The AL East has one of the most stacked divisions in all of MLB right now. Emerging as the top landing site after their World Series run as underdogs are the Toronto Blue Jays. However, for the Jays, keeping pace in the stacked AL East might mean making an enemy in the Boston Red Sox and putting one of their own nine-figure stars on the trading block, according to Craig Borden of Jays Latest.

“We have team control if you trade for Brendan Donovan, who has only his second year of arbitration,” Borden said. “He’d have one more season with the Blue Jays. This would be a nice sneaky move for the Blue Jays to keep pace. If they get Bo Bichette, maybe Andres Gimenez becomes a trade chip.”

The Boston Red Sox have pursued Brendan Donovan throughout the offseason, seeking a second baseman to pair with Trevor Story. Donovan, 28, batted .287 over 118 games in 2025 with 10 home runs, 50 RBIs, and 64 runs scored. His wRC+ was 118, and he posted a 2.7 WAR while maintaining a .353 on-base percentage. His OPS last season was .775, and he earned his first All-Star selection despite missing time with a left groin strain.

Over four seasons with St. Louis, he has hit .282 with 40 home runs, 202 RBIs, and 241 runs, maintaining consistent on-base skills. His contact-first approach and left-handed bat address Toronto’s struggles with left-handed hitters in 2025, particularly against southpaws.

With two years of team control remaining at a $14 million total salary, Donovan represents a cost-controlled asset for Boston with his 2026 arbitration contract of 1 yr(s)/ $5,750,000.

Now, the Toronto Blue Jays have entered the race for Donovan, aiming to strengthen their lineup and positional versatility. The Gold Glove winner can play second base, third base, and left field, giving the Jays coverage if Bo Bichette departs or suffers an injury. If Toronto completes this trade, Donovan could slot near the top of the batting order and lengthen innings.

But there’s always a catch.

To accommodate him, Andres Gimenez becomes a pawn. The second baseman entered Toronto last season after a $106.5 million/7-year contract with Cleveland. But now, he may shift or become a trade chip, opening opportunities for roster flexibility. Potential trade components include Ricky Tiedemann, Joey Loperfido, Bowden Francis, Gage Stanifer, Addison Barger, or 2025 first-round pick JoJo Parker.

Toronto would need to deliver high-upside pitchers and MLB-ready prospects to satisfy the Cardinals’ rebuilding strategy and younger player targets.

The trade would provide immediate lineup impact while complementing Toronto’s core, including Vladimir Guerrero Jr., Anthony Santander, and Alejandro Kirk. His versatility will allow manager John Schneider to mix positions freely and create depth against injuries or slumps.

If completed, this deal signals the Jays’ commitment to winning in 2026 while filling a critical offensive and defensive gap.

Brendan Donovan’s potential move to Toronto could redefine the AL East balance immediately and sharply. If the Jays land Donovan, John Schneider gains a Swiss Army bat while Boston watches helplessly.

The Blue Jays have a real opportunity to swing big with a Yankees trade

Toronto keeps talking about internal growth and patience, but there’s a point where restraint starts to look like hesitation. Across the division, New York has leverage it may not want to admit, and Toronto has assets it can finally afford to move to acquire a big piece from an opponent.

Jazz Chisholm Jr. delivered a 2025 season with 31 home runs and 31 stolen bases. The Yankees hold contractual control through 2026, with arbitration projections pointing toward a significant salary increase. With roster balance tightening, New York has explored scenarios where peak value can be converted elsewhere.

That context frames how a dynamic middle infielder suddenly sits at the center of offseason movement.

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Meanwhile, Toronto enters this picture with controllable depth, payroll flexibility, and an opening across multiple defensive positions. Chisholm logged above-average defensive metrics while posting an OPS consistent with elite second-base production levels. Proposed frameworks send Toronto established performance while New York receives cost-controlled talent and long-term pitching upside.

Between patience and pressure, Jazz Chisholm Jr. has become the league’s most inconvenient arithmetic problem. The Blue Jays see flexibility and control, while the Yankees quietly see leverage evaporating. If Toronto and New York act decisively, this trade writes itself seamlessly.