They both have their advantages and disadvantages. I honestly think it's who lands "the big one" first (I'm leaning towards Judah on that one). The reason i say that, both have terrific power. Maybe not one punch KO power but one punch leave you dizzy and defenseless power. Also, neither guy posseses what i would call a granite chin.
With that being said, my pick is....Judah in an upset (but i wouldn't put money on it).
I will be rooting for Cotto though as he's one of my favorite fighters.