It's close but I'd probably go with Benintendi. I don't think you can assume Freeman will get traded and Benintendi in Bostons lineup will get a ton of counting stats. AL east is full of hitters parks too
It really doesn't matter. A Manger has little to zero impact on the total amount of wins at the end of the year. Yeah, Gibby is dumb but so are a bunch of managers. Players seem to like playing for him and that's important in attracting talent to come here.