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Maybe that's why he's always so hard on Baker, because he has a fandom for the Browns yet. According to the article below, at least from what I see, is that he was once a fan of a couple of the Browns QBs in the past, getting a jersey for Sipe when he was a kid I guess. So it sounds like at one point in his life, he was a Browns fan. So maybe he's just fed up that the Browns aren't perfect or don't have a QB who's winning them a bunch of games.
www.brownsnation.com
So in theory, I think Colin Cowherd is a fan of the Browns or was and just wants to see this team succeed as a fan would.

Colin Cowherd Reveals Something That May Surprise You
While talking about the Cleveland Browns and Baker Mayfield, Colin Cowherd dropped an interesting and surprising tidbit.

So in theory, I think Colin Cowherd is a fan of the Browns or was and just wants to see this team succeed as a fan would.