The New York Yankees are entering the offseason with a familiar priority — fixing their outfield once again. They’ve already made headlines by offering Trent Grisham the $22 million qualifying offer, a move that raised eyebrows across the league.
It’s a calculated gamble, but one that could backfire if Grisham accepts it, forcing the Yankees to pay quadruple what they did last season for a player who’s still more potential than production.
Still, the Yankees aren’t done. Cody Bellinger remains at the top of their wish list, and according to multiple reports, they’d like to retain him before turning elsewhere. Bellinger’s price tag is expected to come in well below what Kyle Tucker will command on the open market, which keeps him firmly in play for a return to the Bronx.
Luis Robert Jr. enters the conversation
Even with Bellinger and Grisham on the table, the Yankees are exploring other possibilities. According to Ryan Garcia of Empire Sports Media, the team has legitimate interest in Chicago White Sox outfielder Luis Robert Jr. — a player with both tantalizing upside and plenty of question marks.
Robert, 28, is coming off a rocky 2025 campaign, hitting .223/.297/.364 with 14 home runs, 53 RBIs, and 33 stolen bases across 110 games. His overall offensive production dipped well below expectations, finishing 16% below league average. But his splits tell a more nuanced story — he hit .258 with six home runs in 93 at-bats against left-handed pitching, suggesting there’s still value in a platoon role.
What makes Robert intriguing for the Yankees isn’t just the offense, though — it’s the defense. He remains one of the best center fielders in the game, recording seven outs above average over 865.2 innings in center. His speed, instincts, and glove could anchor the outfield in a way the team hasn’t seen since Harrison Bader prowled the grass.
The money complicates things
The problem, of course, is the contract. Robert is owed $20 million for the 2026 season, with a 2027 club option that could keep him under control for another year. That’s not unreasonable for an elite defender with five-tool potential — but it’s a hefty sum for a player who’s struggled to stay healthy and consistent.
If the Yankees pursue a deal, they’d likely push for the White Sox to eat a portion of the salary. In that case, Robert could become a worthwhile upside play, a low-risk, high-reward move that gives the Yankees flexibility if he rebounds at the plate. Should he perform well, the team could keep him for 2027 at a manageable cost.
Balancing the future and the present
There’s also the question of how Robert fits into the Yankees’ long-term plans. Internal options like Jasson Dominguez and top prospect Spencer Jones are already knocking on the door, but both come with uncertainty. Dominguez just spent a season ceading reps to Grisham, and Jones has yet to prove himself at the big-league level.
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So, the Yankees face a crossroads. Do they double down on high-upside talent and spend more money, or do they give their young players a chance to grow? A trade for Robert would suggest a middle ground — one that gives them defensive stability now without fully blocking the future.
With a crowded outfield market and several moving parts, Brian Cashman’s next decision could shape the Yankees’ outfield for years to come. The question is whether they’re ready to bet on another talented, unpredictable player like Luis Robert Jr., or if they’ve learned to play things a little safer.