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While there are some fences he could have crashed through, in the background are always buildings.

Chink (Sonny Landham) was instructed by warden Drumgool to antagonize Leoni from the moment he got to Gateway penitentiary. He was probably promised early release or other special privileges in return for his services. Remember that Drumgool promised Tom Sizemore's character early release in return for setting Leoni up during the escape attempt in the tunnels, and then Drumgool betrayed him saying "this prison doesn't make deals with escapees".