A year ago, around this time, John Henry, the owner of the Boston Red Sox, had a picture posted of him smoking a cigar. He seemed very smug, self-aggrandizing, and proud of his accomplishments.
He had just acquired free agent Alex Bregman. It was a 3yr/$120M deal (in reality, it was a 1yr/$40M deal with deferments and two player opt-outs). It culminated in an offseason of trading for Garrett Crochet and signing closer Aroldis Chapman. It was a good offseason.
As good as last season’s offseason was, this offseason has been equally bad…or worse. This offseason can’t be discussed without discussing the 2025 season. Due mainly to the Bregman signing, Rafael Devers turned into a malcontent, yapping his way out of town…traded to the San Francisco Giants.
I’m not 100% sure Henry didn’t view the trade as a blessing, shedding hundreds of millions in Devers’ contract. Management said it would be an addition by subtraction and that it would reinvest the Devers’ money. Half was true. It can’t be argued that the team performed better without Devers. They had a better record after he left, and they made the playoffs.
But here we are, in the middle of January, and the team has not reimbursed him. In fact, at the moment, the Boston Red Sox are the ONLY team that has not signed a free agent this offseason. They hold that distinction, since the Colorado Rockies finally got out of the slump and signed Michael Lorenzen.
The days of the Sox being the No.1 spending team in the league are long behind them. They haven’t been no.1 in payroll since 2019. And they don’t even sniff the top five anymore…they have been outside the top 10 the last three seasons, and 2026 looks like it will be four in a row. Who knows, maybe Henry is hurting for money; he just sold the Pittsburgh Penguins?
Whatever the reason, there is a different business model at Fenway Park. Recently, reports indicated the Sox made a significant offer for Bregman. And, for his part, there were reports that he wanted to stay with the Red Sox. So what happened? The rhetoric didn’t match reality, and Bregman is now a Cub.
Late Saturday, Bregman signed a 5-year, $175 M deal. Other details aren’t important. The only detail that matters is that whatever the Red Sox offered Bregman wasn’t good enough. And at the moment, the Sox are without a bona fide MLB third baseman. Devers is in San Francisco, and Bregman is now in Chicago. They have 23yr old Marcello Meyer, coming off a wrist injury, who could man the hot corner. He played a whopping 39 games at third base last year.
As far as remaining free agents, they could pivot to either Bo Bichette or Eugenio Suarez. But there are just no indications that this team, this year, is willing to dip its toes into free agency at all. They made no effort on Pete Alonso, and his price tag was only 5 yrs/$155M. Bregman now went for 5yrs/$175M. Bichette will surely cost more. At age 34, Suarez will cost less, but I won’t hold my breath that the Sox will even pursue him. They didn’t even re-sign free agent Rob Refsnyder.
They effectively replaced free agent Lucas Giolito with trade acquisition Sonny Gray, which is a wash at best. They also traded for Johan Oviedo. And to round out their pitching staff, they have last year’s free agent, Patrick Sandoval. Their biggest acquisition this offseason has been the trade for first baseman Willson Contreras, who will cost them $35M over the next two seasons.
So it’s not like they aren’t spending any money, but this feels like just rearranging the deck chairs on the Titanic at this point. This team is markedly worse than last season. And if we compare them to the rest of the AL East, it’s even worse.
The Blue Jays are the defending AL World Series representatives and have improved in the offseason. The Yankees were better last year, and have Gerrit Cole coming back. And the Orioles have been spending money, most notably on Pete Alonso. And the Rays are the Rays, always pesky with a chance, playing their brand of baseball. At the moment, the Red Sox aren’t a playoff team.
I ask again, Mr. Henry: where is the photo of you puffing on a celebratory cigar?
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