Inside The Pinstripes

Maybe Yankees Aren't Landing Blue Jays Star

The New York Yankees are still a big question mark for a Toronto Blue Jays star this offseason.
Nov 1, 2025; Toronto, Ontario, CAN; Toronto Blue Jays designated hitter Bo Bichette (11) runs after hitting a three run home run against the Los Angeles Dodgers in the third inning during game seven of the 2025 MLB World Series at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images
Nov 1, 2025; Toronto, Ontario, CAN; Toronto Blue Jays designated hitter Bo Bichette (11) runs after hitting a three run home run against the Los Angeles Dodgers in the third inning during game seven of the 2025 MLB World Series at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images | John E. Sokolowski-Imagn Images

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The New York Yankees' infield presents some big questions for the spring, and while they don't seem to be prioritizing the infield this offseason, they could still make some surprising moves.

MLB's Bryan Hoch recently hinted that while the Yankees would be taking on considerable cost in their already (potentially) tight budget, Toronto Blue Jays star shortstop Bo Bichette may not be out of the question for the Yankees infield.

"It's not a non-starter, but in talking to people around the Jays last year covering the ALCS, Bichette's not a long-term answer at shortstop [...]," Hoch wrote. "So you'd need to plan on him being your second baseman or third baseman, which means we're talking about a trade involving Jazz Chisholm, Jr. or Ryan McMahon if you're intending to keep payroll around the $310M window."

Toronto Blue Jays designated hitter Bo Bichette
Nov 1, 2025; Toronto, Ontario, CAN; Toronto Blue Jays designated hitter Bo Bichette (11) hits a three run home run against the Los Angeles Dodgers in the third inning during game seven of the 2025 MLB World Series at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images | John E. Sokolowski-Imagn Images

"Long story short, I don't expect to see it. But I will tell you what one Toronto person told me -- Bichette would be a good clubhouse fit and he'd handle New York well."

The Yankees' current shortstop options are Anthony Volpe (controversial and unavailable in the spring, but expected to reappear later in the season), Jose Caballero and Oswaldo Cabrera. The latter two are expected to test their talents this winter, and the Yankees have showed no signs publicly that they are dying to replace their shortstops.

Potential Chisholm Trade?

New York Yankees second baseman Jazz Chisholm Jr.
Oct 7, 2025; Bronx, New York, USA; New York Yankees second baseman Jazz Chisholm Jr. (13) hits a solo home run in the fifth inning against the Toronto Blue Jays during game three of the ALDS round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | Vincent Carchietta-Imagn Images

Hoch has alluded to the clubhouse atmosphere when referring to a potential Chisholm trade before, and Bichette may be part of an ideal makeup if we're excluding Chisholm. Chisholm is an undeniable talent, but the Yankees have not given him a contract extension after his 31 homer/31 stolen base season, and they might leverage him to meet some of their more pressing offseason needs.

"[...] as of right now, it seems like they're lukewarm about giving him a contract extension," Hoch said ahead of the winter meetings. "[...] If not, he could probably bring a significant return, he might be one of their best trade chips. Is he part of the Yankees for four to five years, and do they see his personality in the room for four to five years?"

Chisholm's big personality is an upside for some, and a downside for others. If they replace him at second, they still have the question mark at SS, but they also have an undeniable bat that just went on a World Series run with the Blue Jays. Bichette also bats right-handed, a trait the Yankees are actively shopping for. Bichette batted .311/ .357/ .483 with an .840 OPS this regular season, with 18 home runs and 94 RBIs.

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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.