I dont think he hates the Cubs. I think he's one of those types who celebrated all things about his hometown as he moved further and further away from it. White Sox were clearly his preferred team. But the Cubs also wear Chicago on their chest.
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I also think this might be why there initial was confusion about which team he cheered for... its possible (likely) that people close to him were asked if he was a Cubs fan, and they said yes. But they never asked about the Sox until his brothers said he was a Sox fan.
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