About The Off-Day: Ready Or Not, Here It Comes

About The Off-Day: Ready Or Not, Here It Comes

By Tim Kabel

September 18, 2026

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The Yankees have ten games left in the regular season. Tonight, they begin their last road series of the regular season with a three-game set in Arizona. Then after a day off on Monday, they will play four games, including a doubleheader on September 22nd, against the Tampa Bay Rays. Finally, they will wrap up the season next weekend at home against the Orioles. As I wrote this, the Rays won their game against Oakland. Therefore, the Yankees will go into the series against Arizona trailing the first-place Rays by 5 games.

Even if the Yankees were to sweep the Rays in those four games, which is unlikely, they will still probably be in second place. The most likely scenario is that the Yankees will be the top Wild Card team and will host a best of three-game series against the Red Sox. The Yankees currently lead the Red Sox by six games in the standings. Because the Yankees won their season series against the Red Sox, the Red Sox would need to be a full game ahead of the Yankees to be the top Wild Card team. That is virtually impossible.

Aaron Judge left the game on Wednesday against Minnesota with a leg injury. He reportedly spent most of yesterday undergoing treatment. At this point, it is still unknown how severe the injury is. It is safe to assume that it will probably cost Judge a minimum of two or three games. That is an absolute best-case scenario. There haven't been many best-case scenarios involving the Yankees or Judge lately. Judge played six games since returning from the IL and was struggling to get his timing and swing back. That is completely natural and expected. That's why he was playing the games. The point was to get him ready for the playoffs. If this injury keeps him out for any of the remaining regular season games, that will potentially derail his rehabilitation. If it is anything longer than that and keeps him out of the actual playoff games, the Yankees will be in a lot of trouble.

The Yankees could win the series against the Red Sox because they will have Cam Schlittler starting game one. However, without Judge, the Yankees offense is somewhat questionable. There are some questions regarding players other than Judge. Will Trent Grisham be ready? Will Jazz Chisolm, junior be ready? How effective will they be after missing time? In the case of Grisham, there are other issues. He wasn't very effective before he went on the IL. Would it make sense to keep Spencer Jones in the starting lineup? Would Aaron Boone do that? The same scenario can be presented regarding Jazz Chisolm. At this point, would the Yankees be better off keeping Anthony Volpe at second base? Would Aaron Boone do that?

Another issue is the fact that Gerrit Cole has struggled lately, particularly in giving up home runs. Again, he is recovering from Tommy John surgery that cost him all of 2025. This is natural, normal, and to be expected. However, it is still a problem. Max Fried has missed a lot of time due to injuries and is building himself back up. In his career, he has struggled in the postseason. Will he be effective? The most likely starting rotation for the Yankees in the playoffs against the Red Sox would be Cam Schlittler, Max Fried, and Gerrit Cole, most likely in that order. It is conceivable that Aaron Boone would put Cole in Game 2.

It is very easy to imagine a match up in game one of Cam Schlittler against Payton Tolle. Cam Schlittler is the better pitcher. He is most likely going to be the American League Cy Young Award winner this season. He deserves that honor. However, he is unlikely to pitch nine innings. It is easy to picture a scenario in which Aaron Boone brings in Brent Headrick, Tim Hill, or Paul Blackburn. While they have all been solid this season, they have struggled

recently due to their excessive use. Headrick has essentially appeared in half of the Yankees games this season. Depending on how much these pitchers are used in the remaining ten games in the regular season, that overuse could come back to bite the Yankees. 

Clarke Schmidt appeared in his first Major League game in 14 months on Wednesday. He pitched 2/3 of an inning. To thrust him into a major role in the playoffs might be foolish. The same would apply to Ryan Weathers if he is even able to return by the time the playoffs begin. If you're thinking that Aaron Boone would never do such a thing, just remember Nestor Cortes in the World Series against the Dodgers in 2024.

In a best of three-game series against the Red Sox, the Yankees can Ill afford any managerial mistakes. Those tend to happen with the Yankees, particularly in the postseason. If for example, Boone pushes Jazz Chisholm and Trent Grisham into the lineup over Anthony Volpe and Spencer Jones, that could be a major mistake. Both Chisholm and Grisham had underwhelming seasons, to put it nicely. Grisham was in the middle of a slump when he injured himself. It is unlikely that after a layoff of a few weeks, he will return as a modern-day version of Rod Carew. He won't. However, we have seen this before. Boone favors veterans over younger players. Even if the veteran is washed up or faded. It doesn't matter to Boone.

The decision of whether to play Chisholm or Volpe will be a bit of a conundrum for Boone, as he favors both players.  If it were my decision, I would start Volpe, particularly against Payton Tolle.

The Yankees are on the cusp of entering the playoffs. They're not exactly at their best. Unfortunately, there is nothing that can be done about that. They are going to have to try to advance with what they have. There is a lot of uncertainty here and we may not have all the answers until the playoffs actually start.

Heck, we might not have all the answers until the playoffs are over.