Once again this season, the Red Sox and the Yankees will face off in a best-of-three series to kick off the playoffs.
The Red Sox weren't expected to be here based on their start to the season, but they've been playing exceptionally well for months. The Yankees, on the other hand, have always been a strong team in the American League.
Last year, the Yankees defeated their rivals while seeded fourth in the American League. Will history repeat itself?
Let's break it down.
The Pitchers
As for the starting pitchers, the Yankees are still deciding. Do they want to give the ball to Cam Schlittler or Max Fried for Game 1?
Logically, Schlittler—who will win the Cy Young in a few weeks—should be the choice. But Fried is a veteran and will be more rested, making him a strong option.
The Yankees also want to monitor Schlittler's workload, which is why they're hesitating. But as far as I'm concerned, they shouldn't overthink it: they should start Schlittler on Tuesday.
If there's a Game 3, Carlos Rodon and Gerrit Cole are options.
For the Red Sox, the path seems clearer. Payton Tolle and Sonny Gray (who hasn't had much success at Yankee Stadium in the past) are expected to pitch on Tuesday and Wednesday.
Ranger Suarez is expected to start on Thursday, if there's a Game 3.
Payton Tolle is getting love from Yankees fans, but knows it's temporary
![]()
310 to Left is brought to you by @neforddealers, the official truck of the Red Sox.
(via MLB on X) pic.twitter.com/SY53qBJc1d— NESN (@NESN) September 25, 2026
In the bullpen, the Yankees don't have many sure things. David Bednar is clearly one of them—he's an excellent closer.
If Brent Headrick and Paul Blackburn still have some gas left in the tank, they'll come in handy.
But the Yankees don't have a dominant bullpen, the kind we've come to expect in the playoffs over the past few years.
John Schreiber, Ryan Yarbrough, Michael Fulmer, and Yerry De Los Santos are ones to watch.
Will any of the starters (Gerrit Cole, Carlos Rodon, Will Warren, Ryan Weathers) make occasional appearances out of the bullpen?
And most importantly, will prospect Carlos Lagrange be called up?
“He had an injury and just started throwing live again. He's not in the mix right now. Could be down the road, but he's not in the mix yet.”
– Aaron Boone on Carlos Lagrange pic.twitter.com/aFYMW2EOm8
— SNY Yankees (@snyyankees) September 25, 2026
In Boston, Aroldis Chapman isn't at 100%. He's a guy who can be a game-changer if he can perform.
Garrett Whitlock, Tyson Guerrero, Erik Miller, Jovani Moran, Brayan Bello, and Greg Weissert are names to watch.
Could Jake Bennett be used out of the bullpen in the Bronx? What about Patrick Sandoval? Potentially, yes.
But the real question is whether Garrett Crochet will be able to pitch in relief. Because that could be a game-changer.
Garrett Crochet won't pitch in a regular-season game; here's why the Red Sox won't rule out a postseason rolehttps://t.co/ub83F5chcV
— Sean McAdam (@Sean_McAdam) September 24, 2026
Position Players
The big question we're asking ourselves just a few days before this series is whether the Yankees' captain will be there. And if so, in what condition?
Aaron Judge, who disagrees with his manager over how to publicly describe his injury, wants to play at all costs.
Aaron Judge expressed displeasure with Aaron Boone for revealing the “moderate” calf strain, saying, “I don't know why he used those words.”
— Bryan Hoch
(@BryanHoch) September 24, 2026
If Judge were to play, it would be a huge help to Ben Rice. Rice has had an excellent season, but he's performed better when he's been protected in the lineup.
Jazz Chisholm Jr., Cody Bellinger, Paul Goldschmidt, Jose Caballero, Luis Garcia, and Spencer Jones are the other names to watch. And… Anthony Volpe, too.
We'll also be watching to see if Giancarlo Stanton and Trent Grisham will be able to return to action.
In Boston, the team is in a similar position to the Yankees, as a key hitter (Willson Contreras) remains a question mark.
Wilyer Abreu, Jarren Duran, Ceddanne Rafaela (who isn't 100%), Caleb Durbin, Roman Anthony, Adley Rutschman, and Trevor Story are players to watch.
The loss of Mickey Gasper, whose season may be over, won't help.
The Managers
Aaron Boone is no stranger to this kind of situation: he knows how to manage his team. I don't expect him to stand out in a negative way.
He knows what he's doing.
Chad Tracy is an excellent manager who just earned a contract extension, but he has less than a year of experience as a major league manager.
How will he handle himself in the Bronx, under the pressure of the playoffs?
The Unpredictables
A series between these two great rivals always draws attention. It will undoubtedly be the most popular series among the “best second-place” matchups.
Who will crack under the pressure?
Created by humans, assisted by AI.
(@BryanHoch)