The love story begins on Miami Vice! Castillo pulls Crockett off an arms investigation so he can guard Caitlin until she testifies at Lowe's trial because he "blends in with the music crowd". Crockett is annoyed, thinking this is all a publicity stunt, but agrees to the assignment.

From Miami Vice Season 4 Episode 8 “Like a Hurricane”: Crockett is assigned to protect a witness in a payola case, and ends up falling in love.

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