As the NLCS continues on, it’s a painful reminder that the Philadelphia Phillies once again fell short of their lofty championship aspirations. Ahead of them now awaits the most crucial offseason of this contending core’s window with several key players hitting free agency.

Now more than ever, the team’s front office must hit on just about every decision they make to keep the franchise’s contention window open. Whiffing on those decisions could ultimately sabotage the team’s season, as these ones did to the 2025 team.

3 front office decisions that cost the Phillies in 2025

Signing Jordan Romano

The first regrettable decision is an obvious one that everybody can agree on. Having lost key relievers Jeff Hoffman and Carlos Estévez in free agency, president of baseball operations Dave Dombrowski had to strengthen the team’s bullpen somehow. He chose to bring former Toronto Blue Jays closer Jordan Romano in on a one-year, $8.5 million deal.

Romano’s Phillies tenure started with an Opening Day dud in which he blew a late eighth-inning lead with two earned runs allowed. That should’ve been a sign of things to come, as the veteran reliever’s 39 earned runs given up were nearly as much as his 42 2/3 innings pitched. The injury bug that caught Romano in 2024 found him again, but when healthy, he still finished with an 8.23 ERA that was enough to keep him off the postseason roster.

Signing Max Kepler

The Phillies’ only other significant free agent pickup of last offseason, Max Kepler was at least a little less disappointing than Romano. That’s not to say that he played well, however, as his .216/.300/.391 performance didn’t warrant the one-year, $10 million contract handed to him. Kepler seemed like an odd fit in Philadelphia from the start, given that he’s a left-handed bat in a lineup full of lefties and had never played left field at the MLB level.

Despite his 18 home runs ranking third on the team, Kepler never really got going in the red pinstripes. He deserves some credit for swallowing his pride and committing to manager Rob Thomson’s platoon plan, but Phillies fans certainly hope that the front office will fail to grant Kepler’s wish to return and upgrade their outfield situation next season with somebody else.

Not calling up Justin Crawford

Speaking of the Phillies’ 2026 outfield situation, Justin Crawford is the most important piece. The 21-year-old Crawford excelled with an unbelievable .334/.411/.452 slash for Triple-A Lehigh Valley this season. That earned Crawford some love from MLB Pipeline, with them ranking him as their No. 54 prospect on the Top 100 list.

Dombrowski had made it clear that no matter how well Crawford was hitting in the minors, he wouldn’t earn the call-up unless he was given the chance to play every day. Crawford should’ve been promoted to play in about June, when it was clear that outfielders Nick Castellanos and Kepler were struggling badly.

Crawford’s career .322 average across four seasons in the minors suggests that he has an above-average hit tool that could translate to the majors. Adding a shot of youth to the team could’ve helped an aging lineup which once again failed to produce in October. Crawford has a good shot to make the 2026 Opening Day roster as the Phillies’ starting center fielder as long as the right outfield moves are made this offseason.