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Roger Sterling, Jr. is a founding partner at Sterling Cooper Advertising Agency Advertising Agency in Manhattan, NY. Prior to that, he worked for the Sterling Cooper advertising agency. ("Smoke Gets in Your Eyes") Roger Sterling, Sr. was one of the founders of Sterling Cooper in 1923.
Roger's past has been pieced together through his many recollections during the show. As the son of Sterling Cooper co-founder Roger Sterling Sr., Roger grew up in wealth. Always nautically minded, he claims to have sailed a tramp steamer to Hilton Head as a young man, though it was later revealed to have been a yacht.
As he often mentions, Sterling is a World War II Naval veteran. Prior to his deployment to the South Pacific, he was in an intense relationship with Anabelle Mathis, heiress to the Caldecott Farms dog food company. She ended their affair shortly before he shipped out, leaving Roger devastated.
In "Red in the Face", Roger's war recollections suggest he was the skipper of a ship running fuel between islands. Later in Season 4, however, he begins to tell Joan a story about being onboard a destroyer. For his time in the service, Roger was given a medal, and has since harbored a hatred for the Japanese.
Following the war, Roger began to work at his father's company, where he takes a dislike to fellow veteran Freddy Rumsen, believing him to have been a "coward" in the Signal Corps. The animosity disappeared when Roger learned Rumsen was only put there after having killed a number of Germans in combat.
Some time in the 1950s, Roger enters Heller's, a specialty shop dealing in fur coats to buy Joan a fur coat, where Don Draper is employed as a salesman. Roger comments on an advertisement for Heller's and Don states that it is one of his own. Roger hands Don a card showing that Roger works for an advertising firm. When Roger opens the box for Joan in a hotel room, he realizes that Don has included a portfolio; he considers Don to be "out of line" for including it.
A few days later Don runs into Roger in the lobby of Sterling Cooper, and tries to explain it away as coincidence. He asks Roger if he saw his work; Roger tells him that it was thrown away with the box. Don offers Roger a drink, and though it is 10am, Roger accepts. Over drinks, Don tries to sell Roger on the idea of hiring him. A few days later, Roger sees Don in the lobby again, waiting for the elevator. Roger is beside himself, angry that Don could not take a hint that he was not interested. Don stops Roger; while they board the elevator, he reminds Roger that he had hired Don the previous day. Don smiles as Roger appears confused about his lapse in memory. ("Waldorf Stories")
On the Friday before Labor Day weekend in 1960, Sterling Cooper loses the Dr. Scholl's account. Roger attempts to cheer Don up by arranging for a pair of twins to spend the night with them. This results in Roger having a heart attack. ("Long Weekend") The following October, Roger returns to the office, but has a second heart attack during a meeting with Lee Garner Sr., the head of Lucky Strike. As a result, Don is offered a partnership in Sterling Cooper. ("Indian Summer")
In 1962, Roger begins an affair with his secretary, Jane Siegel. He eventually leaves Mona, and proposes marriage to Jane. They married sometime in early 1963. Their happiness is short-lived, and their marriage causes friction between Roger and his daughter, Margaret, who asks that Jane not attend her wedding.
A New Company
When rumors of the purchase of Putnam, Powell and Lowe, parent company of Sterling Cooper get out in December, 1963, Don pushes Bertram Cooper and Roger Sterling, the original senior partners, to attempt a re-purchase of the company. After presenting an offer, they are rebuffed, until they hit upon an idea. Lane Pryce, the representative from PPL with authority over everyone at Sterling Cooper, agrees to fire the senior partners, thereby severing their contracts (including the no-compete clauses in their contracts) and join them in forming a new agency.
They secretly round up a list of clients loyal to them and steal important documentation that will assist the transition. They also quietly select the first employees: Pete Campbell, Peggy Olson, Joan Holloway, and Harry Crane. ("Shut the Door. Have a Seat")
Sterling Cooper Draper Pryce (SCDP) receives word that Honda is looking for a new advertising agency. Roger blames the Japanese for the deaths of his friends during World War II and states that he does not want their business. In order to enable SCDP to proceed without Roger, Pete plans a meeting for Roger to attend; it would take place at the same time that the Japanese were in the office so that Roger would have no knowledge of their actions. In the middle of the meeting with the Honda executives, Roger bursts into the office and starts a rant, stating that they "don't want any of your Jap crap." After he leaves the room, the other members of SCDP apologize for Roger's rude behavior; in the folowing days, they realize that they have likely blown their chance when Honda does not send them a gift.
After the initial meeting with Honda, Pete accuses Roger of sabotaging the meeting because, if SCDP started doing business with Honda, they would became "less dependent on Lucky Strike and therefore less dependent on [Roger]." Roger rushes Pete, but Don steps in between the two men. After Pete leaves the room, Don tells Roger that Pete was right about this characterization. ("The Chrysanthemum and the Sword")
Roger and Don plan on seeing the Muhammad Ali vs. Sonny Liston fight on May 25, though neither are happy about having to go with the Alcoholics Anonymous members, Freddy Rumsen and their client from Ponds. Don eventually cancels his plans to see the fight, much to Roger's dismay. ("The Suitcase")
While Joan's husband is at basic training, Roger takes Joan out for dinner. While commenting on the condition of the neighborhood they are walking through, a man mugs them at gunpoint. Roger acts quickly, lowering his head and handing all their possessions over to the mugger. After the mugger runs off, Roger and Joan stop to catch their breath; they began to kiss and make love to one another while pressed against a fence. ("The Beautiful Girls")
Roger and Lee Garner, Jr., an executive at Lucky Strike, have dinner at a restaurant. When Lee requests to pay for the meal, Roger senses a problem; Lee apologizes, and tells Roger "It's over, " that Lucky Strike is cutting ties with SCDP. He states that the board would like to consolidate the company to one firm, BBDO. Roger, visibly shocked, tells him that this is not the way that families treat one another; he points out all the times he had to lie to cover for Lee. Roger then attempts to haggle with Lee for a 30 day period in which to try and convince Lucky Strike to change their minds. Roger hands Lee's money back to him and pays for dinner himself. Later that night, he makes calls to old contacts, trying to track down new work for the firm. ("Hands and Knees")
Ken Cosgrove runs into an account executive from BBDO, who slips him the news. This starts a chain of events that eventually culminates in a meeting of SCDP's partners, blindsiding Roger, who has not told anybody about the break with Lucky Strike. Roger is forced to make a call to Lee; instead of talking to him directly, Roger fakes it by simply repeating his side of the conversation from his dinner with Lee. He is told by Cooper that he failed because he never took himself seriously, and neither did Lee. ("Chinese Wall")