The Toronto Blue Jays enter late May 2025 at a crossroads. Hovering around .500 with a 22-23 record, they remain within striking distance in the American League East, but the margin for error is razor-thin. The front office faces a pivotal decision: double down for a playoff push or pivot toward the future by leveraging valuable assets before the trade deadline. As the season unfolds, one name stands out above all others as the player Toronto must trade before the 2025 deadline, Bo Bichette.

The Blue Jays’ Most Valuable Trade Chip

Toronto Blue Jays shortstop Bo Bichette (11) throws out Tampa Bay Rays left fielder Chandler Simpson (not shown) in the fifth inning at Rogers Centre.
Dan Hamilton-Imagn Images

Since his debut in 2019, Bo Bichette has been a cornerstone of the Blue Jays’ infield, posting a career .296 batting average, two All-Star nods, and a pair of league-leading seasons in hits. His offensive consistency, coupled with solid defense at shortstop, has made him one of the most productive players at his position. Yet, the very qualities that make Bichette indispensable on the field also make him Toronto’s most attractive trade chip off it.

Bichette is in the final year of a three-year, $33 million contract and is poised to command a massive deal in free agency, potentially in the $200 million range. While the Blue Jays managed to extend Vladimir Guerrero Jr. with a record-setting contract, they have not come close to a long-term agreement with Bichette. With free agency looming and no extension in sight, the risk of losing Bichette for nothing grows with each passing day.

The logic for trading Bichette is both practical and strategic. Toronto’s window to contend with its current core is closing, and the farm system needs replenishing. The Guerrero extension has likely shifted the team’s financial priorities, making it increasingly difficult to justify another mega-deal for Bichette. If the Blue Jays fall further out of contention by July, holding onto Bichette becomes a gamble with diminishing returns.

Moreover, Bichette’s market value is peaking. He’s off to a strong start in 2025, hitting .291 with impressive underlying metrics, ranking in the 90th percentile or higher in expected batting average, slugging, and strikeout rate. Multiple contenders, including the Dodgers and Yankees, are already circling, and the market for a productive, playoff-tested shortstop is always robust. Waiting risks injury or a slump that could erode his value.

The Trade Proposal

While the Dodgers have been frequently linked to Bichette, the New York Yankees present the most compelling trade partner. The Yankees are contending, have a glaring need on the infield, and boast the prospect capital to make a deal happen. With Oswaldo Cabrera sidelined and the AL East wide open, New York is motivated to act aggressively.

Proposed Trade:

Blue Jays receive:

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  • George Lombard Jr. (SS, Yankees No. 1 prospect)

  • Spencer Jones (OF, Yankees No. 2 prospect)

  • Ben Hess (RHP, Yankees No. 7 prospect)

Yankees receive:

  • Bo Bichette (SS)

This package gives Toronto a franchise shortstop prospect in Lombard Jr., a potential middle-of-the-order bat in Jones, and a high-upside arm in Hess. Lombard Jr. is a polished 19-year-old with elite defensive instincts and a developing bat, while Jones draws comparisons to Aaron Judge for his size and power potential. Hess, meanwhile, brings swing-and-miss stuff and could slot into Toronto’s rotation within a year or two.

For the Yankees, Bichette fills a critical need at either shortstop or third base, depending on how they configure their infield. He immediately upgrades their lineup and provides a potent right-handed bat for the postseason push. If New York is serious about keeping pace with the league’s elite, acquiring Bichette is the type of bold move that could define their season.

Trading a homegrown star is never easy. Bichette is not only a fan favorite but also a proven performer in high-leverage situations. However, the alternative—losing him for a compensatory draft pick in free agency—would be a bitter pill for the franchise and its supporters. By acting decisively at the deadline, the Blue Jays can accelerate their next competitive cycle and avoid a prolonged rebuild.

The proposed deal also aligns with Toronto’s recent strategy. After securing Guerrero Jr. as the face of the franchise, the Blue Jays can now retool around him while adding premium young talent. Lombard Jr. and Jones could both be MLB-ready within two seasons, giving Toronto a dynamic new core to build around.

As the 2025 trade deadline approaches, the Blue Jays must make a difficult but necessary decision. Bo Bichette’s value is at its apex, and the market is ripe for a blockbuster deal. By trading Bichette to the Yankees for a package headlined by George Lombard Jr. and Spencer Jones, Toronto can set itself up for long-term success while maximizing the return for one of the game’s most talented shortstops. The time to act is now, before opportunity slips away and the Blue Jays are left with nothing but memories of what might have been.