Don Draper is shaken when his past life comes back to haunt him. After his picture appears in a local newspaper, Adam Whitman, a man who claims to be his younger brother, approaches him. Don, or Dick as his brother knows him, initially denies everything but in the end admits to having taken on a new name. He refuses however to have anything to do with him and tries to buy his silence. When one of the ad men gets a short story published, Pete Campbell is frustrated that his own stories have yet to see the light of day. When his wife approaches an old beau to see if he will publish the stories, he has an interesting proposition for her.

The Agency is looking to land an advertising contract to promote tourism to Israel. Don and his team try to come up with a theme but know so little about the country that they're stumped. So Don calls Rachel Menken to see if she has any ideas. Roger Sterling is getting tired of sneaking around with Joan Holloway and suggests she should get her own apartment but she knows better. Peggy comes up with an advertising concept during a testing session for a new line of lipsticks and she's subsequently asked to write copy.

Don is courted by Jim Hobart, head of a larger ad firm who offers him more money and more creative resources to join them. Betty Draper rekindles her interest in modeling after Hobart suggests she should try it. She doesn't realize it's all part of the strategy to get Don on board. Peggy Olsen is fretting over her weight gain but doesn't appreciate Joan's advice about getting ahead in the office. The ad team tries to counter the advertising coming out of the Kennedy campaign. Pete Campbell comes up with an idea to keep Kennedy's image off TV in key States.

Election night arrives and the staff of Sterling Cooper has a party while watching the returns. The election is close and it's obviously going to be a long night. Now a senior partner in the firm, Don Draper must hire a new head of account services, a post that Pete Campbell yearns for. Aware of Draper's secret past, he tries to strong-arm him into giving him the job. With his secret out, Don panics and he asks Rachel Menken to run away with him. Regaining his composure, Don calls Pete's bluff leading to a confrontation with Bert Cooper.

On Valentine's Day, the staff of the Sterling Cooper Advertising Agency is hustling and checking out the newest office equipment. Don and Duck clash over an account, and Betty hears from an old friend.

A plane crash causes the firm to go after the account for the airline involved and drop the smaller airline they have an account with. Peggy pays a visit to her mother and sister, who are now guardians of a child.

Trouble rises on the set of a commercial while Don plays hooky from the office.

Freddy and Ken take a client out to lunch who stirs Roger Sterling's heart.

Joan finds Don the perfect secretary, and Don finds himself in the middle of issues between TV comedian Jimmy and his wife, Bobbie.

Don and Duck try to bury the hatchet, and Peggy attempts to join in on the execs' after-hours meetings. Also, Duck receives a family visit at the office.

To show that he has "arrived," Don buys a new car. Pete, Harry and Ken come up with a plan to attract new business, and Don's secretary makes a serious error, which could mean trouble for Joan. Cooper gets a new piece of office art that attracts the interest of the Sterling Cooper staff.

Betty becomes suspicious that Don is having an affair after her conversation with Jimmy Barrett, Joan helps out in the television department, and Peggy helps the church with a dance flyer.

Don checks in to a hotel after his separation from Betty. Back at the office, he is forced to get rid of Freddy against his will because of his drinking problem.

Don drops off the Sterling Cooper radar and visits the wife of the man whose identity he stole. Back at the office, Bert and Roger consider the merger offer, Peggy makes a play for a real office, and Peter loses his father-in-law's account.