The New York Yankees are looking to use free agency to come back stronger than ever in 2026. While the Pinstripes have been connected most notably to heavy-hitting outfielders like Kyle Tucker and flame-throwing starting pitchers like Tarik Skubal, there are other positions where they can add; name, shortstop.

The Yankees’ current starting shortstop, Anthony Volpe, had a host of troubles in both 2025 and 2024. Now, New York is predicted to get a big name from a division rival: Toronto Blue Jays shortstop Bo Bichette.

Anthony Volpe’s 2025 Struggles

Volpe was the target of much ire from Yankees fans and baseball analysts alike this season. While he slammed 19 home runs in 153 games, he also committed 19 errors, tying for third-most in the league. Volpe’s other offensive stats weren’t great either, and he slashed just .212/ .272/ .391 for an OPS of .663 in the regular season.

Oct 2, 2025; Bronx, New York, USA; Boston Red Sox shortstop Trevor Story (10) is forced out at second base by New York Yankees shortstop Anthony Volpe (11) in the sixth inning during game three of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images / Vincent Carchietta-Imagn Images

Now, the Yankees have revealed that Volpe was dealing with a partial labrum tear in his non-throwing left arm all season. He’s since undergone surgery and is expected to miss the beginning of the 2026 season. While Yankees manager Aaron Boone denied that the injury impact Volpe’s play, general manager Brian Cashman directly contradicted him, saying he believes it did.

What Could Bo Bichette Bring to the Yankees?

Bichette boasted much better numbers than Volpe during the regular season, slashing .311/ .357/ .483 for an OPS of .840, his best numbers since his 2019 debut. While he committed 12 errors and isn’t a perfect defender, he’d bring a stronger bat to a team that was constantly criticized for leaving Volpe in the lineup.

Oct 27, 2025; Los Angeles, California, USA; Toronto Blue Jays second baseman Bo Bichette (11) hits an RBI single against the Los Angeles Dodgers in the seventh inning during game three of the 2025 MLB World Series at Dodger Stadium. Mandatory Credit: Jayne Kamin-Oncea-Imagn Images / Jayne Kamin-Oncea-Imagn Images

There’s downsides, though. Jim Bowden of The Athletic predicted that Bichette could command a contract worth $190 million over seven years, a much bigger spend than Volpe, who is set to make $3.25 million in 2026. Bichette is also injury prone, missing half the 2024 season due to various injuries.

While Bichette is a better bat than Volpe, it might be risky to spend a ton of money on a player who could get injured again when an existing player may bounce back after recovering fully himself. Plus, Bichette has made it clear he does not want to leave Toronto, a team he could very well win the World Series with in less than a week. The Yankees have five days after the end of the World Series before being able to sign free agents from other teams, including Bichette.