ports agent Rob Sherman hires a career burglar, Dewey Jordan, to "burglarize" his house as part of an insurance scam, which turns out to be his cover up for a murder. As soon as Dewey enters the house, Sherman shoots him dead with one gun. When his wife comes downstairs to investigate the noise, Sherman shoots her with another gun, which he plants in Dewey's hand to frame the 'burglar' for the second murder. Monk is brought in to investigate, and immediately suspects Sherman, but Sherman has covered his tracks very well. Meanwhile, Natalie's daughter Julie is having relationship problems with her boyfriend Tim Sussman when she starts seeing a quarterback named Clay Bridges. Monk finds that Julie's love life is related to the murders.

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