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Yankees Mailbag: Figuring out the offseason plan

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Check out the answers to this week’s mailbag.

National League Wild Card Game 2: Cincinnati Reds v. Atlanta Braves Photo by Adam Hagy/MLB Photos via Getty Images

Good afternoon everyone, it’s time for this year’s final round of mailbag questions. Remember to send in your questions for our weekly call by e-mail to pinstripealleyblog [at] gmail [dot] com.

Chuck asks: The longer this drags waiting to resolve LeMahieu’s contract the higher the risk of losing out on getting pitching. At what point does Cashman move on and what is the next step?

So we’ve heard a lot about LeMahieu being the focus point of the Yankees’ offseason, but it’s not like they aren’t monitoring the rest of the free agent market. They haven’t been reported as serious suitors for any particular pitcher, but that is more of a fault to their overall plan rather than a byproduct of chasing LeMahieu into the winter. Perhaps they just aren’t too fond of the guys available as free agents, or maybe they feel that the trade market is simply a better alternative to improving the rotation. If it’s the latter, it would make more sense as to why we haven’t heard too much leak about who they’re targeting.

Jason B asks: What would the Yankees have to offer the Reds to get Luis Castillo?

Speaking of trades, this would be one to consider for sure. Josh wrote a piece earlier in the week breaking down why Castillo would be a valuable addition to the team, and I have expressed in previous mailbags that I think Castillo would be an ideal addition for the Yankees. That being said, any trade for a pitcher of Castillo’s caliber is going to hurt in prospect cost, and as Josh mentioned that means being open to dealing Jasson Dominguez.

It’s not that the Yankees don’t have the prospect pool to send over some equivalent value to the Reds, if they wanted to empty the farm for a top-end pitcher they very well could. The problem comes in that teams want quality, not quantity when they trade for non-MLB ready players, and other prospective trade partners have had better top prospects that they’ve been willing to offer whenever the Yankees have attempted improving their rotation this way. Dominguez may just be the best prospect the team has had in decades, but he’s yet to even play in rookie-league ball yet. Dominguez is years away at best, and the Yankees have their core built up for contention right now. It’s not an easy decision to make, but it’s something they have to consider.

Ruff Trade asks: Do you think the Yanks, meaning Hal/Cash, have a clear idea of what they’re doing this year? I’m not being facetious. I know their goal is to field a playoff contending team and let the crapshoot take hold, but as we’ve seen, this approach is pretty crap and always exposes their weaknesses. Is there any chance that they have a vision here or is just consistently getting under the luxury tax most years the goal?

And with no one really knowing what the next CBA will look like, shouldn’t they assume the thresholds will be somewhat if not significantly higher in the future?

I’m not thrilled by it either, but I do think this is the goal they have in mind. The Yankees are easily a playoff-caliber team, especially if we’re looking at some form of expanded playoffs in the near future. An extra round probably only reinforces this organizational philosophy, since it makes the randomness of the playoffs increase even further. Prioritizing marginal upgrades at the cost of their bottom line isn’t going to fly with Hal, if there’s a short enough window where going above the luxury tax is viable — like when the team signed Gerrit Cole — they’ll go for it but eventually they’ll work their way below it.

Now, I think this is foolish for a franchise that prints money, but my opinion is hardly going to sway Hal or the business people around him. As far as the CBA talks go, I’m not too optimistic on that either. The player’s union isn’t what it used to be decades ago, and they’ve been on the losing end in more recent iterations of these negotiations. The owners already treat the luxury tax like a quasi-hard cap, and it’s not impossible to imagine a world where they lobby for an actual hard cap going forward.