Jessica flies to Italy to visit Salvatore Gambini, as he celebrates his 75th birthday. Salvatore feels great pride in his winery, only wishing he could pass on that pride to his heirs. However, wine and song become the least important part of the visit when a suspicious "accident" injures grandson Tony, and then granddaughter Michele's latest boyfriend winds up dead in the wine cellar. Jessica suspects the incidents have something to do with someone pressuring Salvatore to sell, and she's willing to hunt through the dregs of society to find out who's threatening her friend.
This episode includes examples of the following tropes:
- Death by Falling Over: Invoked and subverted. The hitman sawed partway through a step to the wine cellar to kill his target in an "accident", but Salvatore's grandson Tony falls victim instead, and only gets banged up.
- Driven to Suicide: Salvatore Gambini. He's terminally ill and, knowing his granddaughter's boyfriend was a hitman, wants the guy to end his pain so he can relinquish his company to his family. However, when one of his grandsons almost gets killed in a trap meant for him, he goes Papa Wolf and poisons the hitman's wine. He later tries a more direct form of this when he poisons himself with the same wine after confessing to the murder. Fortunately, he is saved from death offscreen thanks to quick medical attention.
- Make It Look Like an Accident: On a hunch, Jessica looks at the step that gave way. She sees that it had been partially sawed through, implying someone sabotaged it to kill someone in the house.
- Saying Too Much: When he's talking to Jessica, Salvatore refers to Mr. Schuyler as a bum from New York. However, Schuyler had claimed to have grown up on a farm in Illinois. Therefore, Salvatore had to have discovered at some point who his granddaughter's new boyfriend really was — namely, a mob hitman.
- Sympathetic Murderer: the victim was a professional hitman. Jessica's friend had actually invited the hitman to his house as part of an admittedly foolish Thanatos Gambit, but then the hitman's sloppy attempt at murder badly injures the man's grandson instead, prompting the old man to off the hitman himself, confess everything to Jessica, and then attempt suicide. It's especially notable in that Jessica herself says that she would refuse to testify about his confession, as she sees no need for him to go to jail (he's terminally ill).
- Tampering with Food and Drink: The victim, a mob hitman, dies when Salvatore Gambini poisons his wine. Salvatore scoffs that the guy didn't taste anything and it was a waste of the good wine he used.
- Thanatos Gambit: Salvatore wants to pass on his vineyard to his family, but none of them care much about it at all. After learning that a crime syndicate who wants his land has put out a hit on him, he deliberately invites their hitman to his house, hoping that if he is murdered, it will inspire his kids to work together and protect the winery. The plan doesn't go exactly right, and he ends up not even dying, but the mere attempt ends up accomplishing his goal anyway.