One night he meets up with a woman (despite being married) and makes out with her. After an accident, he finds out a teddy bear was hiding a camera. Michelle tries to get it, but Jack already spotted it. Suspecting blackmail, he demands what is going on, and tries to wrestle the camera from her. A push sends her into a counter, which kills her. Jack then flees the scene.
During the struggle, his watch was broken, and he needs a new one. It also turns out that he went with Michelle to a restaurant earlier that painted the customers on the wall. Knowing he would be in trouble if his wife saw the wall with the painting, he goes to the restaurant and breaks out the wall section with him and Michelle. Coincidentally, a pawn shop is on the other side of the wall, which he goes into and steals a watch after taking some cash. However, the owner appears with a gun. Jack slowly approaches him and wrestles the gun from him, shooting the owner once and then fleeing.
Later, Adrian Monk pieces the broken wall section together, revealing Jack Leverett. The police then set out for him.
While at his auto dealership, a vigilante-style man (David Rusken), who believes he is Adrian Monk, holds Jack at gunpoint, mistakenly believing Jack is Trudy Monk's killer. In the end, the real Adrian Monk convinces David that this isn't what Trudy would want, with David releasing the gun.
Handcuffed to a car earlier by David, it is most likely that the police then came in and arrested Jack.