Herman Phillips

Herman 'Duck' Phillips
Portrayed by	Mark Moses
First appearance	Nixon vs. Kennedy
Final appearance	In Care Of (Last seen)
Details
Gender	Male
Occupation	Grey Sterling Cooper Advertising Agency Head of Account Services (former)
Residence	New York City, NY
Relations
Ex-Wife	Pauline Phillips
Romantic Partners	Peggy Olson (ex-lover)
Child(ren)	Patricia Phillips Mark Phillips

"Come on, creative. Be creative."

-Duck 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, 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 ex-wife married a former colleague and a visible disconnect developed between him and his two children.

While little has been said concerning Duck'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, Duck was a combat veteran who claimed to have killed 17 men while fighting in the Battle of Okinawa.

Sterling Cooper

After being hired by him, Duck 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.

Duck 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, Duck 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 Duck, Don did 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 post-acquisition Sterling Cooper for some time. Duck 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 5, Duck 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.

On Peggy's birthday, Duck sent her a draft business card for a proposed advertising agency, as he was no longer with Grey.  Duck 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. Duck 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 Duck roaming the halls of SCDP.  She confronted him in Roger's office, where Duck 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.  Duck called Peggy a whore, under the impression that she had slept with Don as well. Duck and Don ended up in a brief, drunken scuffle, which ended with Duck getting the upper hand.

In Season 7, Duck is seen meeting with Pete Campbell.  Now sober, Duck is working as a corporate recruiter.