Feinstein is a columnist for the Washington Post, an author, a guest commentator on NPR, and does color commentary for United States Naval Academy football games. He is also a frequent contributor to PTI and The Jim Rome Show.

Feinstein was a sports writer for the The Chronicle while enrolled at Duke University, where he graduated in 1977. He made his name as a prominent author with A Season on the Brink (1987), a book documenting a season with the Indiana University basketball team and controversial coach Bob Knight. Feinstein has now written 23 books, including various best sellers on sports such as basketball, football, and golf. Other notable titles include A Good Walk Spoiled (1993), A March to Madness (1998), The Punch (2002), and Next Man Up (2005).