Inside The Pinstripes

Yankees Will Ride Schedule Weakness to Playoffs

One MLB insider is predicting the New York Yankees will make it to the playoffs because of their weak remaining schedule.
Aug 13, 2025; Bronx, New York, USA; A view of a battling helmet held by New York Yankees left fielder Jasson Dominguez (24) during the ninth inning against the Minnesota Twins  at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images
Aug 13, 2025; Bronx, New York, USA; A view of a battling helmet held by New York Yankees left fielder Jasson Dominguez (24) during the ninth inning against the Minnesota Twins at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | Vincent Carchietta-Imagn Images

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The New York Yankees have not been playing their best baseball lately, and it's becoming a problem. They're 6.5 games behind the Toronto Blue Jays in the AL East (a far cry from the beginning of the season, which saw the Pinstripes leading the league by as many as seven games) and just barely sneaking past the Cleveland Guardians into the AL Wild Card, with a win percentage that is just .004% better.

Is it possible that the Yankees won't make it into the post-season, despite finishing last season as AL Champions? Fans can breathe a — small — sigh of relief: some signs are pointing to yes. ESPN insider Buster Olney wrote recently that the Yankees would make it to the post-season: but only because the rest of their schedule is the easiest in the league.

"The Yankees are three-quarters of the way through their schedule and Aaron Boone is still trying to figure out his bullpen — a tough place for any team to be in a pennant race, let alone the defending AL champions," he wrote. "But we can look back at the '21 Atlanta Braves and the '23 Rangers and Arizona Diamondbacks for this reminder: It is possible to find yourself late in the season. It is possible to have a turnaround. And the landscape in front of the Yankees might be as friendly as we've ever seen for a pennant contender."

New York Yankees designated hitter Aaron Judge
Aug 11, 2025; Bronx, New York, USA; New York Yankees designated hitter Aaron Judge (99) reacts after striking out during the fifth inning against the Minnesota Twins at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

New York is experiencing weaknesses on both sides of the ball that occasionally culminate into a perfect storm. A strong pitching performance can sometimes make up for difficulty getting batters on base and relying on home runs from super stars like Aaron Judge and Giancarlo Stanton, and vice-versa. However, on days where the offense seemingly decided to stay home and the bullpen gives up four runs in two innings, things look dire.

Fortunately, as Olney pointed out, the Yankees are up against an incredibly weak August and September schedule. While there's plenty of division matchups, there's also forthcoming series against the Chicago White Sox and Minnesota Twins, two of the weakest teams in all of baseball. The Yankees should be able to pull off some easy wins against these teams and make it into the post-season.

"Don't be surprised if the Yankees finish the regular season with a flourish, and at least defer some of the big-picture questions that always hover over N.Y. teams," Olney wrote.

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Delilah Bourque
DELILAH BOURQUE

Delilah Bourque is a writer and copyeditor based out of Pittsburgh, PA. She received her Bachelor's degree from the University of Pittsburgh in 2021. After a few years in corporate marketing, she joined On SI as a full-time copyeditor and contributor to the New York Yankees On SI, as well as occasional contributions across the Pittsburgh Pirates and Pittsburgh Steelers on SI.