{"id":516778,"date":"2026-01-12T15:12:16","date_gmt":"2026-01-12T15:12:16","guid":{"rendered":"https:\/\/www.rawchili.com\/mlb\/516778\/"},"modified":"2026-01-12T15:12:16","modified_gmt":"2026-01-12T15:12:16","slug":"the-red-sox-sad-day-this-weekend-was-nearly-a-year-in-the-making-and-threatens-to-happen-again","status":"publish","type":"post","link":"https:\/\/www.rawchili.com\/mlb\/516778\/","title":{"rendered":"The Red Sox\u2019 \u201csad day\u201d this weekend was nearly a year in the making \u2014 and threatens to happen again"},"content":{"rendered":"

I don\u2019t want to say I told you so \u2014 because I definitely wasn\u2019t alone in my worries about this whole situation, although I did take considerable heat for it on Twitter<\/a> \u2014 but let\u2019s just say that what unfolded this weekend with Alex Bregman is exactly what I figured would happen immediately following the Rafael Devers trade.<\/p>\n

Now, do I tend to forecast the future a little pessimistically? Yes. Despite that, this whole predicament seemed all but unavoidable, given Craig Breslow\u2019s track record and Boston\u2019s propensity to lose trades when they send their stars away to teams out west (or those in New York, too).<\/p>\n

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But even at the time of Bregman\u2019s signing, I wasn\u2019t happy with any of it. I\u2019m of the genuine belief that Bregman was never going to play second base<\/a>. I\u2019m not sure how clear that was to others, especially those within the Red Sox organization, but it seemed to me that it was always a bit of smoke and mirrors by Boston\u2019s public facing figures.<\/p>\n

A desperate overpay in January doesn\u2019t erase the fundamental dysfunction of an organization that creates its own holes just to struggle to fill them.<\/p>\n

No matter what their initial intentions were, it is now an indisputable fact that the Red Sox angered and subsequently traded away the heart of their offense for three productive months of 31-year-old Alex Bregman. That is an absolutely absurd outcome that shouldn\u2019t have been possible.<\/p>\n

But let\u2019s be clear about two things: Bregman\u2019s contract is an overpay for an aging used-to-be superstar. Also, his departure to Chicago should be fully blamed on this front office, not him. He\u2019s earned the right to find a nice city to close out his career and settle down with his family, and he should also do that while finding the best opportunity and compensation for him.<\/p>\n

Now, I am indubitably happy that the Red Sox did not match this contract and I truly haven\u2019t wanted to re-sign Bregman all offseason. But when you give up so much for one guy, you, of course, will be criticized when he decides to leave less than a year later.<\/p>\n

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I am positive that there will be people out there who defend the situation and say that Boston will make up for it by using the money on someone else, just as they did after the Devers dump. But even if the Red Sox bring in a comparable replacement (Bo Bichette, I, unlike others, would be delighted to have you in Boston<\/a>), this won\u2019t do anything to fix this overall problem.<\/p>\n

The Red Sox traded Devers to supposedly get his money off the books. They haven\u2019t done anything with it nearly seven months later. Boston didn\u2019t spend money on Bregman, but hey! They still have half an offseason to spend it elsewhere! But no matter what happens for the rest of this offseason, Boston\u2019s unwillingness to spend on free agents to improve the QUALITY and not just the MAKEUP of the team is a problem that will stand in the way of success. They are the only team in the league that hasn\u2019t made a free agent deal thus far, and while they\u2019ve made some promising trades to try and bolster this roster, their unwillingness to spend stands out.<\/p>\n

Signing Bo Bichette would be a fantastic move \u2014 he is exactly the kind of dynamic talent that this roster needs to replace Bregman (and on a larger level, Devers). But in the wake of the Bregman debacle, a $300 million check wouldn\u2019t feel like a bold pursuit for improvement, it would feel like a move the front office was forced into by a PR\/roster nightmare of its own making. It will be easy for leadership to take a victory lap and claim they were \u201caggressive\u201d all along, but we should know better by now. A desperate overpay in January doesn\u2019t erase the fundamental dysfunction of an organization that creates its own holes just to struggle to fill them. Whether it\u2019s refusing no-trade clauses or back-loading contracts with decades of deferrals, their approach has become a blueprint for near-misses and \u201csad days.\u201d<\/a> Until ownership prioritizes the quality of the roster over the makeup of the balance sheet, this isn\u2019t just a bad day in January \u2014 it\u2019s a preview of a saga that will play itself out again when we watch the next star walk away.<\/p>\n","protected":false},"excerpt":{"rendered":"I don\u2019t want to say I told you so \u2014 because I definitely wasn\u2019t alone in my worries…\n","protected":false},"author":2,"featured_media":516779,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":"","_share_on_mastodon":"0"},"categories":[2375],"tags":[72,5,88,141,48,2542,4,863,89,2543],"class_list":{"0":"post-516778","1":"post","2":"type-post","3":"status-publish","4":"format-standard","5":"has-post-thumbnail","7":"category-boston-red-sox","8":"tag-alex-bregman","9":"tag-baseball","10":"tag-bo-bichette","11":"tag-boston","12":"tag-boston-red-sox","13":"tag-bostonredsox","14":"tag-mlb","15":"tag-rafael-devers","16":"tag-red-sox","17":"tag-redsox"},"share_on_mastodon":{"url":"https:\/\/channels.im\/@mlb\/115882776487267382","error":""},"_links":{"self":[{"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/posts\/516778","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/comments?post=516778"}],"version-history":[{"count":0,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/posts\/516778\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/media\/516779"}],"wp:attachment":[{"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/media?parent=516778"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/categories?post=516778"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/tags?post=516778"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}