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    Red Sox Losing Alex Bregman Is A Disaster of Their Own Making

    How the Red Sox lost Rafael Devers, Alex Bregman, and their credibility in one stunning collapse.

    Jack Lindsay
    Image courtesy of © Gregory Fisher-Imagn Images

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    Another domino in the Rafael Devers saga has fallen. Alex Bregman has signed with the Cubs for five years and $175 million, with a full no-trade clause to boot.

    What an unmitigated disaster. 

    Now, this incident on its own is not the problem. Alex Bregman is on the older side, and $35 million per year is a steep price to pay for a player with production that will inevitably decline at a continually steeper rate. Yes, I have said previously that the Red Sox need to reconsider their approach to free agency, and I stand by that. Their unwillingness to go the extra mile is not the issue, but it is certainly the onset of the problem spreading throughout the organization. Patient zero was Mookie Betts.  
    After Roman Anthony's extension, I was convinced that the Sox were headed in the right direction. They had extended Garrett Crochet and Kristian Campbell; they also made a legitimate financial commitment to Alex Bregman in February, and it felt like they were trending upwards. The league echoed that, too. I would always hear something along the line of: The Red Sox have money to spend and prospect capital to boot, a position other front offices are jealous of.

    And to Craig Breslow's credit, he has made legitimately shrewd moves via trade. Acquiring Sonny Gray, Willson Contreras, and others filled needs. The issue with trades is that now the farm system has lost some key depth, whereas spending money allows them to keep those prospects in-house.

    Knowing what we do now, I can say confidently that the Red Sox would have been better off never signing Bregman at all. There's absurdity laden in that statement, and it's particularly remarkable considering he and Rafael Devers are two of the league's premier hitting talents. But I'll ask you to stick with me for a little while longer — this is a botch-job that rivals the Betts catastrophe.

    In an absolute disaster class from Breslow, he managed to alienate Devers and lose Bregman. We learned on Sunday that the Red Sox would not offer a no-trade clause to Bregman, and based on the final number the Red Sox offered compared to the Cubs (roughly $3 million per year less), it's quite clear that this was the piece that tipped the scales.

    After he witnessed what occurred with Devers just two years into a 10-year contract, why the heck would he not demand a no-trade clause? He's been in the league for nine years and has earned his right to ask for some security, especially knowing how the Red Sox treat their superstars. He has a wife and two kids; stability needs to be a certainty, especially considering this is likely the last major deal he will ever sign.  

    Let's turn our attention back to Breslow. He guaranteed Devers he wouldn't move off third base, or at the very least, gave no indication that Bregman would create a problem in that area. Rightfully so, Devers was upset, and somehow the situation snowballed into Devers being traded. At that exact moment, there can't be a scenario in which Bregman is not on the Red Sox until he retires. As soon as you make that choice, you must commit to it completely.

    It's a trade that signifies a commitment to Bregman at third over Raffy. The problem is, one guy is a homegrown talent making his organizational debut at age 17, signing a 10-year commitment to the organization. The other is on a glorified one-year, $40 million deal. So, if you choose the latter over the former, he'd better be around for a long time, no matter what the cost is. You'd better be willing to get uncomfortable. The $165M was uncomfortable for Breslow and co., but bending over backwards isn't the same as contorting your body in newfound ways.

    Instead, we're out a third basemen entirely, stuck with Jordan Hicks, and the "best" piece in the return, Kyle Harrison, is perpetually stuck in AAA behind a loaded up rotation with plenty of depth. Not to mention, we also traded one of the prospects we received in the package, James Tibbs, for Dustin May

    I try to maintain a glass-half-full view regarding sports. It makes the viewing experience and general consumption markedly better. Yet, even I must acknowledge that there are zero positives regarding this entire situation. The team's improvement had everything to do with Anthony's debut, the front-end of the rotation getting hot, and a career season from Chapman. It had little to do with the "feelings" that Devers may have hurt in two months. They made the playoffs despite the deal, not because of it. They sorely lacked a middle-of-the-order bat in October, and with Bregman gone, they're out another one. 

    Too often, I have seen that the Red Sox feel they have made an aggressive offer, only to be outbid in a measure that is not obscene to have gone to. It feels like a culture problem that goes deeper than just Craig Breslow. 

    What a massive gut punch on the same day as Fenway Fest. There is hope of a turnaround with Bo Bichette being available, but if he is not the infield acquisition that is made, it will be hard to take them seriously as an AL East title contender. Yes, this is likely still a playoff team with or without another infielder. The aforementioned trades have improved the roster, but spending $0 in free agency and the lack of an additional impact bat are glaring weaknesses. 

    Spring training begins in just over a month, and time is incredibly short. Breslow better be ready to get extremely uncomfortable, otherwise this roster he's so delicately built may find itself missing one key piece when October comes roaring back around.

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    I agree with most of what you said. 

    I agree moving off Devers was a big statement. However, these contracts are always hard to figure. A no trade clause shouldn't be the deal breaker. I mean it's a 5 year contract not 10 years and if we are to believe what we thought we saw Bregman is a team leader who will do whatever it takes to win. Not so much for Devers, even though I feel Devers either didn't get sound advice or didn't follow it. Also, I'm not sure but is a no trade clause front page news for a contract or any news at all or are these contracts public knowledge? Meaning Bregman we don't do No Trades but in this case if it is kept between us we can??

    Also, I'm seeing something about deferred money???!!! That was a deal breaker? Again, these contracts are funky, but someone representing the Sox did mention " An aggressive offer??" If we are to believe it was 160/5ys??

    Don't get me wrong, I am a third generation die hard fan and I boycotted this John Henry led team for 2020-2022 for the travesty of losing a generational type player like Mookie Betts( what was the offer??) several years  after you totally screwed up negotiations for John Lester a few years before.

    We have seen the Sox be that team that is in on just about every FA but not getting any outside of Bregman, who had an Op out after year 1 and I'm sure All the Sox brass knew he would Op out.

    They are becoming an interesting organization. I would imagine one of the top 3 or 4 top MLB money makers.



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