About The Off-Season: I’m Thinking...

About The Off-Season: I’m Thinking...

By Tim Kabel

November 5, 2026

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The Yankees have quite a few needs going into the 2027 season. They need a right-handed hitting catcher to either complement Austin Wells or replace him. They need a third baseman. They need some relief pitchers. They may or may not need a second baseman, depending on how they view Anthony Volpe.

We are going to hear a lot of rumors about what the Yankees may or may not do. We are also going to read a lot of articles by experts suggesting what the Yankees need to do. Because of the possibility of a lockout beginning at midnight on December 1st, it is quite likely that the Yankees may make moves earlier than they have in seasons past. Some of the free agents on the market are saying that they want their contracts with new teams in place before December 1st. 

Well, when you add all those things together, you get the article I read the other day. It said that Tarik Skubal, who has stated that he wants to be signed with his new team before December 1st, is a target of the Yankees. Well, to be to be precise, the article stated that the Yankees have said they are “thinking about signing Tarik Skubal.” That statement makes a few things pop into my head.

First, why would the Yankees be interested in signing Tarik Skubal when starting pitching is their biggest strength? They have a starting rotation of Cam Schlittler, Gerrit Cole, Max Fried, Carlos Rodon, and either Will Warren or Ryan Weathers. At this point, they also have Clarke Schmidt as a possibility. Even Elmer Rodriguez could fill a role. In a way, signing Skubal wouldn't make too much sense for the Yankees. That's where it gets interesting. The article stated that because there really are not a lot of great position players available in free agency this year, the Yankees might instead sign Skubal and then trade some of their surplus starting pitching to get a position player they really wanted.

That idea actually makes a great deal of sense. If the Yankees signed Skubal, they would then have a starting rotation of Schlittler, Skubal, Cole, and Fried in the top four spots. They could then trade either Rodon, Warren, or possibly Weathers to acquire a position player such as CJ Abrams or another young top star. The only position player to whom I have seen the Yankees connected in free agency is Teruaki Sato, the third baseman from Japan. The point is that although signing Skubal would not address a direct need for the Yankees, it would address other needs indirectly. It does make sense. It would also give the Yankees the best starting rotation in the Major Leagues.

Another thought that popped into my head was that this seems familiar. The Yankee seem to think about doing a lot of things. I can easily imagine Brian Cashman and Hal Steinbrenner sitting on a porch somewhere with their sleeves rolled up, sipping some lemonade and perhaps munching on ginger snaps while pondering possible moves for the Yankees. They would start out early in the morning, before the sun got too hot. They would keep going all day long, just thinking. In the afternoon, as the sun went high in the sky, they would use handkerchiefs to mop their brows. Occasionally they might speak but mostly, they would think. When dusk fell, they would still be there, thinking. Other teams might actually make some moves, acquire players, pull off a trade, sign a free agent. Not our Yankees; they are thinkers. 

The point is that in the past, the Yankees have thought about doing a lot of things but really haven't done much. When the player they were supposedly thinking about signing actually signed with another team, Brian Cashman usually said, “well, we were thinking about it but we never got a chance to pull the trigger.” Or, “we were in on it but the terms we were looking for never materialized.”

Based on that, I don't think the Yankees will ever move past the thinking stage when it comes to Tarik Skubal. You see, all this thinking without actually acting takes a lot of time.  Tarik Skubal has already said that he wants to have everything done early. He does not want to wait past the end of November. He doesn't want to take a chance of there being a lockout which might impact the type of contract he can sign. He wants his money in the bank and his signature on the contract before a lockout could happen. Skubal is not going to sit around and wait while Brian Cashman and Hal Steinbrenner sit on their porch in their rocking chairs, thinking.

Thinking is wonderful. I have been known to do some of it myself. However, thinking should lead to acting. That's the part the Yankees frequently forget. I believe they will forget it once again this off-season.