect player to test the boundaries of the system. If he remains healthy and effective in 2026, his final season of club control, he might receive $400 million in free agency. So if the panel awards him $19 million instead of $32 million — a big raise from his $10.15 million salary last season instead of a massive one — he will not exactly suffer.
It’s certainly fair to question the Tigers for not filing a higher number, but portraying this battle as one between team and player would be an oversimplification. MLB’s Labor Relations Department recommends salaries for teams to offer players in arbitration. The PA advises player agents on how to best represent clients. In some ways, the Skubal case is but a preliminary to the main event — the heavyweight bout looming between the league and union in collective-bargaining negotiations.
More: A Tigers-Tarik Skubal arbitration hearing would be fascinating theater. Cody Stavenhagen tells us why.
Replacement Recs: Where does Boston go from here?
Bregman was No. 3 on our Free Agent Big Board. How do the Red Sox replace a guy like that?
Well, they don’t. Not from a clubhouse/leadership standpoint. But there’s still a way to improve their lineup: sign the No. 2 guy on that list. Bo Bichette is not only four years younger than Bregman, he’s also a better hitter. Let’s compare last year’s stats:
Bregman vs. Bichette
| PLAYER | AVERAGE | OPS | HR | bWAR | fWAR |
|---|---|---|---|---|---|
|
Alex Bregman |
.273 |
.821 |
18 |
3.5 |
3.5 |
|
Bo Bichette |
.311 |
.840 |
18 |
3.5 |
3.8 |
Other than bWAR, this chart does not take into account Bregman’s Gold Glove defense at third base, or the fact that Bichette would have to adjust to a new position at second base (assuming Trevor Story stays healthy, which … 🤞). But he would be a big boost to the lineup.
The thing is, Boston is not the only potential suitor for Bichette. He’s meeting with the Phillies today, and a Toronto restaurant offered him free steak for life to stay put.
Jen McCaffrey has more on the mindset that led Boston to let Bregman walk (and the idea that Bichette should be the next primary target) here. She also notes that if he goes elsewhere, there are other options (including Eugenio Suárez and Isaac Paredes) for Boston.
Hmm … Could we see an MLB in-season tournament?
Rob Manfred, during his time as commissioner, has overseen a lot of changes, many of them rules-based: the shift ban, the pitch clock and — coming soon to a ballpark near you — the Automated Ball-Strike System.
Manfred spoke this week to WFAN, and had a lot to say about other changes he’s considering before retiring (which he insists he is definitely doing) in January 2029.
The first, which has been talked about for much of Manfred’s tenure, was expansion and realignment. Nothing really new there, except he said he would prefer to keep the two-team cities in different divisions.
Next: a free-agency deadline. His assertion is that it would attract more attention to the sport during the offseason. The MLBPA vehemently disagrees, saying it would lead to contract suppression.
But the topic I found the most … let’s say, “intriguing” … was the idea of a split season and/or a in-season tournament, like the NBA Cup.
As someone who has been on board with all the other changes I mentioned above, I feel qualified to say: I hate it. Not for any special or creative reasons, either. Just for the same ones others are bringing up: It could lead to a reduction of regular-season games, or it could push the World Series into Thanksgiving territory.
There are, of course, reasons to argue in favor of it: There’s the money. There’s also the cash, the moolah, the profits, the increased revenue and let’s not forget: the dough.
(Cupping hands to mouth) Boooooooooooooo …
But hey, maybe you disagree. Chad Jennings, Andy McCullough and Sam Blum tell us about the pros and cons — and why baseball is different from basketball — here.
Handshakes and High Fives
All nine teams remaining on Main Street Sports/FanDuel network (formerly Diamond/Bally Sports) have cancelled their contracts. Evan Drellich gives us the teams’ remaining list of options.
It looks like we can put this one to rest: The Diamondbacks are not planning on trading Ketel Marte.
In a little over a week, we’ll know who’s joining Jeff Kent in the Hall of Fame Class of 2026. Tyler Kepner says Chase Utley’s arc is an indication of an evolution in voting.
Most-clicked in our last newsletter: The Last Dive Bar getting ahead of the Oakland Sacramento Las Vegas Athletics on selling trademarked merch.
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