Whitley started his career as a Directors Guild of America trainee on The Last Word and The Blues Brothers, before moving to television as a second assistant director on A Man Called Hawk (starring Avery Brooks), Freddy's Nightmares, and Family Matters. Whitley joined the Star Trek: Deep Space Nine production team in 1994, with his first episode as a first assistant director being "The Alternate" . Whitley left Star Trek: Deep Space Nine in 1995, working on just one episode of the fourth season, "Hippocratic Oath" .
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