Yankees Benched Their 2-Time All-Star Silver Slugger, And Now the Blue Jays Are Eyeing Him

Jazz Chisholm Jr., a two-time All-Star and Silver Slugger winner, had a postseason with the New York Yankees that was, to put it mildly, interesting. After struggling at the plate and defensively, he found himself left out of the starting lineup for multiple games, a major shake-up for a player of his caliber.

Postseason Struggles and Yankee Fan Frustration

Chisholm’s 2026 postseason run was a tough one. He struggled both offensively and defensively across his four appearances, leading manager Aaron Boone to bench him twice, even in their season-ending loss. Bleacher Report’s Zach Buckley highlighted Chisholm’s “up-and-down tenure” and said he “wasn’t great with the bat or the glove this postseason.” The frustration boiled over at Yankee Stadium when fans booed Chisholm after he fouled out as a pinch hitter in the seventh inning. Despite all this, Chisholm is a professional who didn’t let the decisions affect him. In fact, MLB Trade Rumors’ Connor Byrne reported that Chisholm “would rather continue his career with the Yankees than exit in free agency,” and he hopes to return next season as he hits free agency this winter.

Toronto’s Potential Free Agency Steal

With Chisholm hitting the open market, the Yankees have some decisions to make about his future, especially given he played last season on a $10 million contract. If New York decides to move on, Zach Buckley from Bleacher Report is predicting a surprising landing spot: the Toronto Blue Jays. This move could be massive for the Jays, even with Chisholm’s recent inconsistencies. Since the start of the 2025 season, he’s amassed 50 homers and 72 steals, showcasing that electrifying power and speed combo that makes him such a threat. He’s still young, set to turn 29 in February, which means “he could have more prime years ahead of him.” Adding Chisholm would provide Toronto with crucial defensive versatility and another big bat to pair with Vladimir Guerrero Jr., giving them an opportunity to compete for a World Series.

This winter, Chisholm has some big decisions ahead of him. Will the Yankees bring back their two-time All-Star after a tough postseason, or will he find a new home in Toronto and chase a World Series with the Blue Jays? It’s going to be wild to see where this goes.

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Originally reported by The Sporting News.