Boston fans find Bleacher Report’s “biggest regret” for the Red Sox to be incredibly accurate.

One of the slowest offseasons in recent memory is drawing to an end as Opening Day approaches. At last, a complete evaluation of off-season performances is possible.

This week, Bleacher Report released a list of every team’s greatest offseason regrets. Most teams are able to identify a single incident, such as missing out on a player, signing a player, or leaving a gap in a certain position on the roster.

Tim Kelly’s evaluation of the Boston Red Sox during the offseason is more comprehensive, yet it is still rather accurate. He thinks the Red Sox will be sorry for “not spending like the Red Sox.”

Over the past few seasons, Boston has been spending small-market money, and given the promises it made to fans, the front office’s business actions are nearly inexcusable. Even experts and insiders in MLB are baffled by the Red Sox’s recent decisions.

Kelly continues, “There’s virtually no way that the Red Sox’s starting pitching problems could have been resolved by just signing Lucas Giolito.” To be truly competitive in MLB’s “deepest division,” Boston would have required another elite arm. With Giolito out of the picture and all but one elite free agent signed, the Red Sox appear more desperate than ever.

The Red Sox’s biggest regret of 2024 will be not trying this offseason

They wouldn’t be in this situation, and this fourth year of their rebuild might be their last, had they paid up the cash for Jordan Montgomery or Blake Snell months ago. But the Red Sox will be confined to the cellar once more with just one legitimate starter in the rotation and little experience to guide the pitchers they already have.

Kelly at least pointed the finger of responsibility for Boston’s problems in the proper direction by criticizing ownership’s frugal spending. The Red Sox have suffered greatly ever since their historic run in 2018 and their huge payroll drop. It undoubtedly helps, even if ownership continues to swear that investing on talented players does not guarantee winning games. The dedication to a minimal payroll now verges on insanity.

In addition to being embarrassing, the Red Sox’s attempt to persuade the public that its ownership is doing its best is inconsistent with the team’s history of winning four World Series in less than 20 years. This is the third-most valuable team in Major League Baseball despite having the 12th-lowest payroll.

Red Sox Nation will know why if the 2024 Red Sox season performs as poorly as pundits and supporters predict it would.

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