
The Pittsburgh Pirates entered this offseason with serious intentions about making a big splash. After being rebuked by one slugger, the Pirates should have shifted their focus from Kyle Schwarber to Pete Alonso. This potential pivot was a clear and missed opportunity to secure a franchise-altering slugger.
Now, with Alonso signing a massive deal elsewhere, the Pirates’ cautious approach is again left under a harsh spotlight, raising questions about the execution of their stated ambition. Their earlier aggressive pursuit of another star proved they had the blueprint, but they failed to secure the player who could have transformed their lineup.
BREAKING: First baseman Pete Alonso and the Baltimore Orioles are finalizing a five-year, $155 million contract, sources tell ESPN. Alonso leaves the Mets to make a loaded AL East even better.
— Jeff Passan (@JeffPassan) December 10, 2025
The Pirates' initial aggressive pursuit of Schwarber had signaled a potential shift in organizational philosophy. For a club historically hesitant to engage in the deep waters of free agency, their substantial offer was a notable step. Schwarber re-signed with the Phillies for 5 years and $150 million. At the time, Ken Rosenthal of The Athletic reported that the Pirates offered 4 years and around $120 million – about the same average annual value as the Phillies offer.
This report confirmed the front office was prepared to commit major dollars for elite power. It did seem as if the Pirates were willing to spend some serious cash on a slugger – so why didn't they offer a similar contract to Alonso? In retrospect, that may be the defining question of their offseason.
While the Pirates hesitated, the Baltimore Orioles acted. Alonso, the premier right-handed power bat on the market, signed with the Orioles for 5 years and $155 million. This deal showcases the exact market the Pirates were prepared to enter. The Mets were reportedly reluctant to offer Alonso more than three years, which was precisely where an aggressive suitor like the Pirates could have stepped in with a decisive fourth or fifth year. And if it took five years – why not?
The Orioles answered that question affirmatively, securing the slugger with the commitment the Pirates had already modeled for Schwarber. Pittsburgh’s failure to pivot with similar vigor has now left them empty-handed.
The baseball fit for Pittsburgh was nearly seamless, which makes the outcome all the more frustrating for fans. Alonso has similar power output to Schwarber, just from the right-handed side of the plate instead of the left. According to Statcast, PNC Park and Citi Field have almost the same park factor, so there probably wouldn't have been a major dip in his power.
Alonso would immediately have been the Pirates’ most feared hitter. Considering that the Pirates have six prospects on MLB Pipeline's Top 100 list, you could also envision him being a locker room leader for a team that is going to have an influx of young talent in the next few years. Instead, that transformative presence and protection for players like Bryan Reynolds and Oneil Cruz will now benefit the Orioles in the American League.
Need another reason to like Paul Skenes? He recently approached Ben Cherington and volunteered to pitch free agent targets on playing in Pittsburgh. My story: https://t.co/2T6rGotJHt
— Jason Mackey (@JMackeyPG) December 9, 2025
The Orioles' decisive action shows what genuine contender aggression looks like. In retrospect, the Pirates’ offseason is defined by a "what if." They demonstrated a theoretical willingness to spend but lacked the adaptive, relentless pursuit required to actually land a franchise cornerstone. As Alonso prepares to unleash his home run power in Baltimore, the Pirates are left to wonder how different their future could have looked had they simply redirected their Schwarber-level offer to the right target.
The path forward was clear, but the Pirates stopped short. They should have been doing whatever it took to meet with Alonso – even if it meant getting Paul Skenes on the phone with him – and not left the room until they made a compelling case to bring the Polar Bear to Pittsburgh.
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