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Can the man in the suit really become the face of the city?
He has plenty of things going for him. He brings success to the city that hasn't had much recently. He's not just looking for a headline or newspaper quote as some management position on the South Side.
Is hockey popular enough to produce the face of the city?
One could argue that it's Brian Urlacher, who's manned the defense for the Chicago Bears for the last 12 seasons. But have the Bears had enough success to do so?
Epstein possibly has a better chance than Derrick Rose, because he's at least capable of taking his own SATs. It's also tough for Rose to overcome the shadow left by Michael Jordan over Chicago basketball.
Chicago is a Cubs town. But Epstein, no matter how many championships he brings, cannot be that face.
It needs to be a player. Fans come out to see the players perform instead of seeing Epstein sip on a bottle of water in his box seat.
Perhaps it becomes homegrown talent such as Starlin Castro or Brett Jackson. Maybe Anthony Rizzo emerges as that player.
Whoever it is, a player in pinstripes must take the responsibility and pride to become the face of the city, much in the way Sammy Sosa was back in his prime.