The Yankees took a risk when they kept a struggling outfielder on a lower salary this season. That player, who agreed to a $5 million contract after three years of batting below.200, became one of the most sought-after free agents on the market. Now, as the Bronx watches helplessly, their project to reclaim land seems to be heading straight for their crosstown rivals.

One of the most interesting things to happen in this free agent class is Trent Grisham’s turnaround. The two-time Gold Glove center fielder was such a letdown before this season that he agreed to a pay cut, which is very rare for an arbitration-eligible player. His pay went down from $5.5 million in 2024 to $5 million this year, which is very rare in baseball’s arbitration system. Even though Cody Bellinger had a terrible .542 OPS and negative-1.6 bWAR in 2021, he still got a $900,000 raise because arbitration usually gives players’ money, no matter how well they play.

The Bronx rivals Mets, had a tough 2025 season in center field, going through the Jose Siri and Tyrone Taylor platoon without ever finding a good fit. They thought getting Cedric Ullins from Baltimore would help, but he kept up his four-month slump in Queens. Grisham’s big game makes him an interesting option for the other team in the city. He hit 33 home runs, drove in 74 runs, scored 87 runs, and got 116 hits in 143 games, all of which were career highs. A player who had only hit 15 home runs in a season before this one made a huge jump with these 33 home runs.

Brandon Nimmo is in left field, and Juan Soto is in right field. The team sees Grisham as the missing piece in their outfield puzzle. Jeff McNeil is currently playing center field, but the team seems ready to make a change, even though top prospects Carson Benge and Jett Williams are working their way up through Triple-A Syracuse.

According to Spotrac, Grisham’s projected contract would pay him $12.1 million a year for four years. This is a big jump from the $5 million he made with the Yankees. The Mets might have a problem with too many prospects waiting for chances, but after their center field problems, they seem willing to deal with it. The Yankees could be even more upset that Grisham is going to their biggest rivals because they will see a player they developed reach his full potential in Queens.

The Grisham situation hurts, but it’s not the only problem the organization is having. The New York Yankees have a lot of holes to fill on their roster and tough choices to make as they try to build a team that can win the World Series.

Yankees face bigger problems beyond Grisham’s departure

The New York Yankees have a lot of problems to deal with this offseason, and losing Grisham is just one of them. The Blue Jays knocked them out of the playoffs, ending their season on a low note and extending their World Series drought. The front office now has to quickly put together a new roster because the old one didn’t meet championship expectations.

The bullpen is a very important area that needs to be fixed right away. Devin Williams, who was traded to the Yankees with high hopes of being a superstar closer, had his worst game in a Yankees uniform. Even though David Bednar joined the team in the middle of the season, the back end of the bullpen was still weak because the two-time All-Star was having trouble. Christopher Kline from FanSided has suggested Emmanuel Clase from Cleveland as a solution. He suggested that the Guardians get prospects Bryce Cunningham, T.J. Rumfield, and Brendan Jones in a trade.

Clase has a lot of experience that will help him in any negotiation. The right-handed pitcher was chosen for the All-Star Game three times in a row and led all of baseball in saves in 2022 and 2023. His career ERA is a great 1.88, and his contract lasts until 2026, which gives him stability right away. He could take over as the closer, moving Bednar into a high-leverage setup role. This would make a strong late-inning duo.

But there are big problems that make any deal harder. Since July, Clase has been on paid leave because of an ongoing gambling investigation. There is no clear timeline for when the investigation will end or when he will return to work. It’s very risky to trade three prospects for a player whose availability is still up in the air, and any deal would have to wait until he was cleared to play again.