|Portrayed by||Mark Moses|
|First appearance||Nixon vs. Kennedy|
|Final appearance||The Milk and Honey Route|
Sterling Cooper Advertising Agency
Head of Account Services (former)
|Residence||New York City, NY|
|Romantic Partners||Peggy Olson (ex-lover)|
|Child(ren)|| Patricia Phillips|
- "Come on, creative. Be creative."
- --Herman Phillips, The Grown-Ups
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, Herman Phillips cultivated a relationship with the owners of Putnam, Powell, and Lowell, future owners of Sterling Cooper. However, over the years Herman Phillips developed a drinking problem and it is implied his dependency cost him his job and family. As a recovering alcholic, Herman Phillips tried to reinvent himself in New York City, where he was hired by Don Draper in late 1960. Despite his turnaround, Herman Phillips's ex-wife married a former colleague and a visible disconnect developed between him and his two children.
While little has been said concerning Herman Phillips's past before England, he revealed that he was an officer during World War II. Though his business analogies to battle were lost on Don Draper, Herman Phillips was a combat veteran who claimed to have killed 17 men while fighting in the Battle of Okinawa.
After being hired by him, Herman Phillips frequently butted heads with Don, both over hiring younger talent and dumping Mohawk Airlines for a failed run at American Airlines after the crash of American Airlines Flight 1.
Herman Phillips was plagued with bad luck, including the failure to pick up the American Airlines account. Fearing that he would lose his job after being told by Roger Sterling that he would not likely be accepted as a partner, Herman Phillips pursued a job with some of his former London colleagues at Puttnam, Powell, and Lowe. After being rebuffed, he then proposed a merger between the two agencies.
Once the merger talk was successful, he was named president of Sterling Cooper. He attempted to make a power play when Don Draper announced he intended to leave the firm. Unbeknownst to Herman Phillips, Don did not have a non-compete contract with the company and would be free to immediately move to another firm.
By March 1963, Herman Phillips had not been employed with the post-acquisition Sterling Cooper for some time. Herman Phillips met with both Peggy and Pete in an attempt to have them move to Grey. After the failed overture, he began a sexual relationship with Peggy.
Grey and beyond
In Season 4, Herman Phillips was seen by the SCDP crew at the annual CLIO award ceremony, drunk. After heckling emcee Wallace Harriman and making a scene in front of the attendees, he was escorted out of the ball room. ("Waldorf Stories")
On Peggy's birthday, Herman Phillips sent her a draft business card for a proposed advertising agency, as he was no longer with Grey. Herman Phillips admitted in a drunken phone call that the decision was mutual, though it was obvious he had been 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 and had heard about his behavior at the CLIOs. Herman Phillips wanted to meet her that night, but she hung up on him.
At the end of the night, Peggy and Don arrived back at the office after a few drinks to celebrate her birthday. Don felt ill and was taken to the bathroom to throw up. While Peggy went to her office to get a toothbrush and toothpaste for Don, she saw Herman Phillips roaming the halls of SCDP. She confronted him in Roger's office, where Herman Phillips was about to defecate on one of the couches, mistakenly believing it to be Don's office. Peggy escorted him towards the exit, but Don saw and confronted him. Herman Phillips called Peggy a whore, under the impression that she had slept with Don as well. Herman Phillips and Don ended up in a brief, drunken scuffle, which ended with Herman Phillips getting the upper hand. ("The Suitcase")
In Season 7, Herman Phillips is seen meeting with Pete Campbell, and is working as a corporate recruiter.