Pitching matchups will be a major topic of conversation surrounding this week’s American League Wild Card Series between the New York Yankees and Boston Red Sox.
Phenoms such as presumptive American League Cy Young Award winner Cam Schlittler and rookie standout Payton Tolle are expected to make their presence felt in Game 1, but both lineups will need to provide the run support for these arms and their overall staffs throughout the series.
The Yankees’ offense will be under a particularly intense microscope. It is not known if they will have three-time AL MVP Aaron Judge will be on the series roster. Additionally, Trent Grisham's and Giancarlo Stanton's statuses are up in the air.
“It feels more so this year than probably any year where we do have a lot of questions to answer,” Yankees manager Aaron Boone told ESPN’s Jorge Castillo. “Like a lot of years, when you're going into the postseason, it feels like you're kind of arguing a lot of times over that 25th or 26th spot between a couple of different guys. … It does seem like there's more to work through this year.”
Regardless of the unknowns, New York’s lineup will need to step up while Boston attempts to keep them at bay. Given the number of southpaws they might face, if their upcoming showdown goes well, it could be a major indicator of a long October run.
The Yankees’ hitters will be tested against Boston’s left-handed pitchers

Outside of Tolle, Ranger Suarez is a left-handed talent slated to start a potential Game 3. Additionally, others like Jake Bennett and Aroldis Chapman will certainly challenge the Yankees’ largely left-handed lineup.
Amed Rosario, George Lombard Jr., Jose Caballero, and Anthony Volpe could all receive opportunities to make an impact.
This may be especially true as it pertains to Anthony Volpe, who has recently played second and third base while the team has continued to trust Lombard at shortstop. Across the last 15 games of his regular season, the 25-year-old hit one home run, posted a .291 OPS, and tallied nine RBIs.
Article Continues BelowBoone suggested that Volpe could see time at second in place of left-handed slugger Jazz Chisholm Jr.
“Volpe is very much in play. The platoon stuff is in play there,” Boone told Gary Phillips of the Daily News. “Obviously, Jazz is just coming back from the thumb [injury]. He was able to get a couple games in; would have liked another one or two, but the weather didn’t really cooperate this [past] weekend.
“Anthony’s put himself very much in the mix to be a part of the equation.”
For as much as the success or failure of righty batters will be critical, it could be argued that New York’s left-handed bats will be more indicative of the team’s ceiling. Ben Rice, Cody Bellinger, Luis Garcia Jr., and Austin Wells will have to hit in some capacity if the squad has designs on making a deep playoff run.
Bluntly, if the Bombers can score enough runs against Boston to place a strong rotation and serviceable bullpen in a solid spot, they should feel superb about their standing.
The Yankees bested the Red Sox in three games during last postseason’s Wild Card Series. It remains to be seen how their 2026 matchup will play out, but it is clear that the 2025 winner is aware of both the threat and opportunity in front of them.
“It's special to be a part of. It always is,” Boone said. “Even when you go there for a regular-season series, or they come here for a regular-season series, it always feels a little bit bigger, and now, back-to-back years, we're going up in this Wild Card series against them. It will be a great battle. They've had a great year and are a great team.”

