In a vacuum, I can't blame the Sox for not wanting to pay that amount for Bregman. In a vaccum I see merit in setting a value on guys and not getting desperate to overpay for them.
But in the aggregate, looking back year over year and missing out on pretty much every higher mid tier to high tier free agent that fits there needs is unforgivable.
Maybe Bregman isn't the guy, but at some point you have to move out of your comfort zone a little. Having Bregman for one year was fine, but giving up a high draft pick for a guy is not good business and now they're pretty much in a position of Bo or bust. I get they can still trade for a guy, but you can't build your entire team trading for guys, at some point you're going to run out of ammunition.