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Pendleton Wise (Vince Vaughn) is a suspicious sort, probably because he earns his living pitching travel scams. His cubicled existence is interrupted by the reemergence of Kelly Grant (Ed Harris), an infamous "room-runner" who, along with lover and business partner Caitlin (Julia Ormond), offers Penny a spot as a top closer in a high stakes mining deal. When Penny and Caitlin start an affair, questions of who's screwing whom lead Penny into deeper waters than he'd anticipated. Wikipedia