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Apparently suffering from a mid-life crisis that causes moments of bizarre whimsy, billionaire computer executive Sidney Teal (J.C. McKenzie) pulls a gun and attempts to rob a couple outside a restaurant--and is killed in the process. Though beset with financial problems, and facing the possible loss of his trusted nurse Sharona (Bitty Schram), Monk (Tony Shalhoub)agrees to investigate Teal's death, and the reasons behind it. Perhaps the answer can be gleaned from the two people whom the dead man mugged...or perhaps the solution is in the hands of Officer Moretta (Jonathan Rannells) the cop at the crime scene who inexplicably ran away before back-up arrived--and hasn't been seen since. (Note: the scene in which Monk discusses clues pertaining to the earlier death of his wife with writer Kelly Street [Mary Black] was actually filmed for, but removed from, Monk's two-hour pilot episode).