Blue Jays Star Free Agent Named Perfect Fit for Yankees in Nightmare Scenario

Could the Toronto Blue Jays really lose one of their best players to the New York Yankees?

David Reginek-Imagn Images

The Toronto Blue Jays head into the offseason with multiple huge questions as they're linked to just about every big name free agent not to mention already landing one, but one narrative stands out above the rest.

Following their first World Series appearance in over three decades in which they fell just short, Toronto is trying to add in free agency, however the biggest potential add here would be keeping Bo Bichette in the fold.

Bichette hits the open market following one of the best seasons of his career and near heroics after returning to the lineup from injury for the Fall Classic, and the expectation from most has been for the Blue Jays to bring him back.

Bichette wants to be in Toronto, and the organization wants to keep him, making this pretty cut and dry if the money can be worked out. In a recent article however, Mark Feinsand of MLB.com -- one of baseball's biggest insiders -- spun an absolute nightmare scenario and named Bichette as the best possible fit for the New York Yankees.

Yankees Could Steal Bichette Away from Blue Jays, Feinsand Says

Sep 5, 2025; Bronx, New York, USA; Toronto Blue Jays shortstop Bo Bichette (11) follows through on a broken bat RBI double against the New York Yankees during the first inning at Yankee Stadium. | Brad Penner-Imagn Images

"Bichette and the Blue Jays could still have a reunion, but what if the Yankees made a strong bid for the shortstop?" Feinsand asked. "Many view Bichette as a future second baseman, but with Anthony Volpe recovering from shoulder surgery and Jazz Chisholm Jr. set to become a free agent next year, Bichette could step in at shortstop and give New York a long-term plan at second base if Chisholm leaves."

After battling with New York for the American League East title before eliminating them in the postseason, losing Bichette to the most hated rival would be an absolutely devastating development headed into the 2026 season.

Bichette is among the best hitters in baseball, and not only would his departure from Toronto no matter who it was to sting, but he would potentially give the Yankees the piece they need to get back on top of the AL.

Blue Jays Losing Bichette to Yankees Would Be Worst Case Scenario

Nov 1, 2025; Toronto, Ontario, CAN; Toronto Blue Jays designated hitter Bo Bichette (11) throws to first for an out against Los Angeles Dodgers second baseman Tommy Edman (25) in the eighth inning during game seven of the 2025 MLB World Series at Rogers Centre. | John E. Sokolowski-Imagn Images

It's safe to say that if Toronto had to lose Bichette, him winding up in New York is the absolute last place fans north of the border would want to see. As Feinsand pointed out though, on top of the disgust of seeing a Blue Jays fan favorite in pinstripes, adding Bichette would give the Yankees a long-term second baseman who can hit if they moved him over.

Bichette rebounded from an ugly 2024 to have one of the best years of his career in 2025, posting a 3.5 bWAR in just 139 games. Prior to his September knee injury, the 27-year-old was on track to have a chance to lead the American League in hits for the third time in his career.

While both Toronto and Bichette want a reunion, sometimes this can be easier said than done, especially with the money the Blue Jays have already spent on Dylan Cease.

If Bichette really was to end up somewhere else, Toronto had better hope it's not with New York. Should this actually go down this way, general manager Ross Atkins -- and just about every other person in the city -- would wind up being sick to their stomachs.