|Herman 'Duck' Phillips|
|Portrayed by||Mark Moses|
|First appearance||Nixon vs. Kennedy|
|Final appearance||The Suitcase (Last seen)|
Sterling Cooper Advertising Agency
Head of Account Services (former)
|Residence||New York City, NY|
|Romantic Partners||Peggy Olson (ex-lover)|
- "Come on, creative. Be creative."
- -Duck Phillips, The Mountain King
Herman "Duck" Phillips was the Head of Account Services at Sterling Cooper advertising agency from late 1960 until at least October of 1962. Originally an ad man in England, Duck cultivated a relationship with the owners of Putnam, Powell, and Lowell, future owners of Sterling Cooper. However, over the years Duck developed a drinking problem and it is implied his dependency cost him his job and family. As a recovering alcholic, Duck tried to reinvent himself in New York City, where he was hired by Don Draper in late 1960. Despite his turnaround, Duck's wife marries a former colleague and a visible disconnect remains with regards to his two children.
While little has been said concerning Duck's past before England, he reveals he was an officer during World War II. Though his business analogies to battle are lost on Don Draper, Duck was a combat veteran who claims to have killed 17 men while fighting in the Battle of Okinawa.
Duck is plagued with bad luck, between the failure to pick up the American Airlines account, to disasters with advertising agencies that clients were not interested in. Fearing that he would lose his job, Duck pursued a merger with some of his former London colleagues at Puttnam, Powell, and Lowe. Once the merger was successful he was named president of Sterling Cooper. He attempts to make a power play when Draper announces he intends to leave the firm, unknown to him that Draper does not have a non-compete contract with the company and would be free to immediately move to another firm.
By March 1963, Duck had not been employed with the new Sterling Cooper for some time. Duck meets with both Peggy and Pete in an attempt to have them move to Grey. After being approached, he begins a sexual relationship with Peggy.
Grey and beyond
Duck was seen by the SCDP crew at the annual CLIO award ceremony, drunk. After heckling emcee Wallace Harriman and making a disruption in front of the attendees, he was escorted out of the ball room.
Duck sent Peggy a birthday present, a business card reading Phillips-Olson Advertising. Slightly stunned, she wonders why he was calling. Duck admits that the decision was mutual, though it was obvious he was fired. He tried to persuade her with Tampax, which he had quiet discussions with. Peggy was not sure if he was serious about the offer after hearing about the CLIOs. Duck wants to meet her tonight, though she hangs up on him.
At the end of the night, Peggy and Don arrive back at the office after a few drinks to celebrate her birthday. Don feels ill and is taken to the bathroom to throw up. While Peggy goes to her office to get a toothbrush and toothpaste for Don, she sees Duck roaming the halls of SCDP. She confronts him in Rogers office, about to defecate on one of his couches, mistakenly believing it to be Don's office. Peggy escorted him towards the exit, but Don saw him and confronted him. Duck called Peggy a whore, under the impression that she slept with Don as well. They get into a scuffle, but it ends shortly thereafter.