About the Off-Season: “Which Way Do We Go, George?”

About the Off-Season: “Which Way Do We Go, George?” 

By Tim Kabel

January 16, 2026

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The other day, the Yankees finally made a major move and acquired someone who was not on their roster in 2025.  They traded with the Marlins for Ryan Weathers.  He is expected to bolster the starting rotation, which at the beginning of the season should consist of Max Fried, Will Warren, Cam Schlitter, Luis Gil, and Weathers. At some point early in the season, Gerrit Cole and Carlos Rodon are expected to return to the rotation. That will give the Yankees a surplus of pitching. The question is what will they do with it?

There is some speculation that the Yankees may not be out of the running as far as acquiring Freddy Peralta. He is an excellent pitcher, but the problem is that he would be a one-year rental.

The Yankees have done that a couple of times recently. First, they did it two years ago with Juan Soto and now it appears they may have done the same thing with Cody Bellinger. The good thing about the Bellinger trade is that he really didn't cost much in prospects.

There is another option. I read an article yesterday that said that the Minnesota Twins pulled Joe Ryan from the roster of their fan fest, which is set to begin on January 23rd. Now, there could be a lot of reasons why they pulled Joe Ryan. Maybe he will be washing his hair. Maybe he can't find a dog sitter. Honestly, there might be something to the fact that the Twins canceled his appearance. Right now, the Twins don't have many players whom the fans would be excited to see. Ryan is one of their best and most popular players, so it is a little suspicious that he won't be at the fan fest. Perhaps, that's because they don't expect him to be on the team by the end of January. Ryan was rumored to be on the trading block last summer. Ultimately, he was not traded, but if he is prior to the 2026 season, he would bring back a hefty return.

Clearly, this is just speculation but if the Yankees were able to swing a deal for Ryan, he would be a huge upgrade to the rotation. Imagine when all the dust settles by mid-season, the Yankees could have a starting rotation of Gerrit Cole, Max Fried, Joe Ryan, Carlos Rodon, and Cam Schlittler. If you assume that either Will Warren or Luis Gil was included in the trade for Ryan, the other one could be part of the bullpen. I don't know if the Twins are actually going to trade Ryan. However, it seems like a distinct possibility. I also don't know if the Yankees are interested in acquiring him. Ryan will not be a free agent until 2028, so the cost would be higher. The Yankees may feel that acquiring Weathers was enough to complete the renovation of their starting rotation.

Again, this is just speculation, but it is a direction the Yankees could go. They do have other needs besides pitching, such as a right-handed bat and an upgrade in the infield. Cody Bellinger remains a possibility but that is seemingly less likely than it was. The Yankees have been linked to Bo Bichette, who could play second base or third base for the Yankees moving forward. It is unclear what they will do with Jazz Chisholm, Jr.. Will they keep him through the 2026 season and let him become a free agent? Will they sign him to an extension? Will they trade him now? 

There are many different paths the Yankees could take over the next few weeks. They didn't do much of anything up until this week. They were stagnant and hibernating throughout most of the offseason. There is only about a month before Spring Training starts. So, whatever moves the Yankees are going to make need to be completed very soon.

I suspect the trade for Ryan Weathers was the first domino to fall. That may lead to other trades and free agent signings. If Brian Cashman wants to build a team capable of winning the World Series, he has moves to make. Could acquiring Joe Ryan be one of those moves? Yes, it certainly could. 

That's the most interesting aspect the Yankees’ offseason at this point. They could go in almost any direction. Here's hoping that they pick the correct one.