Martin Sheen as Joe Maddon
Slap some black glasses on Sheen and mess his hair up a little bit and I think you’ve found your Cubs skipper. I think Sheen may have to smoke some dope to get that calming demeanor that Maddon has but that’s something I’m sure he’d be willing to do to get into the role.
C’mon, he’s Charlie Sheen’s father.
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Big shout-out to Period E for the input on the actors.