MM will sign with whoever makes him the richest man possible. If that is the Yankees, that is who he will sign with. If that is the Reds, that is who he will sign with. Its that simple.
Assuming they trade Gray, they still need at least another SP.
Tanaka, Severino, Paxton, Sabatha.......
I doubt htye plan to run Montgomery, Adams or AJ Cole out there every 5th day.
I don't see the Grandal fit at all. Seems like a poor use of resources.
Now if the Sox trade Narvaez and Collins this offseason, maybe it makes more sense.
Not only a loss of pick, but catcher isn't really the position the sox should be spending big dollars. They already have 2 major league catchers on the roster, and another two interesting prospects that are pretty close. Much bigger holes to fill.
If you take out Avi's unsustainably high BABIP-fueled 2017, he has been a pretty terrible player. He's a low OBP corner outfield that sucks defensively. He isn't woth the $8-10M he will would get in arb. He's probably looking at 1 year deal around $5M with someone else if the Sox non-tender him, and he may very well outperform that contact. But his time with the Sox is likely over. Its time to move on.