Inside The Pinstripes

Yankees AL East Chances Improve

The New York Yankees clinched a postseason berth with this latest win, and they have a shot at the postseason if they play their cards right.
Sep 23, 2025; Bronx, New York, USA; New York Yankees shortstop Jose Caballero (72) reacts after hitting a walk off single against the Chicago White Sox during the ninth inning at Yankee Stadium. Mandatory Credit: John Jones-Imagn Images
Sep 23, 2025; Bronx, New York, USA; New York Yankees shortstop Jose Caballero (72) reacts after hitting a walk off single against the Chicago White Sox during the ninth inning at Yankee Stadium. Mandatory Credit: John Jones-Imagn Images | John Jones-Imagn Images

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With their latest nail-biting victory over the Chicago White Sox, the New York Yankees find themselves just one game behind the AL East-leading Toronto Blue Jays with five games to go. The win clinched them a spot in the playoffs, and the possibilities down the stretch are looking more promising.

After the game, The Athletic's Chris Kirschner posted the latest in his series of AL East scenario Tweets, including the five outcomes where the Yankees manage to take the division.

"Yankees have 5 games remaining. A look at whether the division remains in play:
Yankees go 5-0, win division if Blue Jays finish 3-2

Yankees go 4-1, win division if Blue Jays finish 2-3

Yankees go 3-2, win division if Blue Jays finish 1-4

Yankees go 2-3, win division if Blue Jays finish 0-5"

Toronto will face off against the third place Boston Red Sox for two more games before a three-game series with the Detroit Tigers, currently in third place in the AL Wild Card. Under Kirschner's Tweet, one fan commented, "I'm the biggest Red Sox Fan in the world the next two days."

With a playoff berth guaranteed, the Yankees will finish their series with the White Sox before hosting the Baltimore Orioles, who they defeated 3-1 in their last series. The Yankees are still determining who their third starting pitcher might be for the third game of a potential Wild Card series, with Max Fried and Carlos Rodón considered to be certain. The battle over the next five games will take place between Cam Schlittler and Luis Gil, who started in this latest win against the White Sox.

New York Yankees shortstop Jose Caballero
Sep 23, 2025; Bronx, New York, USA; New York Yankees shortstop Jose Caballero (72) reacts after hitting a walk off single against the Chicago White Sox during the ninth inning at Yankee Stadium. Mandatory Credit: John Jones-Imagn Images | John Jones-Imagn Images

Trade deadline acquisition and beloved Yankees pest Jose Caballero had the last word in this crucial victory, with a bottom of the ninth single to score Aaron Judge. It was a nail-biting finish that began 2-1 Sox and ended 3-2 Yankees. Caballero, drenched in champagne, shared his joy in the moment after the game.

“It’s amazing. It’s the best feeling I ever had,” Caballero said, h/t Gary Phillips of the New York Daily News. “It’s my first time in the postseason, so I’m just trying to enjoy my time.”

After chasing the Blue Jays around all season — at times fully 6.5 games behind them in the AL East — the possibility of catching them at the last second is surprising. The Blue Jays have the tie breaker, so the Yankees will need some urgency to make the best use of this last week.

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Published
Erin Shapland
ERIN SHAPLAND

Erin covers the New York Yankees for On SI, reporting on all aspects of the championship chase that comes with a storied franchise. A fan of all storylines, who's looking to bring the latest news and updates to one of professional sports' greatest fanbases.