 Natalie Teeger ( Traylor Howard ) is fighting traffic to get Adrian Monk ( Tony Shalhoub ) to his appointment with his psychiatrist , Dr. Kroger ( Stanley Kamel ) . Monk says he hates to miss his sessions . Natalie confides to her daughter Julie ( Emmy Clarke ) that Monk 's wife , Trudy , died in December ten years ago . They come to a dead stop when retired parole officer , Michael Kenworthy ( Randle Mell ) , in a Santa Claus outfit , showers toys on the street from a roof . Furious , Monk heads up , and Natalie and Julie hear shots . On the roof , they see Monk holding a gun , and Kenworthy shot . Captain Stottlemeyer ( Ted Levine ) and Lieutenant Disher ( Jason Gray @-@ Stanford ) arrest Monk . Monk says that Kenworthy is the owner of the gun , and he shot him in self @-@ defense , but Kenworthy denies this , saying Monk attacked him . 
