In 1960 New York City - the high-powered and glamorous "Golden Age" of advertising - Don Draper, the biggest ad man in the business, struggles to stay a step ahead of the rapidly changing times and the young executives nipping at his heels.

Don continues to conceal his increasingly complicated personal life, even in the face of Roger Sterling's invitation to open up. Meanwhile, Peggy pines for the absent Pete still on his honeymoon while fending off the advances of several of the men of Sterling Cooper.

On election night, the Sterling Cooper staff pulls a rowdy all-nighter while watching the returns. Pete's ambitions cause him to directly challenge Don. Don remembers his past as a soldier in the Korean War.

Don trifft eine alte Bekannte wieder: Anna, die Frau des verstorbenen Don Draper, dessen Identität er im Krieg angenommen hatte. Petes private Probleme machen sich mittlerweile auch im Job bemerkbar - und das bleibt nicht ohne Konsequenzen...