Timothe Chalamet has long been open about his love for New York sports — especially the Knicks as he was mobbed while leaving Madison Square Garden during the NBA playoffs — but lately, he’s watched heartbreak turn into déjà vu.

As he sat in the stands at Yankee Stadium on Wednesday night, he witnessed yet another New York team fall short — this time the Yankees, whose season ended in a 5–2 loss to the Toronto Blue Jays in Game 4 of the ALDS.

Chalamet’s Knicks fandom has been well documented: he’s become a familiar face courtside at Madison Square Garden, celebrating dramatic comebacks and bracing tough losses, and even standing out for a hilarious reason in May.

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During the 2025 Eastern Conference Finals, he went viral for his passionate reactions as the Knicks rallied from a 20-point halftime deficit — pumping his fists and shouting alongside fans as cameras panned to him on the broadcast.

That kind of emotional investment carries risk — and for Chalamet, the Yankees’ postseason collapse felt like déjà vu, echoing the Knicks’ own playoff heartbreak months earlier.

The Oscar-nominated actor was spotted in the stands alongside girlfriend Kylie Jenner, dressed in dark Yankees gear and cheering early when the game was tied.

But as the innings dragged on, the energy in The Bronx shifted from hopeful to somber. The Blue Jays’ bullpen smothered any Yankee momentum, shutting down late rallies and capitalizing on mistakes.

Rookie pitcher Cam Schlittler, who was sensational in the wild-card round against Boston, gave the Yankees a solid outing — 6 ⅓ innings, four runs (two earned) — but the offense never found its rhythm.

The Yankees’ bats once again went cold in a win-or-go-home moment. They managed just six hits to Toronto’s 12, repeatedly stranding runners and failing to capitalize on key opportunities.

Ryan McMahon’s solo home run in the third inning tied the game, but it would stand as one of the few bright moments for New York’s lineup.

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By the fifth inning, Toronto’s George Springer delivered a sacrifice fly to give the Blue Jays the lead, and they never looked back. Nathan Lukes and Vladimir Guerrero Jr. continued to torment Yankees pitching, stretching the lead to 5–1 by the eighth inning.

Aaron Judge tried to spark one final rally with an RBI double in the ninth, but it wasn’t enough. The 5–2 defeat sealed the Yankees’ elimination and extended their championship drought to 16 straight seasons.

Judge, who was emotional in his postgame comments, admitted the disappointment weighed heavily: “We fell short again. We had our chances — I take responsibility for that. You play here to win titles. That’s the only standard.”

For Chalamet, who’s become something of a good-luck charm at Knicks games, the loss marks the second time this year he’s watched a New York team’s season end in person.