The "what if" game is a very dangerous one to play when it comes to baseball. The butterfly effect is real with personnel decisions, as even the smallest trade from a few years ago can influence an organization's thinking today.
Nevertheless, the Boston Red Sox have put us in a situation where it's basically impossible not to ask "what if?" about a myriad of choices. The Mookie Betts trade, the Rafael Devers saga, Alex Bregman's free agency tour, and Chris Sale's renaissance in Atlanta merely scratch the surface of what has been an emotional rollercoaster since 2018.
Let's narrow our focus to just one situation for now: the great shortstop migration of 2022. That calendar year, the Red Sox paired Trevor Story and Xander Bogaerts for one glorious season (even if the team as a whole stunk) before ultimately plugging the former in for the latter, whom they lost in free agency to a massive contract with the San Diego Padres.
We're now four years into this new Bogaerts-less world, and it's becoming clearer by the day that the Red Sox chose wrong.
Xander Bogaerts hasn't been worth the money ... but he's still been better than Trevor Story - which means the Red Sox opted to sign a cheaper and lesser player, though they could have had Bogaerts for the same price if they had acted earlier. And they might have avoided the… pic.twitter.com/ddtNpvdsp8
— Tony Massarotti (@TonyMassarotti) May 12, 2026
Red Sox stuck themselves between a rock and a hard place with Trevor Story's contract
This conversation requires a lot of nuance, which isn't exactly the kind of treatment Story has gotten in Boston in recent years. He did finally stay healthy enough to produce at an All-Star-caliber level in 2025, but pretty much everything else he's done since 2022 suggests that he's far removed from his peak with the Colorado Rockies.
That being said, his contract (six years, $140 million) pays out literally half of the total that Bogaerts' does. That price point was insane from the moment the Friars offered it, and there was never a world in which the Red Sox were going to pay him, Story, and Rafael Devers more than $700 million combined.
It was nice having Story finally lock down second base during that 2022 season, and that trio of infielders would have been a good start for Craig Breslow to build around. But the Red Sox really lost Bogaerts years before he reached free agency, when they could have gotten him to sign a sub-$200 million extension that would have been far more palatable.
Bogaerts is having his own renaissance this year with the Padres, but his contract is and will be an albatross for years to come. At least the Red Sox only have to pay Story through 2027, at which point they can decline his $25 million club option for 2028.
Is that a silver lining worth caring about during a lost season? Perhaps not, but silver linings are all the Red Sox are giving us to work with this year.
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