Dr. Jay Bennett is a murderer who appears in the Season 5 episode "Mr. Monk, Private Eye". He was portrayed by Frederick Weller.
A Sinking Relationship[]
On a night in 2006, Bennett took his luxury boat, The Lucky Lady, out into the Southeast Barrier with his mistress, married schoolteacher Anna Pollard. When he asked her why she had been so quiet at their dinner at a bar known as Joel's, Anna reminded him of a conversation she had had with him before in which he stated she needed to choose between him and her husband Eric. She stated she ultimately chose her husband and was leaving Jay. She had only come onto the boat and not said much at dinner because it was his birthday and she didn't want to ruin the day for him. Jay tried to make Anna stay with him and even offered to take her to a paradise for the week, but Anna stood her ground and said it was over. As Bennett was angrily climbing to the boat's controls with the champagne he had prepared for the two of them, he spat that he assumed she told her husband everything to try and save their marriage. To his surprise, however, Anna stated she hadn't told her husband anything, citing that her shame about the affair as the reason she hadn't.
Seeing the opportunity for revenge, Bennett climbed back down the ladder and swung the champagne bottle at Anna's head. He then proceeded to lock her in a metal crate with holes in it, then threw it into the bay, drowning Anna if the blunt force trauma hadn't killed her first. In the process, the anchor of the boat got some of the Southeast Barrier's bull kelp stuck to it.
Working Out Some Dings[]
He then sailed his boat back to his slip at the marina, going the wrong way out to avoid being caught on the marina's security camera. In the process, he hit the parked car of real estate agent Linda Fusco. The hit was noticed by a late night sea captain by the name of Bill Gibbard. Bennett left a note on the car (reading "Go To Hell!" on it, likely due to his panic and frustration) to keep Gibbard from reporting the accident, which could place him at the scene of where Anna went missing if it was found out that she had been there. What Jay found out later was that Gibbard had noticed him and Anna leaving the marina in the boat, and now only Bennett had returned. Bill deduced that Jay must have killed Anna, but kept quiet after Jay offered him a bribe.
Unfortunately for Bennett, his refusal to pay the damage for Linda's car (or at least the needlessly aggressive note left on it) inspired her to hire a private investigator to find whoever had hit her car and make him pay for the damages. After a couple of days, she found one in Adrian Monk, who had started the business at the insistence of his assistant Natalie Teeger. Monk's investigation led him to try and ask Bill if he saw the accident or knew anything about it. Bill lied and claimed he didn't see anything.
Later that night, Jay returned to the marina to pay Bill off for his silence as the captain was getting ready to go out for fishing. Bill then asked for double, as he figured if a private investigator was asking around, cops may follow, and thus the raised price. Bennett told Bill he would double the money, but when Bill turned around to collect more equipment, Bennett knocked him out from behind with a large piece of metal and then threw him into the water, drowning him. Said act was witnessed by Bill's dog Eggy.
Smooth Sailing[]
Bennett and Monk's paths soon crossed the next morning, when he found him and Natalie waiting by his car. Bennett began to panic and was on the verge of surrendering until Natalie explained that Adrian was actually investigating the fender bender and not Anna's disappearance. Thus, Jay began to relax and blew off the duo's request to pay the damages to Linda's car. He drove off, later returning to The Lucky Lady to sail out into deeper waters and dispose of the remaining evidence of Anna in his life.
What Jay didn't know was that Adrian had earlier boarded the boat himself, and had found one of the flip flops Anna had last been seen wearing. He eventually did realize it, put the boat in cruise control, and held Monk up with a spear gun. He threw the flip flop into the bay and prepared to shoot Monk, but a wave knocked Jay off his feet, giving Adrian the chance to scale the side of the boat. Around the same time, Natalie has noticed Eggy barking and found Bill's body. She, Captain Leland Stottlemeyer, Lt. Randy Disher, and Linda sailed out to the water on Linda's boat and managed to pull Adrian out of the water after he had jumped off The Lucky Lady and stayed swimming in the water. As the Coast Guard sent out a boat to intercept Jay, Adrian helped the police locate where Anna was dumped after noticing the bull kelp on the anchor, having seen the same kelp on Bill Gibbard's propellers. Jay was arrested for the murders of Anna and Bill.
Coincidentally, Linda would be found guilty of murder a year or so later, with the murder solved by Adrian Monk as well.