A successful television producer in Los Angeles, Dwight doted on his only child, and was very proud of her for winning scholarships to an exclusive private school, and to UC Berkeley.
When Trudy and Adrian Monk fell in love, she brought him home to meet her parents. Since Adrian was already a successful young detective with the SFPD, Dwight offered his future son-in-law a job as a technical adviser on a new cop show he was producing. Adrian hesitated, and Trudy declined for him, saying Adrian was born to be a detective, and they both loved living in San Francisco. Monk later felt guilty over this decision, feeling that, if had accepted, Trudy would not have died.
Like his wife, Marcia, Dwight never entirely recovered from the loss of his daughter. He continued working, though, and kept in contact with Adrian. Seven years after Trudy's death, he asked for Adrian's help in exposing the current champion of his current game show, "Treasure Chest," as a cheat. Adrian went one better, also exposing the show's host, Roddy Lankman, as a murderer.