The Philadelphia Phillies enter a make-or-break offseason for the franchise.

With an aging core, time is running out for this group. The window could close at any moment, given how many players are already in their mid-30s. That puts a lot of pressure on President of Baseball Operations, Dave Dombrowski, to get the job done and upgrade this roster so they can make one last run at a World Series together.

Several areas of the roster need to be upgraded. The lineup could use more power, but manager Don Mattingly has already made it known he would like the team to play closer to how they did in August, drawing walks and passing the baton, rather than waiting for a single big blow via the home run.

On the pitching staff, depth needs to be built up in the starting rotation. The Phillies are set with Cristopher Sanchez, Jesus Luzardo, Zack Wheeler, Aaron Nola and Andrew Painter, but there is nothing behind them. Also, the bullpen needs help, especially from the left side, after another meltdown.

Phillies need to keep roster clean for up-and-coming youngsters

However, there is one free-agent mistake that the team must avoid at all costs this winter: not blocking their young players from having runway in the Major Leagues. Namely, Aidan Miller and, soon after, Bryan Rincon, but also Justin Crawford, who is already a fixture in the Big League lineup.

Philadelphia needs to infuse some youth into their lineup to help extend the window of this current core. The fastest way that could be undone is signing players to lucrative, long-term deals in free agency who look like they can help the team immediately, but present roadblocks down the road.

Miller, the top position player prospect in the organization and a top-100-ranked player in baseball, was going to be in the team’s plans for 2026 before a nagging back injury knocked him out for spring training.

The injury was worse than anticipated, as the young infielder missed virtually the entire season, coming back to the field in the final days. Participating in the Arizona Fall League, he looks healthy and poised to make an impact in the Major Leagues.

A shortstop right now, Miller also profiles well as a third baseman if need be. That move could occur because Rincon is an elite defensive prospect at shortstop who is beginning to show some development with the bat.

Phillies will count on Aidan Miller, Bryan Rincon and Justin Crawford

He may not be in the mix for a Big League spot in 2027, but there are youngsters who surprise every offseason and in spring training, earning a spot with incredible production. Rincon made strides in every area the team wanted him to in 2026, setting up a potential breakout in 2027.

Crawford didn’t have the best rookie season with the Phillies, but the tools are there for him to become a productive Big Leaguer. Philadelphia could deploy him in a platoon in 2027, but they need to keep giving him playing time to realize his potential.

What Chandler Simpson has done with the Tampa Bay Rays is proof that a player with Crawford’s skill set can be productive at the highest level. Maybe a move to a corner outfield spot could help him settle in, much as it did for Simpson, who turned himself into a Gold Glove finalist in one year after a rocky 2025 in the field.

Philadelphia has to get him in a position to take more advantage of the game-changing speed that Crawford possesses.