Following the death of his father in 2001, Cain returned to the Dallas area to help care for his younger brother. While in Texas, Cain bought two community newspapers and started others before selling them to
Stephens Media, publisher of the
Las Vegas Review-Journal. Cain then was named co-host of
The Ryen Russillo Show but Russillo soon left the show. Cain began hosting his own show,
The Will Cain Show, on ESPN Radio in 2018.
The Washington Post observed about Cain's ESPN presence in 2018: "Cain's growing profile comes amid consistent charges of liberal bias at ESPN for its coverage of social and political issues in sports." Cain continued to appear sporadically on
First Take until his final appearance on June 24, 2020, while his final episode of
The Will Cain Show aired two days later.
2020–present: Fox News In 2020, Cain left ESPN to move to Fox News as co-host of
Fox & Friends Weekend (along with
Jedediah Bila and
Pete Hegseth). His first appearance on
Fox & Friends Weekend was in August 2020. combining his commentary in news, politics, and sports. In addition to hosting
Fox & Friends Weekend, Cain serves as a regular fill-in host on programs such as
The Five and
Jesse Watters Primetime. In May 2023, Cain served as an interim host of
Fox News Tonight following the firing of
Tucker Carlson. On January 13, 2025, Fox News announced that he would become the permanent host of the network's 4 p.m. hour following the departure of long-time anchor
Neil Cavuto. Cain ended his run on
Fox & Friends Weekend on January 18 and
The Will Cain Show debuted on January 21, 2025. On September 10, 2025, Cain was tasked with reporting the confirmation of
Charlie Kirk's death following his
assassination at
Utah Valley University. Cain had hosted Kirk's final television interview on his show the previous day. ==Political commentary==