Thoughts a Few Days Before the Winter Meetings

TFW “the dollars will be there.”

The offseason is in full swing now. Well, kind of. A few signings have happened already, of course, but no players have signed with a compensatory draft pick attached yet. That’s when things will really get going. Even still, though, there are actual rumors and I appreciate that. The dog days of the offseason are the worst without them.

Anyway, the Yankees are obviously connected to a lot of these rumors, and I have a lot to say about it. Let’s get right into it.

1 Brian Cashman Goes Cole Mining: The Yankees–meaning Brian Cashman, Aaron Boone, and new pitching coach Matt Blake–flew out to the West Coast yesterday to meet with Gerrit Cole. Now, on the one hand, of course the Yankees are going to meet with Gerrit Cole. It would be malpractice not to, and they always do their due diligence. Given their recent track record with top-shelf free agent pitchers and lack of willingness to commit long-term money, I understand why many fans are skeptical here. Fool me once, etc.

With that said, though, I think that there is a lot of evidence here to suggest that the Yankees are going above and beyond simple due diligence. In fact, I think we could go so far to say that they’re very seriously pursuing Cole and that he is indeed a top priority.

To start, Ken Rosenthal reported that the Yankees are “making him their priority” this winter. Joel Sherman reported that even simply going to visit Cole, as opposed to making him come to New York, is a sign that they’re being much more aggressive than they were last winter with top free agents. And now, just this morning, Jon Heyman said that while there was no money specifically discussed at their meeting yesterday, it was clear that “the dollars would be there.”

It’s easy to be skeptical of this, as I mentioned earlier, but I also think it’s a bit lazy. Last offseason was extremely frustrating and it was indeed part of a larger trend with the team and their spending habits. However, it was also consistently and immediately reported that the Yankees were lukewarm on Corbin, Machado, and Harper. It was also repeated that they had clear financial limitations and would likely not meet the players’ demands.

That suggests that the team itself is not whispering skepticism into reporters’ ears, which is good news. A lot of fans have suggested that this is laying the groundwork to say “we tried” when Cole inevitably signs elsewhere, but I disagree. In fact, I think last year, by saying that they weren’t really in the running, was much more reflective of that approach. None of that has happened this year, but maybe I’m just a glass-half full kinda guy.

This has been said many times, but it does feel reminiscent of CC Sabathia in 2008. The Yankees half-heartedly pursued Johan Santana the previous year but clearly weren’t serious and then clearly signaled to CC Sabathia early on in the process that he was their top priority. That’s exactly how I’m reading these recent news reports about Cole, and I think you should, too.

2. California Bound: I’m already sick of the “Gerrit Cole prefers the West Coast” talking point. Why do people believe this? I haven’t seen it seriously suggested by anyone, and Cole himself denied it. Sure, it makes intuitive sense that a guy wants to play close to where he grew up. I get that. But I chalk this up to be in the same category as “Cole was a Yankee fan growing up.” Who cares? This is a business. There’s more that goes into these conversations and deals than location or childhood fandom. At the end of the day, it will likely come down to money and contract length, and that alone.

If Cole really wants to play out West, then so be it. Cliff Lee didn’t want to play in pinstripes, and neither did Shohei Ohtani. That sucked but was ultimately fine. What are we going to do about it? The players have agency and if they have other priorities, it is what it is. What the Yankees can control is making a serious and legitimate offer for his services and that’s about it. Based on the tenor of the reporting, as I said above, that is what I think is happening. This is encouraging. Vague whispers about his locational preferences shouldn’t even register on your radar until they’re not attributed to “concerns” by teams.

3. Meeting with Strasburg, Too: Rosenthal also reported that the Yankees will be meeting with Strasburg, which is neat. That will likely happen today or tomorrow. That’s good news but feels much more like due diligence to me than Cole does. Strasburg is a hell of a pitcher who would look great in pinstripes, don’t get me wrong. But I don’t get the same sense from the reporting that he’s viewed the same as Cole by the Yankees, and that’s okay. (It’s also right; I think Cole is a superior option for a lot of reasons.)

Maybe that will change if it becomes clear that a marriage between the Yankees and Cole isn’t going to work out, but for now, I’m not reading too much into this. Strasburg really strikes me as a candidate who will most likely stay in Washington, but who knows.

4. The Wheeler of Fortune: Zack Wheeler is about to get paid, huh? He already has a $100 million offer in the hand, which is great for him. There’s obviously quite a bit of untapped potential with Wheeler. Heyman says that the Yankees are “talking to him” but are much more focused on Cole/Strasburg, which is great news. If Wheeler really does have those offers in hand and the Yankees aren’t moved, then that removes another secondary option after the top tier guys.

That they’re letting the Wheeler market play out while going after the big fish is another sign to be encouraged, in my opinion. Wheeler would be a classic “well, we tried, here’s our plan b” option, and that doesn’t seem to be what the Yankees are doing here. Again, I am encouraged by this.

5. And Now, We Wait: Finally, it seems like the Yankees’ offseason won’t really get underway until the Cole/Strasburg markets play out. They are obviously operating on some sort of budget, though we don’t know what it is, and one of those pitchers will command a big chunk of it. Teams have been rewarded, unfortunately, for waiting out the market in recent years. That helps explain why Brett Gardner is not back yet. It also might explain why there hasn’t been a lot of movement with Dellin Betances or Didi Gregorius. Patience has borne fruit of late.

Combine that with the apparent aggression re: Cole, and I think we can see the shape of the offseason unfolding. Hopefully, we continue to get good news about Cole and his sweepstakes wrap up sooner rather than later. I don’t think the market will really unfold for the Yankees until that happens, one way or another. Fingers crossed.


Adam Ottavino’s homecoming [2019 Season Review]


Surveying the market for Didi Gregorius


  1. RetroRob

    Many fans aren’t good at context. Defeatist by nature. It’s clear the Yankees are in on Cole. It makes sense on so many levels, from competitively, brand, and financially. I won’t be annoyed ir he goes to the Angels or the Dodgers by his choice. I will be annoyed if it turns out the Yankees didn’t make the best offer. They will, or they will certainly make it clear they will make the best offer. What happens from there is in Cole’s court.

  2. Re: Gardner. I’m wondering if they might already have a deal in place with him but are waiting until the Spring for the 60 day DL to open up again before they formalize the signing. If they signed him now they would have to waive or trade a prospect. After the 60 day DL opens up they will have 40 man roster space. At the very least Hicks will be on it. Since it’s such a foregone conclusion he will be back (both sides presumably want it), then why not just wait until it is more advantageous to the team to complete the signing? Or perhaps they are just waiting until some space clears up through the inevitable small trades that will be taking place.

  3. I think it’s surprising Wheeler is said to be close to signing at this point. Sounds like he has some pretty good money on the table though. But, he could have a bigger market if he waits for Cole and Strasburg to ink deals right?

    • RetroRob

      Trying to out-wait Boras is tricky…and dangerous. That’s Boras’ game. He no doubt wants Wheeler off the board as it will remove a fall-back option for teams looking at Cole or Strasburg.
      Wheeler waiting longer might have found himself without a job come March. Eventually, teams spend their money and build their rosters. A $118 million deal is not always available come spring. That’s quite a deal for him. I was thinking he’d get in the $80 million range.

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