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.
ReadingYankee asks: Given the injury history of these two pitchers who are potential front line starters, which one has the best possible outcome in the next couple years: Chase Hampton or Bryce Cunningham? Obviously, this would be assuming they do not get injured again.
On the surface it’s a difficult call: MLB’s prospect rankings listed Cunningham above Hampton at the end of last year, but Hampton was listed as much closer to the majors, which is a major factor in determining if pitching prospects are going to pan out or not. However, given Hampton’s two extra years in the minors amounting to just a 71 inning difference in experience between the two, I’d give the edge to Cunningham having the easier path to the majors and thus contributing quicker. Because the truth is, we simply can’t assume that neither one gets injured again during their development — there’s nothing more volatile than a pitching prospect, and this is the risk they run. Cunningham’s first year being disrupted isn’t too much of a surprise, but Hampton’s now tossed just 18.2 innings in the last two years, 5.2 of which came in Double-A, and it’s hard to see a world where he can rise to the majors quickly even if he has a stellar 2026 to turn things around.
Chip23 asks: So, if we take Cashman’s statements at face value, that he has put together a “Champion-caliber roster” then should we also assume that a failure to win a championship is a reflection of the manager and that he will be held accountable?
Not necessarily, because there’s a bit of word-play from Cashman going on whenever the topic of being championship-caliber gets discussed. Because the organization views championships and the postseason at large as being a crapshoot (whether that’s correct or not is a a different discussion, one we’ll talk about in a second!), so long as the team is in the running and plays in October baseball, it’s not a failure to miss out on outright winning a title. If that wasn’t the case, then Cashman and Boone would be in extremely hot water by now having only gone to and lost a single World Series during their tenure — but as we know, the organization is quite comfortable with both of them running the ship. Perhaps things would change if they flamed out in the Wild Card Series a couple years in a row, but even with the relative disappointment of losing convincingly in the ALDS the team can point to the fact that they were tied for the most wins in the division and competed with the team that went to the World Series.
The idiot that said, “Harper is coming” asks: Can we change the terminology from “running it back” to “walking it back”? One implies a little more urgency than the other. I don’t see any urgency from this organization to be worthy of “running it back.”
So, let’s get into the thought process of the offseason overall, shall we? There’s no denial that the team didn’t display much urgency this offseason: they locked in fairly early on bringing back Cody Bellinger without showing much interest in the top of the market with Kyle Tucker, called his bluff when he was adamant about pushing for extra years and were willing to let someone else sign him, and then mostly fixated on minute bullpen moves to flesh out the roster while bringing back bench pieces. However, where they stand at the end of the day is still a top three team by FanGraphs’ projections, and outside of the Dodgers’ horde of talent they’re firmly in the mix to be the second-best team in baseball.
On the one hand, they weren’t pushing to improve themselves very much this offseason, which has it’s frustrations (which I share). On the other, they correctly assessed that they had a top team in 2025 that ran into another top team, and reasoned that they can get back to the Fall Classic with the roster they have now. Is it how I personally wish they operated this winter? No, I wanted them to be much more aggressive, but at the end of the day I’m not upset with the result either. I just wish it could’ve been settled about a month or two ago so we could’ve avoided the endless cycle of questioning whether they’d do something interesting.
OLDY MOLDY asks: Do the Yankees avoid another Boone June Swoon in 2026?
Here’s a case where I’d argue Boone could and should be held accountable for his record — because while the team has gotten into the dance every year barring one, they sure have looked highly inconsistent at the very consistent rate. Their almost penciled-in summer of poor play each year has been one of my major gripes with the team, and it lines up with their level of preparation that got put on display for the world when the Dodgers took them to task in 2024. Their fundamentals have been, in my opinion, highly suspect throughout this championship window, though mainly from 2020 on. Finding a way not to nosedive and potentially cost themselves the division with a terrible two-month stretch would go a long way towards building more faith in what they’ve constructed, so here’s hoping Boone and company can avoid it this year.
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