Good afternoon everyone, it’s time to dive back into the mailbag and answer some of your questions. Remember to send in your questions for our bi-weekly call by e-mail to pinstripealleyblog [at] gmail [dot] com.
MSP Giant asks: What do you see as the liklihood that Yankees pony up for a Skubal-level starting pitcher? Assuming Hal would pay for it, do you think Cashman would give up what it takes to get someone like that? I am guessing Dominguez, Gil or Warren and more.
I think there’s low odds that
they make a move of that level for the immediate future, especially considering Skubal himself would be a pure rental situation akin to the Juan Soto trade where the team would gamble their chances on retaining him for a shot at a title next year. That being said, the window is running out to contend with this core — Aaron Judge will be 34 next season, Gerrit Cole will be 35, and Giancarlo Stanton will be 36. Other players like Carlos Rodón and Max Fried are both under contract for several more years and are in their early 30s already. There’s a solid base of young players contributing to this team that can keep them going in the future, with Ben Rice and Cam Schlittler headlining them currently, but getting the Captain a ring will be a lot harder if they don’t maximize their chances during his prime.
What could Skubal reasonably bring back in a trade this offseason? The immediate reaction from MLB insiders has floated the idea of multiple top 100 prospects, and the Yankees don’t exactly have that on hand at the moment. Still, they have pieces to start a conversation, and anyone not currently contributing to the major league team should be in the discussion if they want to make that gamble. They also have to get off the fence with Jasson Domínguez — if they aren’t starting him full-time next season, in my opinion, they’re wasting his potential. If they’re willing to hear out a move with him involved, they could certainly get in the mix and add an ace to form what would be the most stacked rotation in baseball. Should they go that far? That’s a debate to be had over the next few months, but they got farther than they have in 16 years when they pulled the trigger and added another superstar into the equation. If they have enough ammunition to do it again, they should go for it and figure out where the money goes afterwards.
jmack175 asks: If the knock on Bichette is his defense at SS, what are the odds they could sign him with the idea that he would move to second base after one year when Jazz departs? The free agent SS class for 2027 isn’t huge but much bigger than this offseason.
I don’t think they’re going to move on from Volpe this offseason, so signing Bichette would clutter things up pretty significantly. Bichette and Chisholm are fairly comparable players, but signing a guy who will be looking for top of the class shortstop money with the immediate intention of shifting him to second within a year might not be the wisest investment when you’ve got a player of that caliber here now and can reassess a year later. Volpe has played himself down to what is likely his last chance in pinstripes after his shoulder injury cost him most of his productivity in 2025, but the team is confident enough to give him this run to at least start the year. You can question the logic in that, given that even with his prior years Volpe hasn’t amounted to much with the bat, but hopefully with his defensive prowess back at full health he can be a positive contributor again.
BetweenthePinstripes asks: How does the Jays’ 2025 club differ from the 2024 edition?
This year’s Jays got a lot more multi-dimensional offensively, with Vladimir Guerrero Jr. getting Bichette and George Springer back to high productivity alongside him. Even though Daulton Varsho missed about half the year and Anthony Santander was a net negative on the team, the starting lineup top to bottom didn’t feature any black holes. Their rotation remained solid with Kevin Gausman leading the way alongside an ensemble cast that mostly didn’t rock the boat, including a Max Scherzer that wound back the clock in the latter half of the year and in the playoffs. It probably wasn’t fair to assume the Blue Jays would be as bad as they were record-wise in 2024, given their track record in the last half-decade, but most folks swept them under the rug after seeing the Orioles resurgence, the Yankees’ pennant run, and the Sox going out and trading for an ace. Whether or not they pull off the upset of the Dodgers in the World Series, they’ll remain a thorn in the Yankees’ sides for the foreseeable future.
