Fresh off a high-profile assassination, Dan is stunned to learn that JFK has discovered his CIA side gig. Dan attempts to lie low, only to be kidnapped and extorted by Jack. In the present Brent tries to come to terms with the revisionist history he is being spoon fed. With no other choice, Dan aids the Kennedy campaign, resulting in Jack’s election. After being summoned to New York, Dan learns that Jack has no plans to let the team out from under his thumb, forcing him to capitalize on Jack’s one weakness Marilyn Monroe. Beginning a relationship with Marilyn, Dan secures her as a source of intel to use against Jack.