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By Jackson Roberts
Contributing Sports Writer
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For the New York Yankees, Trent Grisham represents one of the more interesting free agency conundrums in recent memory.
Grisham had a breakout season at age 28, posting 34 home runs, an .811 OPS, and 3.5 wins above replacement. He was the Yankees' typical leadoff hitter against right-handed pitching, despite being nothing more than a throw-in alongside Juan Soto in the December 2023 trade with the San Diego Padres.
Now that Grisham has reached free agency, though, the Yankees have to not only decide whether to try and bring him back, but whether he's worth the one-year, $22.05 million qualifying offer that would entitle them to draft pick compensation if he rejected it and signed elsewhere.
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The additional necessary context is that the Yankees have two main free agent outfielders to be concerned about, and as productive as Grisham was in New York this season, the team is likely more focused on retaining two-time All-Star and former Most Valuable Player Cody Bellinger.
New York Post insider Joel Sherman had an interesting take on the situation on Tuesday. Sherman believes the Yankees should give Grisham the qualifying offer, in part because they could try to trade him if and when Bellinger re-signs with the club later in the free-agency window.
"If Grisham accepts the qualifying offer and the Yankees ultimately sign Bellinger, I do not think it is impossible for the Yanks to trade Grisham," Sherman wrote. "They would have to take a salary back or eat some money, but center field and offense are in short supply, so as long as it is not the full $22.05 million, then I could see the Yanks being able to move Grisham."
Sherman also went on to posit a hypothetical scenario in which it might make sense for the Yankees and New York Mets to swap Grisham and starting pitcher Clay Holmes, who has a significantly lower salary than that $22 million qualifying offer, but an opt-out after the upcoming season.
In theory, it would likely have to be another big-market team to acquire such a large chunk of payroll, even on just a one-year commitment. The Philadelphia Phillies, speculatively, would be another interesting fit, as they've gone without an above-average starting center fielder or platoon for several years running.
Qualifying offer decisions are due five days after the conclusion of the World Series, so we'll know soon whether there's any chance the Yankees are humoring the idea Sherman proposes.
More MLB: Yankees Insider Throws Out Surprise Trade Possibility for 30-30 All-Star
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