Bo Bichette, the Blue Jays SS who just announced he’ll return from injury to play in the World Series, will hit free agency this winter. Since then, there have been whispers about what the best place for him could be. One name that popped up was the Yankees. But here’s the twist: with Anthony Volpe sidelined following shoulder surgery and Brian Cashman sitting on roughly $70 million in payroll space, the NYY might look elsewhere.

The Yankees have some financial flexibility. GM Brian Cashman has about $70 million to spend before facing a $300 million luxury tax. While the team can make a significant acquisition, any move must align with its long-term goals. And Bo Bichette won’t be cheap because he’s in his last arbitration years before free agency. His contract might go around $180M and his numbers will tell you exactly why. He has an average of .311, 18 home runs, and 94 RBIs in 2025. Adding another expensive star to a franchise that already has a lot of hefty contracts is no less than a gamble when there are many other loopholes.

That’s where things get complicated. According to Chris Kirschner of The Athletic, the Yankees’ real needs stretch beyond shortstop. He wrote, “The Yankees’ biggest needs include a center fielder, remaking the back end of their bullpen, replenishing the bench and possibly adding a starting pitcher.” “With Volpe’s shoulder surgery delaying his 2026 season, it’s possible they add a shortstop. But don’t expect a player at the top of the market like Bo Bichette.”

A lot of that uncertainty comes from Anthony Volpe’s condition. After a tough season, he underwent shoulder surgery. The 24-year-old posted a batting average of only .212 with 19 home runs and 72 RBIs, indicating he was not consistent at the plate. And on the field? Volpe used to be seen as a key part of the defense, but his Outs Above Average dropped to -7, and he had trouble with simple plays. This has raised many eyebrows.

Bo Bichette’s bat would undoubtedly upgrade the lineup. But the Yankees front office now has to make a big choice with improvement needed in almost every department.

With Bichette likely off the table and Volpe’s return timeline uncertain, the Yankees could explore more creative solutions—younger, cost-controlled talent that fits their developmental philosophy without breaking the bank.

Turning to a younger option: Josh Kasevich

If the NYY choose not to sign Bo Bichette, they might look for a younger player up north who fits their budget and developmental attitude.

Josh Kasevich, a 24-year-old player in the Toronto Blue Jays system, hit .325 with an .815 OPS in 41 Triple-A games before a back ailment kept him out of action this season. His Triple-A average dropped to .173 in 29 games after his injury, but he bounced back in the Arizona Fall League, when he again showed exit speeds over 100 mph. That mix of potential and danger might make him a good target for the Yankees, who need shortstops.

Kasevich may not be safe on Toronto’s 40-man roster this winter because their infield is full. This means the Yankees could take him in the Rule 5 Draft. The point is that New York would have to keep him on their active roster for all of 2026 or give him back, which makes it a higher-risk, higher-reward move. This cheaper option demonstrates a willingness to grow instead of just buying past the difficulty, given their flexibility and Volpe’s problems.

Well, if the Yankees don’t want to go for Bo Bichette due to the contract, they might look at Josh Kasevich. On the contrary, the Blue Jays must find a way to protect this young talent before he slips through their fingers in the Rule 5 Draft.