39. Ted Phillips
The McCaskeys own the team, but this native East Coaster supervises daily operations and is said to have the ear of principal owner Virginia McCaskey. A 28-year organization vet, he gets credit for the Soldier Field renovation and also was responsible for hiring—and firing—GM Jerry Angelo. His stock could rise if he hires the right talent to help the Bears keep pace in the NFC Central.
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Photograph: Brian Cassella/Chicago Tribune