[8] Born in Milwaukee, Wisconsin, Milkowski studied journalism in college, earning a bachelor's degree in 1977 from the University of Wisconsin-Milwaukee, where he also served as editor of the campus newspaper, The UWM Post.

He moved to New York in September 1980 after accepting a position as managing editor for the Long Island-based weekly entertainment publication Good Times, where he worked for two years.

[1][2] As a New York-based freelance music writer from 1983 to 1993, Milkowski contributed cover stories, interviews, record reviews, and opinion pieces on jazz, rock, and blues musicians for numerous national magazines.

In September 1993, he moved to New Orleans, where he continued freelancing for several national music magazines while also appearing weekly as an overnight DJ ("The Milkman") at radio station WWOZ.His first book, JACO: The Extraordinary and Tragic Life of Jaco Pastorius, The World's Greatest Bass Player (Miller-Freeman Books) was published in April 1995 during the week of the birth of his daughter.

[10] As a record producer, Milkowski oversaw recordings for guitarist Phil deGruy (Innuendo Out the Other, NYC, 1995), guitarist Pat Martino (All Sides Now, Blue Note, 1998) and produced the compilation Come Together: A Guitar Tribute to The Beatles (NYC, 1993) as well as tracks on the compilations World Christmas (Metro Blue, 1996) and Who Loves You: A Tribute to Jaco Pastorius (JVC, 2001).