Aug 30, 2025; Chicago, Illinois, USA; New York Yankees designated hitter Aaron Judge (99) celebrates in the dugout after hitting a solo home run against the Chicago White Sox during the fourth inning at Rate Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images Kamil Krzaczynski-Imagn Images

MLB Insiders Make Bold Yankees Playoff Predictions

Originally posted on New York Yankees on SI
By Michael Rosenstein | Last updated Sep 2, 2025 3:00 PM ET

So you're saying there's a chance? ESPN's MLB insiders made their bold predictions for the stretch run and the New York Yankees are going to like what some of the experts had to say.

"Actually, the Yankees will win the AL East," Alden Gonzalez said, when asked for his one bold prediction.

"Not only do the Yankees overtake Toronto for the division title, but they also grab a first-round bye, even if they can't quite catch the Tigers for the No. 1 seed," Tristan Cockcroft added.

Kamil Krzaczynski-Imagn Images

But not everyone jumped on the Yankees bandwagon.

"The top seed, based on the standings, is likely to be the Tigers or the Blue Jays, with the Boston Red Sox, New York Yankees, Houston Astros and Seattle Mariners all within plausible striking distance," Jeff Passan said.

"The Yankees have such a soft schedule in the final weeks that they wind up with the second-best record in the AL ... but because Toronto holds on to win the division, New York is the No. 4 seed and faces Boston in the wild-card round," Buster Olney said.

"The Red Sox will catch the Blue Jays and win the AL East," David Schoenfield predicted.

On Sunday, USA Today's Bob Nightengale offered his forecast for the AL East.

"(The Blue Jays) have opened the door of late for the surging Boston Red Sox and Yankees, going just 11-11 in August outside their three-game demolition of the Rockies," Nightengale wrote.

"The sizzling Red Sox are the team to watch in the AL East, and have three games left against the Blue Jays in Toronto the final week of the season," Nightengale added. "Yet, those are the only games the Blue Jays will play against contenders the final 16 games of the season."

The Yankees woke up Tuesday tied for second place in the AL East, two-and-a-half games behind the Blue Jays. New York is tied with Boston atop the AL Wild Card standings.

Kamil Krzaczynski-Imagn Images

Manager Aaron Boone and company have a tough stretch on deck: three games at the first-place Houston Astros, three games at home vs. the first-place Blue Jays, three games at home vs. the first-place Detroit Tigers and three games at the Red Sox.

The Yankees have already lost their season series to the Red Sox (2-8) and Blue Jays (3-7).

However the schedule will soften for the Yankees, who end the season with 10 straight games against last-place teams: at the Baltimore Orioles (Sept. 18-21), home vs. the Chicago White Sox (Sept. 23-25) and home vs. the Orioles (Sept. 26-28).

Also on the plus side, FanGraphs gives the Yankees a 99% chance of making the playoffs. New York leads the AL with an 11.9% chance of reaching the World Series. Only the Los Angeles Dodgers (18.1%) have better World Series odds.

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