Duck brings word that Martinson's Coffee might be willing to jump ship from Grey's, so they bring in those Smith kids they apparently hired a few episodes ago, who give Don the insight that the younger generation doesn't want to be told what to do or how to act. The Smiths pitch a campaign in this vein, which is a success, and Duck and Don congratulate each other. Don's the only one who gets kudos from Bertram and Roger, though, and they in fact invite Don to get involved in a philanthropic cause, the idea being that Don will be a far more visible representative of SC than he has been in the past. In that vein, they get Don to buy a Coupe de Ville, which leads to a flashback to a time when he was a used-car salesman and a woman came to see him who knew he wasn't the real Don Draper.
Bertram has a new, expensive painting in his office that everyone's curious about, and Jane leads Ken, Sal, and Harry on an expedition to check it out, but Joan gets wind of it, as she always does, and cans Jane in a flash. Jane, however, through a damsel-in-distress routine that might or might not be genuine, gets Roger to intercede on her behalf, which of course means that Joan ends up thinking Jane is her replacement, and sure isn't happy about it. Meanwhile, Ken's unforeseen appreciation for the art endears him to Sal, as does his request that Sal look over a new story of his. Sal invites Ken over for dinner with him and his wife, and the gay desire coming off Sal makes Ken vaguely uncomfortable and his wife upset and jealous.
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