As the 2026 MLB free agency period approaches, excitement is building around Chicago Cubs outfielder Kyle Tucker. The three-time All-Star is having a standout season, perfectly timed to maximize his market value. Tucker’s impressive blend of power, speed, and defensive reliability places him among the top five MVP contenders, with industry experts suggesting he might secure one of the largest contracts in baseball history.

Former MLB executive and current analyst Jim Bowden predicts that Tucker’s upcoming contract could rival or surpass the monumental deals recently given to Juan Soto ($765M) and Vladimir Guerrero Jr. ($500M). “He’s on track for another 30-30 season,” Bowden noted. “With his credentials, he’s in line for a nine-figure contract starting with a six.” This puts Tucker in discussions for a deal exceeding $600M, making him highly sought after.

The Yankees are preparing for another significant acquisition. After missing out on Juan Soto, who joined the Mets in a sensational move, the Yankees seem ready to make another bold attempt. Bowden points to the Yankees as strong contenders for acquiring Tucker, along with other major-market teams like the Dodgers, Phillies, and even the Cubs. The Yankees, known for their pursuit of top-tier talent, find Tucker appealing due to his age, performance, and potential. His all-around game—offense, defense, and base running—makes him an ideal target for a team looking to construct a long-term powerhouse.

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Beyond Tucker, the Yankees are also eyeing other 2026 free agents, such as Alex Bregman and Bo Bichette. Bichette might need to change positions to fit into the Yankees’ infield but could still command a significant contract due to his hitting prowess. “He would need to transition to third base for teams like the Yankees,” Bowden mentions, “but a strong season keeps his value high.”

In contrast, rumors about the Yankees pursuing young Pirates ace Paul Skenes were dispelled this week. Jon Heyman reported that Pittsburgh has no intention of trading him: “No chance, no way, no how.” Nevertheless, with ambitious goals, the Yankees appear determined to make the 2026 offseason transformative, beginning with Kyle Tucker.