The Chicago Cubs, like any club with postseason ambitions, are constantly searching for ways to improve around the edges of their roster. Contenders rarely stand pat. They look for incremental upgrades, insurance policies and depth pieces who can address weaknesses before they become real problems. That mindset explains why Chicago continues conversations with free agent pitcher Zac Gallen. It also helps explain why some fans have floated the idea of bringing back a familiar face to strengthen the bench.
After months of uncertainty surrounding his standing with the Philadelphia Phillies, the organization ultimately decided to cut ties with the 33 year old. Castellanos had signed a five year, 100 million dollar contract following the 2021 season, meaning the Phillies will absorb the final year of that deal. He is still owed 20 million dollars for 2026, and Philadelphia will be responsible for nearly all of it, leaving any new team to pay only the league minimum.
The split was not quiet. Castellanos acknowledged on social media that he brought a beer into the dugout after being removed from a game in Miami. He was benched the following day and reportedly confronted manager Rob Thompson and members of the coaching staff. Shortly after his release, The Athletic detailed the deterioration of the relationship, citing more than 12 players who were willing to speak about how things unraveled during the 2025 season. It was not a flattering portrait.
Still, for the sake of argument, set the off field drama aside and focus strictly on performance. Money is not the obstacle here. The question is whether Castellanos would help the 2026 Cubs.
Defensively, Castellanos has become a major liability. This is not a case of being merely below average. By most advanced metrics, he has ranked as the worst defensive outfielder in Major League Baseball. If Chicago were to add him, he would not be a realistic option in the field. That makes him a designated hitter only bat off the bench, which severely limits roster flexibility. The Cubs already plan to use Moises Ballesteros primarily in the DH role, so doubling down on another one dimensional player would further restrict lineup options.
Offensively, the peak years are well behind him. Castellanos was electric after the Cubs acquired him in 2019 and followed that up with a career year for the Cincinnati Reds in 2021, which led to his 100 million dollar deal. Since then, however, his production has settled into mediocrity. From 2022 through 2025, he has been exactly league average, posting a 100 wRC plus with a .260/.306/.426 slash line.
One counterargument is to deploy him strictly against left handed pitching. In theory, that platoon could pair with Ballesteros facing right handers. But even that niche value is shrinking.
Nick Castellanos vs. LHP (Since 2023)
2023: 187 PA, .930 OPS, 147 wRC+, 8 HR
2024: 170 PA, .830 OPS, 124 wRC+, 10 HR
2025: 188 PA, .680 OPS, 87 wRC+, 5 HR
The downward trend is unmistakable.
If the Cubs need right handed plate appearances against lefties from the DH spot in 2026, there is already a better in house option. Matt Shaw delivered a 125 wRC plus with six home runs in 110 plate appearances against left handed pitching last season. He offers more upside and far greater defensive versatility.
Castellanos had his moment on the North Side. But roster construction is about present value, not past memories. For a team aiming to contend, this is one reunion best left in the past.