Wolff joined MSNBC in 2005 as Executive Producer, “The Situation with Tucker Carlson.” Before joining MSNBC, Wolff was Creator, Executive Producer, and On-air Contributor to Fox Sports Network's daily talk show "I,Max." Wolff was previously Creator of ESPN's "Around the Horn."
From 1998 to 2002, Wolff wrote screenplays for Scott Rudin at Paramount Pictures, for Dimension Films, and for Dreamworks, including "Rebound," a feature film released by Fox in July, 2005.
Before his writing career, Wolff worked for ESPN as a production assistant, associate producer, and Los Angeles bureau producer. He worked for the network's "SportsCenter," "Outside the Lines," "NFL Countdown," and "College Football Gameday" programs. His first job in television was an internship at KSDK, the NBC affiliate in his hometown, St. Louis, Missouri .
Wolff graduated with honors from Harvard College and resides in New York City with his wife Alison Stewart and their son.