Red Sox top list of five most disappointing offseasons so far

The offseason isn’t finished, of course. Trades can still happen, and there are free agents who have yet to find their new home (or return to their old one). But the top players on the “Best Available Free Agents” list, guys like Jean Segura and Nathan Eovaldi, are not the ones who cracked many top 10 lists at the start of the offseason. 

Fans of some franchises are very happy. Yankees fans couldn’t have asked for much more, with Aaron Judge and Anthony Rizzo back and ace Carlos Rodon in the fold. Phillies fans saw their favorite team land the perfect free-agent fit in Trea Turner, and Rangers fans get to watch Jacob deGrom in their favorite uniform. 

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But for every happy fan base, there is one experiencing a terrible, horrible, no good, very bad offseason of what-might-have-been wishes and runner-up dreams. Let’s take a look at five of those clubs. 

Red Sox

The worst part of Boston’s frustrating — or, as many in Boston would say, infuriating — offseason for Red Sox fans isn’t the moves that have or have not been made, it’s the writing that’s pretty clearly on the wall: The front office does not seem committed to do what it takes to keep Rafael Devers in a Red Sox uniform beyond the 2023 season. They consistently low-balled fan favorite — and perennial All-Star and down-ballot MVP candidate — Xander Bogaerts from the beginning of potential extension talks right to the very end, then by all accounts overpaid Masataka Yoshida, an outfielder from Japan.

Devers is eligible to become a free agent after the 2023 season, entering his Age 27 season, and if healthy will certainly command a contract worth north of $300 million, probably closer to $350 million, at least. Unless there’s a dramatic change in approach, it’s hard to imagine the Red Sox even being competitive for his services. And it’s not that they can’t, it’s that they won’t. And that’s the infuriating part. At the moment, this is a roster that is worse than it was in September and the club seems destined for a second consecutive last-place finish in the AL East. Things are not good in Boston. 

White Sox

White Sox fans are not happy, folks. The club suffered through a mildly disastrous 2022 season, and this offseason has not been much better. In some ways, it’s worse because it sets 2023 up for more of the same (albeit with a new manager). The Sox let beloved first baseman Jose Abreu leave for the Astros, and the biggest bat they’ve acquired so far this offseason, Andrew Benintendi, hit exactly five home runs in 521 plate appearances last year.

They let rotation savior Johnny Cueto leave — technically, he’s still available as a free agent, but he’s not returning to the White Sox — and gave his rotation spot to Mike Clevinger, who missed all of 2021 and posted a 4.97 FIP in 23 games (22 starts) last season for the Padres, who were not interested in retaining him despite potential pitching staff needs. There’s been a lot of talk about the kind of improvements the club needs, but very little action. 


The Dodgers have been oddly quiet this offseason. Not only did they not land any of the premier free-agent stars, even though there was reportedly interest, but they lost one of their own, when Trea Turner signed with the Phillies. Unlike the other teams on this list, the Dodgers are pretty much guaranteed to make the postseason in 2023, and they’re the favorites in their division, too. But Dodgers fans have become accustomed to seeing upgrades every offseason, and this one hasn’t lived up to that standard. 


The Orioles were baseball’s best out-of-nowhere story last year — from 52 wins in 2021 to 83 in 2022 — and no doubt fans hoped the front office would continue 2022’s momentum by signing at least a few key free agents to add upgrades to a roster that outperformed, by wins and losses, most statistical measures. And that certainly seemed reasonable, considering the club basically hasn’t spent any real money on salaries the past few years. From 2016 to 2018, Baltimore’s average Opening Day payroll was right around $153.5 million, but in 2021-22, that average was $50.4 million.

The Orioles were connected, at least through reports and whispers, to several free agents who would have represented positional improvements. Instead, mostly crickets. They brought in starting pitcher Kyle Gibson on a one-year, $10 million deal — a smart move, but not a signature one — and gave bounce-back candidate Adam Frazier a chance to revive his career after bottoming out with the Padres and Mariners the past two seasons. There were clear areas where the Orioles could have spent to upgrade the roster, but that didn’t happen. And it’s not because there isn’t money — it’s because the Orioles chose not to spent the money they have. 

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The Twins wanted to bring back Carlos Correa, and they were, by most reports, the team that was most aggressive with early conversations and offers. But Correa was never going to offer any type of hometown discounts, and the Twins didn’t make the best overall offer, so Correa signed with the Giants. And they didn’t land the other shortstop who was still available on the market, Dansby Swanson, as he signed with the Cubs. But that might wind up not being such a bad thing in the long run.

The Christian Vazquez signing at catcher was a smart move, a three-year deal that will go a long way toward helping the pitching staff while providing some offense behind the plate. But the Twins came into the offseason hoping to upgrade at shortstop and in the rotation, and despite being relatively aggressive on both fronts, they’re still looking to solve those same issues. 

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