Red Sox's Latest Blunder Revealed As Alex Bregman Fallout Continues

How can you be unwilling to meet this particular demand?

Dec 9, 2024; Dallas, TX, USA; Boston Red Sox chief baseball officer Craig Breslow speaks with the media at the Hilton Anatole during the 2024 MLB Winter Meetings. Mandatory Credit: Jerome Miron-Imagn Images | Jerome Miron-Imagn Images

The Boston Red Sox's series of unforced errors continued on Saturday night with the news of Alex Bregman's departure.

Bregman reportedly agreed to a five-year, $175 million deal with the Chicago Cubs, and the Red Sox were quickly confirmed to be outbid. But on top of the money, there was another manner in which they missed the mark here completely.

According to Peter Abraham of The Boston Globe, Boston balked at the idea of giving Bregman a no-trade clause, which he is set to receive when he signs with Chicago.

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Red Sox wouldn't give Bregman no-trade clause... why?

"Per several sources: Red Sox were not particularly close at the end with Bregman. The no-trade clause also was an obstacle," Abraham wrote on Bluesky.

The money obviously mattered quite a bit. We heard from insider Jon Heyman on Sunday that the believed Boston came in at around five years and $160 million, which isn't necessarily a bid one can fault them for.

But they undeniably let this thing drag out too long, and one would have to assume there was deferred money included in that offer to bring down the present-day value. Yet this failure on the no-trade clause sticks out like a sore thumb.

There are times in a player's career when they don't particularly deserve a no-trade clause yet. If you're giving a second-year star a long-term extension, maybe you leave the no-trade clause out. But Bregman, who will reach 10 years of service time in the final month of the regular season, isn't one of those players.

That the Red Sox saw this as any sort of an obstacle could have easily been a tiebreaker, even if Boston had been given the opportunity to match every dollar the Cubs were putting forth.

And recent history matters here too. Bregman was probably looking at the Rafael Devers situation and saying to himself, "Well, these guys clearly will trade anyone, so why should I be confident they won't do it to me?"

It's just another example of the Red Sox talking a big game about wanting championships, but being too cautious in their approach to make the moves championship teams regularly make.

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