Will Cain is a columnist, conservative political analyst, and sports commentator. He has been a contributor for ESPN since March 2015,  working with the features unit and E:60 and appearing on First Take ; he has also appeared on Outside the Lines and ESPN Radio.  He has been a contributor for The Blaze and CNN , appearing frequently on Soledad O'Brien 's morning program Starting Point .
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. 
Cain is a graduate of Pepperdine University in Malibu, California , where he played Varsity Water Polo, and graduated with his J.D. from the University of Texas School of Law. He is a licensed attorney in Texas, but didn't any interest in practicing law. 
Will Cain developed a passion for media and newspapers after law school. When Will Cain's father died midway through 2001, he moved back to Texas to help take care of his younger brother. Around that time, he decided to become an entrepreneur and purchased two local community newspapers outside Dallas, Texas . His venture, eventually named Cain Communications, continued to grow and he started several more papers. He eventually sold off the entire group to Stevens Media. 
After that, Cain started a Hispanic media company called Quince Media. Named after the quinceañera (the 15th birthday celebration for a Hispanic girl), he published a magazine and website that developed a strong following.  The company eventually garnered Cain the accolade of 40 Most Influential People in the Magazine Industry by Folio in 2007.
After selling his second business, he wanted to get involved in debate and politics. As a result, Cain hosted the video interview series “Off the Page.”  On the program, he interviewed guests such as Arizona Senator Jon Kyl  and UN Ambassador John Bolton .  He also moderated debates between the National Review and The Nation .
Will was previously an analyst for The Blaze . While there, he provided commentary on the 2012 presidential election and other major political events. In 2015, he hosted a show called "The Cain Conversation," where he interviewed public figures to find out more about their stories. 
In addition to "The Cain Conversation," he hosted the shows Real News and Cain and Cupp . 
Will Cain joined ESPN in March 2015.  He auditioned to replace Skip Bayless as co-host of the show First Take on June 22, 2016.  In his audition, he criticized LeBron James ' grammar when he answered his critics after winning his third championship; many people found that to be in poor taste.  
Other TV Appearances