Not The Weekly Mailbag: Post-Wild Card Thoughts

By Andy Singer

October 2nd, 2026

We had plenty of questions to run a normal SSTN Mailbag this week. However, given the recent Wild Card win and the impending ALDS series against the Rays, I wanted to write about some topics pertinent to the playoffs that didn't necessarily fit with the questions received over the last week, nor did it fit into my game recap from Game 2 of the Wild Card series against the Red Sox. Please, keep sending your questions to SSTNReadermail@gmail.com; questions from this week and future questions will be answered in a future Mailbag.

I also have an apology to make to our longtime reader and commenter, Alan B. Alan asked a question in last week's Mailbag, and somehow I completely missed the topic and question. A long week and late night reading comprehension got the better of me, so I'll catch it next time.

Without any further ado, let's talk about the Yankees and the playoffs:

• One of the the things I want to highlight about the Yankees' decisions in the Wild Card round was their roster construction. In discussing the Yankees' likely lineup and pitching configurations for the Wild Card round, I thought there was some possibility that they'd go with 11 pitchers, but I thought that the Yankees would ultimately get matchup happy and select 12 pitchers, giving them a short bench. It never occurred to me that the Yankees would finally be bold and only place 10 pitchers in the bullpen. The Yankees had a deep bench that allowed them to matchup with whatever pitching combination the Red Sox threw at them. With Schlittler and Fried going, it wasn't likely that the Yanks would have to cover a significant number of innings in each game. If a game went to extras, they had Rodon and Warren stretched out and ready to go. It was a genuinely brilliant decision that I think other teams will emulate in the future.

• Speaking of Will Warren, I know he gave up a gopher ball, but his stuff looked absolutely sick out of the bullpen. He touched 96 MPH with ease, and all of his pitches looked significantly sharper with the extra tick or two of velocity. I had noted the extra velocity when he entered out of the bullpen earlier this season, and the trend has stuck with each subsequent relief outing. Warren looks aggressive out of the bullpen, and he looks good enough that I can't shake the feeling that maybe relieving is a better role for him. That's a conversation for another day, but I think he's a weapon in that role for the Yankees in October.

• Many Yankee fans were at least disappointed that the Yankees didn't snag Adley Rutschman at the Trade Deadline this year. Rutschman has star power and a big name, and the Orioles cashed in by extracting an exorbitant return from the Red Sox. We also know that the Yankees remained in the conversation up to the day of the trade. The whispers at the time were that the Orioles wanted 2 controllable pitchers and big pieces from the Yankees to complete the deal. Jon Heyman now reports that the Orioles asked the Yankees for Austin Wells, Elmer Rodriguez, Yostin Pena (an outfield prospect shooting up prospect boards), and one of Ryan Weathers or Will Warren. If that's true, that would have been an awful trade. More to the point, Austin Wells, for all the early season struggles and media battering he's taken, has been better than Adley Rutschman for the entire 2nd half of the season and was significantly better than Rutschman in a head-to-head matchup in the playoffs this year. For all the early season struggles, I wasn't ready to give up on Wells, and he's validating those feelings. Yankee pitchers have been fantastic all season and are stepping up even more in the postseason, and Wells deserves some credit for that performance as well. Add in his timely hitting at the bottom of the lineup, and Wells is a huge key to the Yankees' success. Sometimes, the best trades are the ones you don't make, no matter how big the name coming to town might be.

• It is beyond obvious that Sonny Gray was cheating on Wednesday night. MLB needs to punish Gray, and likely should punish the Red Sox as well. I'm also shocked the umpires didn't catch it, since even before the broadcast showed Gray's neck, it was obvious he kept touching his neck before touching the rosin on his hat.

• The Yankees have done it at their best this season, but the playoffs proved that they are capable of scoring runs in multiple ways. They hit homers, bunted effectively, stole bases, shortened swings with the infield in, and hit deep fly balls with runners at 3rd base. They also effectively worked counts, something that waned as the season wore on this year. That's what this Yankee offense can be at its best. It needs to keep it going against the Rays, who won't give the Yanks any freebies.

• Aaron Boone out-managed Chad Tracy. For everything negative I've ever written about Aaron Boone, I needed to reiterate that point. I hope he out-manages Kevin Cash as well, which will be a much taller order.

• Back to roster construction. I think, based on how the off-days line up, the Yankees could squeeze by with a 10-pitcher roster again in the ALDS. Warren will remain in the bullpen, and if Weathers is ready to throw 20-30 pitches, he can replace Yarbrough as the lefty out of the bullpen (and unlike Yarbrough or Hill, Weathers can be trusted to pitch against righties). If they do that, Judge can be added to the roster in lieu of Amed Rosario. If the Yanks add a pitcher and Judge needs to be added to the roster, you lose 2 position players. That creates some really tough choices. I think the roster fits better if the Yankees carry 10 pitchers. Everyone is well-rested, and can remain so with the off-day between games 1 and 2.

• Would the Yankees be willing to bring Judge back as a pinch hitter? I really wonder, because you know that Judge will push to play full games at DH or the outfield. I wouldn't want to take either Rice or Garcia out of the lineup against right-handed pitching. This is a delicate situation. I'm fascinated to see how the Yankees handle it.

• If the Yankees get past the Rays, I think they have a very good shot at reaching the World Series. I'm not counting chickens, but I think the Rays will be their toughest test in the AL.

• How good is this Yankees' rotation?!?!? Statistically, it is one of the best in the history of baseball. Securing a World Series win would ensure that it is remembered long after 2026.

• A lot of us felt a little down on the young core in the middle of the season. Now, even national writers are writing about the Yankees having one of the best young cores in all of baseball. It's amazing the difference a couple of months makes, huh?

• I love George Lombard Jr. He is proving that he can rise to the occasion. He reminds me a ton of a young A-Rod in Seattle with the way he plays the game.

• Spencer Jones has been great. He has a huge hole in his swing at the top of the zone that teams haven't exploited enough. I expect the Rays to challenge him with high fastballs. I hope Jones can make the adjustment.

• Trent Grisham remains awful in CF. He let a critical fly ball drop and got lazy getting to it after the bounce, allowing a runner to reach 2nd base in game 2 against the Red Sox. They didn't make him pay, but the Rays will. I worry about playing Grisham in the field.

• As good as the Rays have been, I still feel like the Yankees have the better roster.

• Let's go Yankees!