Time Machine: "Back to October 18th, 2021"...
The Boston Red Sox were taking on the Houston Astros at Game 3 of the ALCS at Fenway Park. Kyle Schwarber had just hit a towering grand slam to right field, and Hunter Renfroe made a sliding catch to end the game. In such a dominating fashion, the Red Sox were up 2-1 in the series.
The next night, Nick Pivetta was pitching amazingly, and Xander Bogaerts gave the Red Sox a 2-1 lead with a towering two-run home run over the monster off Zack Greinke. However, stud rookie pitcher Garrett Whitlock gave up a game-tying home run to Jose Altuve, and the Astros never looked back. Jason Castro hit the game-winning double, with more runs being scored in the 9th inning as the Astros tied the series up 2-2.
Afterwards, the Red Sox completely fell apart and lost two straight, getting shut out in the latter Game 6 and thus, eliminating them from the playoffs.
Red Sox Still Recovering From 2021 Playoff Meltdown
Now, to think that this one miraculous playoff run was a sign of things to come, it was the right thinking at the time. The Red Sox had a 92-win season and rebounded after a disastrous 2020 and trading off two of their former 2018 stars, among others. However, things would never be the same.
The problem was that the 2021 Red Sox had given false validation to a flawed roster. Some forget that they were carried by an unsustainable offensive explosion (consisting of Kiké Hernandez, Kyle Schwarber, J.D. Martinez, Rafael Devers, and Xander Bogaerts) and a patchwork rotation that overperformed (Nick Pivetta, Eduardo Rodriguez, and Garrett Richards).
That hot streak after eliminating the division-winning Tampa Bay Rays and going 6 games deep into the ALCS, the front office was deluded into thinking they were closer to a World Series title than they were. It blurred the lines of what should've happened: Retooling the roster.
If Dave Dombrowski were still head of baseball ops, he would've had a field day. However, it was Chaim Bloom in that chair, and things were operated differently. It almost made him forget about trading away Mookie Betts, which is who they truly needed in 2021. This made him believe that what he was doing was correct and everything was going to work out.
Spoiler: It didn't.
With this, the front office grew confident in what Bloom was doing, and they decided to take a hands-off "thread-the-needle" approach with Bloom operating everything behind the scenes. They walked the line as they let Kyle Schwarber AND E-Rod leave in 2021. The next season, the Red Sox had four stars on expiring contracts: Xander Bogaerts, Nathan Eovaldi, Christian Vazquez, and J.D. Martinez.
As for Martinez, he had regressed in 2022, so letting him go at the end of the year was the right move. The Red Sox had a 20-win June, but fell hard in July, suffering an 8-19 record in that month.
At the deadline, the Red Sox were rumored in selling. They did with Christian Vazquez and got a great return for him (RF Wilyer Abreu and IF Enmanuel Valdez), but they proceeded to do nothing else. Worst of all, they never extended Bogaerts or Eovaldi during the season, and let them walk for nothing at the end of the season. They could've gotten a much better farm system if they traded those two at the deadline, but proceeded to keep them.
The truth was, after 2022, the team lacked a cohesive vision. They weren't selling and they weren't buying for a championship, just testing the waters and hoping things would work out.
Spoiler: It didn't.
Jeter Downs was the headliner of the Mookie Betts trade, but was DFA'd by the organization the very offseason after he made his major league debut. Bobby Dalbec (while a Dombrowski draftee) didn't pan out either. They signed a big contract with Trevor Story in free agency for six years, $140 million. To say that he's been an injury-riddled mess is quite an understatement.
The next year, they signed Japanese sensation Masataka Yoshida to a five-year deal worth $90 million. He's also an injury-riddled mess with consistency issues. Kiké Hernandez showed that his 2021 season was a mirage, coming back to his true form as an inconsistent utility player, and was traded back to the Dodgers in 2023. Also in 2023, former Red Sox pitcher Nathan Eovaldi signed with the Texas Rangers. In his first season, he helped them win the World Series.
The Red Sox fired Chaim Bloom in 2023, and Craig Breslow took over operations. Under his belt, they traded Chris Sale to the Atlanta Braves for IF Vaughn Grissom. It didn't seem lopsided at the time, as Sale was dealing with injuries and was on a huge salary. But after 2024, Sale won the Cy Young Award for the National League, proving he still has more left in the tank. Alex Verdugo (second player acquired from the Mookie trade) was traded to the Yankees, and they made the World Series in 2024.
As for Breslow himself, he was just like Theo Epstein: an analytics and pitching guru who was focused on winning a championship. He even promised it on the day of his press conference, which was very bold of him. Unfortunately, it was a whistleblower rather than anything else. Ever since he took the job, Breslow has never helped the Red Sox win a World Series.
He's kept most of the staff (especially ones who have won with the team in past years, all the way back in 2004) out of the loop in operations and created havoc in the locker room after signing Alex Bregman to a three-year deal. Thus, the Rafael Devers drama within the organization started, leading up to his eventual shocking trade to the San Francisco Giants.
The 2021 Red Sox were never supposed to be a contender. They were a scrappy, overachieving team in the middle of a soft rebuild. But when they surprisingly surged to the ALCS, when a Schwarbomb shook Fenway Park, when Hernandez was hitting everything in sight, when Bogaerts launched that 2-run home run, it was when fans believed again, but it changed everything.
That playoff run wasn't a foundation. It was a mirage, an illusion that convinced the front office and fans that the Red Sox were ahead of schedule and that Bloom was doing an amazing job and knew what he was doing. Instead of committing to a rebuild or going all-in, they did neither. They hesitated and cut corners. They let stars walk and failed to invest in a true core.
Because of all that, the team unraveled on the field. The Red Sox didn't lose their way overnight. They lost it the moment they believed that 2021 was real. In the end, that miracle run didn't launch a new era of contention; it delayed the hard decisions. It justified the wrong ones, and it gave hope when there should have been humility towards the situation. Now, in 2025, the bill has come due. They made a deal with the devil for that playoff run, and now all their stars are gone, and most importantly, searching for a new identity.