We’ll see I guess but Boras has a pretty good track record that I wouldn’t bet against. I think a scenario that’s just as plausible is that Monty/Snell already have homes and Boras is just trying to extract the most he can before signing. The value in having both Monty/Snell as clients is that he knows what offers are out there for both. There is no chance for the interested teams to pivot to someone else as all the other quality free agent SPs are signed and the trade market seems frozen.
Do you mean, like, they have a handshake agreement with some team and Boras is just waiting to see how much more he can get from them? This just doesn't make sense to me. Why would any team just wait around thinking, but not knowing, they could be putting $20M+ over multiple years on their books, but it isn't a done deal yet? I am sure there are offers from multiple teams, but I highly doubt that either of them have an offer that Boras has said, "Yeah, we will sign that, but give me time". Maybe I am reading your post wrong, but I just don't think any team would let Boras hold them hostage like that, and if they are, then whoever is in charge should probably be fired.
I think more likely is that most teams are actually really smart and see what a lot of people here see, that these are two very good, but flawed pitchers. You are signing peak Verlander or Scherzer here, where if there is a small decline you are still looking at a borderline Hall of Famer instead of a sure thing. If Montgomery's HR rate ticks back up to what it was pre-Cardinals, and his K-rate drops from his already rather pedestrian 7.9 per 9, all of a sudden you have a good (and maybe even mediocre) pitcher instead of a very good one. Likewise, if Snell gets out of San Diego and his HR rate climbs back up to 1.1 or 1.2 like it was in his Rays days, those walks are going to start hurting that much more. And if his control gets worse and that 11.5+ K rate starts turning into a 6+ BB rate (he was already at 5 this year)? That' scary to think about, and it isn't my money.
I still really hope the Sox find a way to sign Montgomery, I think he instantly makes them a Wild Card contender in 2024, and my hope as a fan is to simply see meaningful baseball in September, as championships every season simply aren't a reasonable expectation, though one can hope. I think Montgomery makes important games in September and October more likely (I am not as convinced on Snell, his profile scares the bejesus out of me in Fenway and in front of the Red Sox defense). I also won't think it is the end of the world if they don't sign him, because I think they can still be competitive into September with what they already have, and would likely add a pitcher from the next tier if they do fail to sign Montgomery.