Personally it doesn't matter to me. If they want to win the WS they will need to beat the Astros and that's all that matters. Gun to my head I'd say Cleveland just because the Rays usually have the Yankees number.
Judge, I mean come on. Ohtani is pure excitement to watch and the most talented player in the game, but his team finished in last place. I know guys have won the award before in that same situation, and I was oppose to it as well. Judge set an American League homerun record and nearly won the triple crown on a first place team. Not really that hard to decide.