Welcome back to the Mayor’s Office, our weekly series in which Jake Wallinger sends one naughty member of Red Sox Nation to Mayor Michelle Wu’s office for discipline, public shaming, and penance as we all strive to build a stronger baseball team and city.
This week, it’s a gone but definitely not forgotten CBO who is in an Uber to Government Center.
Designated Hitter Masataka Yoshida continues to be a complete disaster for the Red Sox. So much so that I came very close to just posting last week’s Mayor’s
Office again for this week’s edition. But I have integrity (and also I’m not allowed to do that). Instead, I figured out that I could come at the same topic from a bit of a different angle.
The angle I want to tackle “The Masataka Yoshida Problem” from is that of former Boston Red Sox Chief Baseball Officer Chaim Bloom and a series of catastrophic decisions in 2022 that are still affecting the Red Sox today (and likely also 2026… and 2027).
The 2021 Red Sox gave New England a magical, unexpected ride to the American League Championship Series. After a catastrophic year on and off the field prior, the ‘21 Sox were a breath of fresh air. But fresh air doesn’t win championships. When the dust finally settled after the team’s elimination at the hands of the Houston Astros, there were decisions to be made.
The first decision was actually not one to be made by Bloom, but by the Red Sox’ Designated Hitter of four years, JD Martinez. Martinez decided to opt-in to the final year of his five-year/$110 million deal signed in the spring of 2018, setting off a chain reaction that the team is still reeling from.
If trade deadline acquisition Kyle Schwarber wasn’t the highlight of the 2021 season, he undoubtedly was on the shortlist. After coming over from the Washington Nationals, Schwarber slashed a dazzling .291/.435/.522 in 41 games for the Sox while splitting time between left field, first base, and DH. In the postseason, Schwarber was admittedly more pedestrian, managing only a .718 OPS. However, he did swat three home runs in that time (one in each round), with his grand slam in game 3 of the ALCS becoming a fan-favorite moment.
Many Red Sox fans saw Schwarber’s effect on the team in the second half of ‘21 and were eager for the team to negotiate with the free-agent-to-be. Red Sox Nation wanted Kyle Schwarber to call Fenway Park home for years to come. However, the aforementioned opting-in of JD Martinez complicated things. Schwarber, to put it lightly, is not a gifted defender. That’s fine, not everyone is. But with Martinez (also a very poor defender) occupying the DH spot in ‘22, it became complicated to envision Schwarber fitting on the roster without greatly sacrificing defense.
But, did it really? For a good chunk of his Red Sox tenure, Schwarber played (an admittedly mediocre) first base. Why couldn’t the team just play him there for a year and then slot him in at DH once Martinez walked at the end of the season? The team’s first basemen for most of ‘21, resident heartthrob Bobby Dalbec, had shown only flashes of being a consistent major-league hitter. This, coupled with his sub-par defense at first, makes the team’s insistence on rolling with Dalbec (who posted a paltry .599 OPS in his next and final 500 plate appearances with the Red Sox), completely bizarre.
The winter came and went, and Kyle Schwarber signed with the Philadelphia Phillies and old friend Dave Dombrowski for 4 years/$79 million. Since then, he has only .226/.349/.504 with 180 home runs INCLUDING 4 LAST NIGHT. Oh well! But here’s the kicker. Just nine months after Schwarber signed with the Phillies, the Red Sox inked Japanese outfielder (DH if we’re being honest) Masataka Yoshida to a 5 year/$90 million deal.
I won’t go into the nasty details regarding Yoshida’s disastrous Red Sox tenure, that’s what last week’s Mayor’s Office was for, but it’s bad! It’s made even worse when compared to Schwarber, who somehow, someway, received less money than Yoshida! Maybe Bloom was trying to make up for the Schwarber miss. Maybe he just wanted to spend some cash. Maybe he meant to sign someone else! Either way, this series of events left the 2025 Red Sox with a black hole of ground balls to second slotted in at designated hitter every night. And that black hole has two more years left on his deal!
Mr. Bloom, Mayor Wu will see you now.
