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The New York Yankees could get a major upgrade at shortstop by targeting this highly coveted free agent this winter.

The New York Yankees head into this offseason looking to upgrade across the board. While the club had a great regular season, the sour playoff exit has left GM Brian Cashman looking to figure out ways to improve.

This winter’s free-agent market shows some promising names that could help boost the Yankees’ lineup. But there’s one name in particular that could be a substantial boost.

That name is shortstop Bo Bichette. Bichette had a good bounce-back year with the Toronto Blue Jays this season. He came back from a couple of injury-filled seasons to regain the form he once showed as a promising prospect.

Bichette played in 139 games, clubbing 18 dingers in driving in 94 runs. Most importantly, he notched 181 hits, good for a .311 batting average.

Those encouraging numbers came despite missing most of September and the playoffs with a knee injury. But he returned during the World Series. His three-run jack in Game 7 nearly gave the Jays their third title.

Now, Bichette will test the free-agent waters. While the Blue Jays will likely do everything they can to keep the 28-year-old, other teams will certainly kick the tires. That’s where the Yankees can swoop in and bring in the former second-round pick.

The Yankees could use an upgrade at shortstop defensively and another solid bat in the lineup. Bichette offers both options while still offering several good years ahead of him.

Bichette Would Command Long-Term Deal from Yankees

Bo Bichette could likely commend a long-term deal from the Yankees. It’s tough to envision the still-young infielder taking a short-term deal. Unless the Yankees offered a three-year deal with an opt-out clause after the first or second year, it would take a long-term deal to land Bichette.

While the Yankees may not offer a 10-year deal, something along the lines of a six or seven-year deal could get the ball rolling. As for the dollar value, that’s a hard one to project. According to Tim Britton of The Athletic, Bichette could be looking at an eight-year deal worth around $212 million.

That’s not exactly pocket change. And it may be too rich for the Yankees’ britches. But then again, the Yanks could take a shot at bringing him in on a more affordable deal. That could be wishful thinking, however.

Bichette Likely to Remain with Blue Jays

The likeliest scenario is that Bichette remains with the Yankees’ division rival. The fit is just too good. Unless Bichette felt the Blue Jays’ World Series run this season was a one-off, he’s better suited remaining in Toronto.

If that’s the case, the best shot the Yankees would have to pry Bichette away would be to throw tons of cash at him. Considering this would be Bichette’s last shot at a big payday, the Yankees could be his best choice.

Of course, the Yankees will have plenty of pots in the fire this winter. But Bichette should be one that New York cannot afford to pass up. Naturally, that depends on whether or not he becomes available on the market.

Nestor Quixtan Seasoned NHL analyst and baseball writer focused on covering clubs across each league with news, analysis, and insights. Originally from Toronto, Canada, Nestor’s singular experiences and background have enabled him to bring a different take on the sports world as a whole. Nestor’s fondness for baseball and hockey set the tone for his love and passion for writing about sports. More about Nestor Quixtan

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