Will Cain is a columnist, conservative political analyst, and sports commentator. He has been a contributor for ESPN since March 2015,[2] working with the features unit and E:60 and appearing on First Take; he has also appeared on Outside the Lines and ESPN Radio.[3] He has been a contributor for The Blaze and CNN, appearing frequently on Soledad O'Brien's morning program Starting Point.

Cain previously worked as a fill-in host for CNN's In the Arena, where he co-hosted the program with E.D. Hill from February 28, 2011 to August 5, 2011.

He was previously a political commentator for several news networks and publications and has produced and directed the docuseries Alise vs The Mayor, a mini-series exposing New York City Mayor Bill de Blasio​’s attempts to curb charter schools.[32]

Cain began working as a radio personality as a fill in for ESPN Radio anchors. Cain then became cohost of The Ryen Russillo Show.[4] Cain began hosting his own radio show on ESPN Radio in 2018.[5]