Here’s what I think is happening.
Boras is putting the screws to the Sox. (Other agents have followed suit). He knows that we're in a protracted PR crisis after Mookie, and that Winter Weekend is approaching, and Breslow and the Sox FO want to avoid another spectacle in his first year. You could argue that this kind of pressure led to them getting Devers’ extension done last year (two weeks before Winter Weekend).
One of the reasons Boras loves taking his time with free agents is that he knows that owners and front offices risk losing their fan bases' attention over the winter, or worse, rousing their derision. He uses the media well, knows that news cycles are as short as everyone's attention spans. Good reporters at reputable outlets (Speier at the Globe) uses what Boras will give him cautiously, knowing full well that it's clearly self-serving info but also not wanting to burn a source. Other reporters at outlets whose business models prioritize engagement rather than informing the public, they're happy to use what Boras gives them. And why not? The Sox aren't talking.
Snell and Montgomery are good pitchers, but there are perfectly good reasons not to want to overpay them. The former, an inferior one to David Price when we signed him, wants similar money at $200+ million. The latter, inferior to Chris Sale, wants a contract that far exceeds Sale’s extension. Snell, from Seattle, reportedly wants to stay on the West Coast. And
the Rangers are reportedly Montgomery’s “first choice.”
But now Boras has for months laundered the idea that if the Sox don't wildly outbid the field —
or at least wildly bid up the cost — for his very good starting pitchers, they will have failed their fans and become a "small-market team."
It's smart strategy on Boras's part. He's doing his job. I'm not arguing that he's
bad or anything like that. (I think baseball players should be paid a greater share of total MLB revenue than they are, but I also want the Red Sox to be smart about roster-building within the rules of the game.)
However, we should recognize that Boras is under no obligation to provide information that is
true. If he tells Cotillo that the Red Sox are acting like a small-market team, it is no more true just because the Red Sox don't bother to deny it on the record. And nobody — not the Red Sox, not the reporters — are at liberty to tell Boras to buzz off. They all need him to return their phone calls, and vice versa even more so.
Regardless, neither of Boras's guys sign before Imanaga. If he chooses the West Coast too, the pressure on the Sox increases. We whiff on all three and it's confirmation bias city. Everyone howls louder, harder, and we’re in some kind of ownership crisis. Or deeper in one.
Breslow, sensibly, would rather not cave to this kind of pressure in his first year. And, I think rightly, doesn’t want his legacy immediately tethered to the outcome of a risky, prohibitive contract for a very good-not-great starter (one of them seemingly not a great clubhouse guy). He probably likes Burnes and Fried more (I do), and may want to bid on Soto or Vlad Guerrero Jr. next winter and the following. I think he's legitimately in on Imanaga and cautiously in on Montgomery (Feinsand has reported we're in on "two of" BS, JM, and SI), and probably has a deal lined up for an outfielder or two, depending on which hitter or hitters we sign in the next week or so.
I also think it's all going to be fine. The AL East is a dogfight as always, but we're in really good shape going forward. The core is really interesting, and it includes more young pitchers than people realize. The key is not dropping nine-figure deals on guys to complement them when they're obviously bad fits.