As the regular season inches toward an end, the New York Yankees are at a crucial point where manager Aaron Boone must make important choices that could change the team’s roster. The Bronx Bombers are 92-68 and in a tight race for the division title. They are pushing toward the playoffs while two of their key players are at the center of contract talks that will shape the team’s future.

Trent Grisham signed a one-year, $5 million deal with the New York Yankees, and his breakout performance has become one of the most interesting storylines of the season. The 28-year-old center fielder has gone from being a defensive specialist with little offensive potential to a real power threat who has won over both management and fans. This is exemplified by the fact that he has hit a career-high 34 homers so far this season.

Boone’s evaluation of Grisham shows how much faith the team has in the outfielder. “I mean, I’ve loved getting to manage him,” Boone stated, emphasizing the consistency in Grisham’s character. “He’s a really good competitor. Very easy going, very laid back – he’s got that chill vibe, that ‘big sleep’ mentality. But Trent competes really well, and he likes the action. He likes it when the chips are down.” The manager’s confidence extends to crucial moments, noting, “He’s certainly a guy we like up there when it matters.”

Boone praised both Grisham’s defensive contributions and offensive breakthrough, saying, “Obviously, there’s what he brings defensively in center field, and on top of it, I’m just super excited for him having a career year this year. Another big reason why we’re in this position is his excellence this year.” This dramatic turnaround from his struggles demonstrates both his resilience and the Yankees’ patience in developing talent.

Despite this breakout year for Grisham, question marks are being raised over his future with the Yankees. Grisham’s current contract runs out at the end of this season, but the  Yankees have an option to keep him for another year with a qualifying offer of $22 million. The kicker? There is a fear in the Yankees front office that this represents a significant gamble, as this might just be a one-season surge, and chances are that he will drop down to his average standards.

So what’s the solution? A new short-term deal will serve both parties, as suggested by FanSided’s Stephen Perello. “A one-year gamble might be the best for both sides. For the Yankees, it would give them the chance to see if Grisham’s breakout is real, while Grisham could hit the open market again after 2026 (heading into his age-30 campaign), potentially with two years of strong production driving his price tag up further,” stated Parello.

Perello also pointed out that a qualifying offer could limit Grisham’s options with other clubs. Since signing him would require draft pick compensation, the rival teams may hesitate, making a short-term deal an ideal solution for both.

Grisham isn’t the only Yankees player whose future beyond this season is in doubt.

The Yankees are also dealing with Cody Bellinger’s new contract

The Yankees’ biggest problem this offseason is Cody Bellinger’s contract situation. Bellinger can choose to give up a $25 million salary and become a free agent as he enters the last year of his three-year, $80 million deal he signed with the Cubs. Jon Heyman, an MLB insider, said he “surely” will. Bellinger has hit .272/.324/.489 with 24 home runs in 121 games with the Yankees.

The Yankees organization has to deal with the uncomfortable truth that their investment in Bellinger could lead to his departure. This would mean that they would have to deal with both his potential exit and the difficulty of replacing his production while staying within the salary cap in a market that is becoming more competitive.

Even though there are still some questions about the roster, the Yankees have found stability in their franchise cornerstone. One player continues to be a strong leader both on and off the field, despite management’s struggles with contract decisions that could impact the team’s future.