The greatest rivalry in sports will see its next installment this October, as the Yankees and Red Sox are slated to square off in the American League Wild Card Round.
This rivalry is so enticing because it is more than organization vs. organization. It’s a series of one-on-one matchups, of players rising or falling in the moment. It is Derek Jeter vs. Nomar Garciaparra, Pedro Martinez vs. Don Zimmer, Bucky Dent vs. the city of Boston.
With the next chapter a blank page for now, let’s examine the top matchups in the 2026 Yankees/Sox series.
Ben Rice vs. Sonny Gray
Ben Rice has been one of the few bright spots in the Yankees’ order this season. He’s having the best season of his career and is the only Yankee hitter who hasn’t missed any time. He’s set career highs in home runs (39) and runs batted in (95), and ranks high across the board in various American League Categories, including second place in slugging (.525).
Meanwhile, Sonny Gray has been an anchor in the Boston rotation all season. He leads baseball in wins (17) and sports a more-than-respectable 2.82 ERA. After joining the Red Sox in free agency this off-season, the ex-Yankee talked negatively about his time in New York.
Between his 2025 with the Cardinals and this year with the Red Sox, Gray has started three games against a Ben Rice lineup. Rice is three-for-seven with two walks and two home runs off of the right-hander. Good for a slash line of .429/.556/1.286. In a short, best-of-three series like this one, every at-bat has heightened value. With Gray the only viable right-handed starter, that could spell trouble for the Yankees.
The game that Gray gets the ball is Rice’s best opportunity to help the Yankees take a game. Last year, the Red Sox lined up their matchups to keep him out of game one entirely. Of course, Rice isn’t as drastic of a platoon hitter this year, but his OPS is .150 points higher against right-handed pitching.
Max Fried vs. Trevor Story
Max Fried has been amazing in his first two seasons in the Bronx. He missed time with injury this year, but he’s still posted a 2.80 ERA in 20 starts. In five games against the Red Sox while wearing pinstripes, he’s tossed 30 innings and allowed five earned runs, good for a 1.50 ERA.
He threw 6.1 scoreless innings in game one last year, and he’s got great individual numbers against pretty much every Boston hitter. Including Trevor Story. Story is the highest-paid hitter in the Red Sox lineup and hasn’t produced at a level that matches his salary. 2026 was his fifth season in Boston, and he hit just five home runs. He’s played more than 100 games in only one of those years.
In 19 career at-bats with Fried on the mound, he has just four hits (.211 batting average). Boston fans still have a glimmer of hope: two of those hits cleared the fence. If Story can run into one at the right time and take a Max Fried curveball deep to swing the score in his team’s favor, it might just be enough to eliminate the Yankees.
Paul Goldschmidt vs. the Young Southpaws
Father time has been no match for Paul Goldschmidt in his 38-year-old season. He may not have the same power output that he once did, with only 31 extra-base hits, but he has been a valuable asset for manager Aaron Boone to deploy against left-handed pitching.
He slashes .307/.402/.588 against left-handers in 2026, with his .990 OPS in that split sixth in baseball (min. 150 PA vs LHP). He’s started 47 of the Yankees’ 54 games against southpaw starters, and he’s second on the team with 15 pinch-hit at-bats. He has his role on this Yankees team, and he performs very well at it.
That is, except for Payton Tolle and Jake Bennett, a pair of rookie left-handers for the Red Sox. Both have had very good seasons and are expected to get down-ballot Rookie of the Year votes. They’ll play a prominent role in Boston’s October plans.
Goldschmidt has nine at-bats against the pair, six against Bennett and three against Tolle. He’s hitless. With a Yankee lineup missing a powerful right-handed bat because Aaron Judge and Giancarlo Stanton are unable to escape the injured list, Goldschmidt has been the remedy this year.
If Chad Tracy were to throw one of Tolle and Bennett, surely one of Rice and Luis Garcia Jr. would find themselves out of the lineup in Goldschmidt’s favor. In that case, Yankees fans shouldn’t expect a big night from their veteran first baseman.
Cam Schlittler vs. the Boston Media
The emergence of Cam Schlittler seemingly came out of nowhere. He was never a big-name prospect, and he didn’t even have a proper rookie season. Then, suddenly, he was on the mound in the winner-take-all Game 3 of last year’s Wild Card round.
Of course, he shoved for eight scoreless innings and vaulted himself into the national spotlight. He’s now the ace of a Yankee team that has spent over $600,000 on its rotation; he’s all but been handed the Cy Young award, and he has an outside shot at the MVP.
Boston fans hate him. Primarily because he was one. Schlittler was born in Massachusetts, grew up a Red Sox fan and played college ball at Northeastern.
He took particular objection to certain comments he heard during that playoff start in 2025.
More recently, after the Yankees and Red Sox wrapped up their regular season series, he got into an online spat with Anna Caruso of the Section 10 podcast.
With plenty of animosity between the fan bases to begin with, Boston’s distaste for baseball’s best pitcher will only raise tensions under the playoff spotlight.
Yankees Brass vs. Aroldis Chapman
Aroldis Chapman saved 153 games in pinstripes between 2016 and 2022. Only Mariano Rivera and Dave Righetti have more as a Yankee. His tenure in New York ended on a sour note, as he missed a team workout ahead of the 2022 postseason and was subsequently left off the roster.
On Chapman’s side of the story, he claims that he had permission to travel down to Miami and therefore felt his punishment was unjust.
Earlier in the season, before the Red Sox fired off a July record of 25-4, Chapman was rumored to be dealt, and the Yankees needed bullpen help.
When asked about a potential reunion with the Yankees, Chapman was less than thrilled.
“No way. If I were told that I was being traded to New York, I’d pack my things and go home. I’ll retire right on the spot if that happens. I’m not crazy. Never again,” Chapman said.
He also said that before he’d ever consider a trade, “someone from [the Yankees] organization should apologize first.”
Later clarifying that the “someone” should be general manager Brian Cashman.
Meanwhile, Boone takes the credit for the move.
“I made the decision based on a lot of things and thought to leave him off because I thought that was the right thing to do for our club at the time,” Boone said. “It’s water under the bridge for me.”
Whatever the case, it’s clear that Chapman doesn’t look back fondly on his time in the Bronx. We’ll see if a late-inning shutdown or meltdown from Chapman turns into more soundbites from him, Boone or Cashman.
Game one of the 2026 American League Wild Card round will be Tuesday, Sept. 29.
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