Milch graduated summa cum laude from Yale where he won the Tinker Prize in English and was a member of the Delta Kappa Epsilon chapter, along with future U.S. president George W. Bush. He earned an MFA from the Iowa Writers' Workshop at the University of Iowa.
 To avoid the draft during the Vietnam War, Milch enrolled in Yale Law School, but was expelled for shooting out a police car siren with a shotgun. Milch then worked as a writing teacher and lecturer in English literature at Yale. During his teaching career, he assisted Robert Penn Warren and Cleanth Brooks in the writing of several college textbooks on literature. Milch's poetry and fiction have been published in The Atlantic Monthly and the Southern Review.
 In 1982, Milch wrote a script for Hill Street Blues which became the episode "Trial by Fury". This began his career in television. He worked five seasons on Hill Street Blues as executive story editor and then as executive producer. Milch earned two more Writers Guild