The biggest obstacle the Yankees might face is the potential obtainable of the Marlins' GM. If he insists on Judge and won't move, the Yankees undoubtedly walk.
And we've all seen teams that don't budge on their demands. Some do negotiate, which is why Benintendi is still in Boston after the Sale trade. But some don't, which is why Cole Hamels isn't in Boston and his former stubborn GM is, coaching first base....