This year more than any other in recent memory, free agents both good and bad struggled to find a home. Even now, the market is still not exhausted. Reclamation projects such as Tim Lincecum, Justin Masterson, and Kyle Lohse linger, while the Orioles just released former Red Sox farmhand Miguel Gonzalez.
The Red Sox, of course, have never been ones to shy away from a reclamation project. Some have worked, probably more have not. But when given the choice between a starter who has a chance to be an impact player at a bargain price, and a weak #5 who has no such chance, the Red Sox have generally elected for a coin flip.
This year, however, seems likely to be different, and it's not just because there's a new man in charge. It's true that there are few who would claim to be comfortable with Boston's starting options. But the important factor here is why any given fan would be uncomfortable. It's not because the Red Sox are full of mediocre back-end types. It's because seemingly their entire rotation after David Price is made up of this sort of coin flip player. Be it due to injury risk, inexperience, or the questionable ability to turn Great Stuff® into great results, the Red Sox' pitchers are the sorts likely to be very good, or very bad, rather than trending in-between.
Now, typically, the Red Sox would still be happy to add someone like Miguel Gonzalez into that mix. The best way to protect yourself against those coin flip players is to add more of them. If you go looking for four heads, a dozen flips is going to give you a much better shot at that than eight will.
Unfortunately for Boston, the pitchers have rather a lot of say in where they end up as well, and while some of them might be getting desperate, it's one thing to be desperate enough to accept a minor league contract, and another thing to be desperate enough to sign a minor league contract to compete with Henry Owens, Brian Johnson, Roenis Elias, and eventually Steven Wright for the privilege of being first in line when/if the Red Sox find themselves in need of another starting pitcher.
And beyond that, there's the question of where that player eventually goes to play. If you're a pitcher of uncertain quality with a sinking reputation, Fenway Park is not the best place to build your stock back up. It's not even in the top-20. Yes, if those pitchers are really sure of themselves, maybe it makes sense to go for the big gamble--after all, if you can cut it in Fenway Park, you can cut it just about anywhere. But more practically, a pitcher like Miguel Gonzalez, still shy of his first big payday, should probably be looking for a National League team with a nice big outfield.
So while we might be hearing about these players showcasing themselves for various teams in the coming days, and we may well even hear that the Red Sox are one of those teams involved, chances are that nothing will come of it. They're just not a good fit.