As the NLCS moves forward, Phillies fans are left with a painful reminder that Philadelphia once again came up short of their championship expectations. Now the franchise heads into the most important offseason of this core’s competitive window, with several key players set to hit free agency.
More than ever, the front office must nail nearly every decision to keep the contention window open. One wrong move could derail the entire season—just like the missteps that ultimately doomed the 2025 team.
3 front office decisions that cost the Phillies in 2025
Signing Jordan Romano
The first misstep is an easy one to point out. After losing key relievers Jeff Hoffman and Carlos Estévez in free agency, president of baseball operations Dave Dombrowski needed to reinforce the bullpen. His solution was signing former Blue Jays closer Jordan Romano to a one-year, $8.5 million deal.
Romano’s time in Philadelphia got off to a disastrous start when he blew a late eighth-inning lead on Opening Day. Unfortunately, that outing foreshadowed what was to come. He allowed 39 earned runs in just 42 2/3 innings, nearly a run per inning. Injuries once again plagued him—just as they did in 2024—but even when healthy, he struggled mightily and finished with an alarming 8.23 ERA. His performance was poor enough that he was left off the postseason roster entirely.
Signing Max Kepler
The Phillies’ only other notable free-agent signing, Max Kepler, was slightly better than Romano—but still a disappointment overall. His .216/.300/.391 slash line didn’t come close to justifying the one-year, $10 million contract. From the beginning, he seemed like an awkward fit: another left-handed bat in a lineup already crowded with lefties, and no prior experience in left field at the MLB level.
Kepler did hit 18 home runs—third-most on the team—and deserves some credit for buying into Rob Thomson’s platoon strategy. Still, he never found any real rhythm in Philadelphia. Fans are now hoping the front office moves on and upgrades the outfield rather than honoring Kepler’s expressed desire to return.
Not calling up Justin Crawford
Looking ahead to 2026, Justin Crawford is the most intriguing piece of the Phillies’ outfield puzzle. The 21-year-old dominated Triple-A Lehigh Valley, slashing an incredible .334/.411/.452 and earning the No. 54 spot on MLB Pipeline’s Top 100 prospects list.
Dombrowski insisted that Crawford would only be promoted if he could play every day. But when Nick Castellanos and Kepler were both struggling badly around June, that opportunity was sitting right in front of them. Crawford’s career .322 average in the minors suggests he has a plus hit tool that could translate immediately at the MLB level.
Injecting youth and athleticism into an aging lineup—one that once again disappeared in October—could have made a real difference. Now, Crawford has a strong chance to make the 2026 Opening Day roster as the starting center fielder, assuming the front office makes the right moves this offseason.