Phil, played by Ryan Woodle, is a salesman at the Chicago branch of the Farrady Electric Iron company.
He wins the annual sales competition for 1922 and celebrates New Year's Eve with his colleagues at an office party. He mocks George Mueller when he returns with enough sales to win, but after the deadline. ("Resolution")
The salesmen play a prank on Mueller, covering his face and shirt with ink from a gag pen. He is mortified and tries to hide from their boss, Scotty Gulliver. When Van Alden returns to work the next day his colleagues brush off the prank as an initiation. They invite him for a drink at Herkemeyer's speakeasy. The evening sours when the venue is raided by Prohibition Agents. ("Bone for Tuna")
Phil continues his bullying of Van Alden, and, during a sales pitch practice of the new steam iron, relentless mocks him, eventually provoking Van Alden into pressing the iron against his face. Several months later, Phil, Ralph, and Scotty Guliver track him down to take revenge and are beating him, Van Alden draws a gun and shoots them all dead.
- Scotty Gulliver: Uncle and boss (deceased)
- Ralph: Colleague (deceased)
- Hank: Colleague
- Mary: Colleague
- George Mueller: Colleague, murderer (deceased)
- "If you screw as poorly as you pitch you really should be selling dildos because your wife could use..."
|Season three appearances|
|"Resolution"||"Spaghetti and Coffee"||"Bone for Tuna"||"Blue Bell Boy"|
|"You'd Be Surprised"||"Ging Gang Goolie"||"Sunday Best"||"The Pony"|
|"The Milkmaid's Lot"||"A Man, A Plan..."||"Two Imposters"||"Margate Sands"|
|Season four appearances|
|"New York Sour"||"Resignation"||"Acres of Diamonds"||"All In"|
|"Erlkonig"||"The North Star"||"William Wilson"||"The Old Ship of Zion"|
|"Marriage and Hunting"||"White Horse Pike"||"Havre De Grace"||"Farewell Daddy Blues"|