Castellanos has been a key piece of the Phillies’ roster since joining it in 2022. However, he is one of many players that Philadelphia could decide to move on from this winter. The outfielder fell out of the starting lineup in the postseason, leading many to ask when he will be traded, not if. Despite his shortcomings, he will have plenty of suitors on the trade market.

Both the Yankees and Phillies saw their seasons come to disappointing ends. Each contender lost 3-1 in the Divisional Series to teams that simply overpowered them. Despite the losses, though, both New York and Philadelphia figure to be back in the inner circle of contenders heading into the 2026 regular season. However, there is a lot of pressure on each front office to make moves.

Castellanos’ time with the Phillies is rapidly coming to an end. Bryce Harper wants Philadelphia to do everything it can to retain J.T. Realmuto and Kyle Schwarber this winter. In order to do that, the team will have to sacrifice elsewhere, likely by moving off of Castellanos’ bloated contract. The Yankees are one of few teams able to absorb one of the league’s more questionable contracts.

The Phillies will not get as much for Castellanos as they want. However, the outfielder could still fetch a good price. Here is what the Yankees could offer.

Phillies get: SP Brendan Beck, OF Trent Grisham

Yankees get: OF Nick Castellanos

Why should the New York Yankees trade for Castellanos?

Bellinger will have plenty of suitors in free agency when it kicks off after the season ends. Cashman and New York would love to hold on to him on a reasonable contract, but nothing is guaranteed. The Yankees cannot afford to have a big drop-off in production from that part of the field. Because of that, Castellanos is a great fit in New York’s lineup, even if it’s for a short time.

Castellanos has hit .250 or better in each of the last five seasons of his career. 2025 was a down year for the former All-Star, but he has what it takes to rebound and provide even more power to the Yankees lineup. The righty is a major downgrade defensively, but New York could use him as a designated hitter, splitting his time with Giancarlo Stanton in both spots in the lineup.

Left field is the last piece of the puzzle for both New York and Philadelphia to fill out. Each team lost their ace pitcher in 2025 and paid the price in the postseason. Despite disappointing ends to successful campaigns, neither team is giving up on their championship window. Castellanos’ contract isn’t pretty, but it is the price of competing for championships in New York.

Why should the Philadelphia Phillies trade Castellanos away?

To put things simply, Castellanos is no longer an essential piece of the Phillies’ plans. When he walked through the door in 2022, Philadelphia thought it had a “Big Five” with him, Harper, Realmuto, Schwarber, and Trea Turner. A few seasons later, the outfielder cannot stay on the field in the biggest spots. At this point, the veteran no longer has the cache that he used to.

Castellanos finished the season worrying fans with his attitude. The Phillies stumbled down the stretch, failing to push the Milwaukee Brewers for the top seed in the NL postseason. While it was not completely on him, Castellanos rubbed some people the wrong way before the playoffs started. His production was not good enough to overshadow his drama off the field.

The offseason is a time for tough decisions. Teams can’t win a championship in the winter, but they can easily lose one. The Phillies have their list of priorities ahead of free agency, and trading Castellanos might be at the top of it. Philadelphia has plenty of young talent to promote into his spot, and trading him would relieve the team of the questionable moments he causes.

Castellanos is a double-edged sword. However, it is a risk that the Yankees need to make at the right price. If the Phillies can come to a compromise with the AL powerhouse, the trade could be a win-win deal for all parties involved.