The Highs and Lows Of Skip Bayless’ Media Career

Skip Bayless’ style on morning sports talk shows epitomizes the saying “come strong or don’t come at all.” Anyone who has watched him on these programs knows Bayless isn’t going to have a lukewarm opinion on any topic that’s discussed. This has made him a polarizing figure, something that he’s been for many decades.

John Edward Bayless II was born in December 1951, and gives the credit for his success to his mother, Levita. Bayless has a brother, Rick, who has become a Michelin star chef in his own right. In a self-written piece on FOX Sports, Skip Bayless discusses sports as his saving grace in a household that had its fair share of turbulence.

By the 1990’s, Bayless had rose to prominence as a journalist in Dallas, and was at the right place at the right time to cover the dynastic Cowboys. He wrote a book called “Hell-Bent”, where he insinuated that Dallas quarterback Troy Aikman was gay. This infuriated the signal caller, who lashed out at Bayless as lacking credibility or respect by spreading false claims.

For better or for worse, Bayless has always had a high opinion of himself. The Dallas Times Herald went out of business in 1991, and the writer knew he had to find another source of income quickly. He began faxing his sports columns to interested readers for $99 annually according to The Ringer, which was an idea that was ahead of its time.

Before he became a hot take talking head, Bayless didn’t always to go the extreme when he was on television. He would often appear on shows with the more mild-mannered Mitch Albom and Mike Wilbon to discuss current sports events and put them into thoughtful context. That would change, however, in the early 2000’s.

ESPN took a stab at creating sports morning content that fans could easily digest. When Bayless first appeared on Cold Pizza, it had some debate elements but wasn’t primarily focused on blood-pumping arguments. Over time, it evolved into First Take, and Bayless would go full throttle with his strong opinions against the likes of Stephen A. Smith.

Bayless has been a notorious critic of NBA star LeBron James, regardless of the personal and team accomplishments he’s achieved. Perhaps this view is guided by Bayless’ up close and person coverage of Michael Jordan back in the 1990’s, but sports fans are well aware of the lengths he’s willing to go to speak ill of James.

Despite the Aikman controversy, Bayless has remained a staunch supporter of the Dallas Cowboys. He’s instead focused his animus on players across the NFL, by slightly changing their name to reflect a less respectable persona. He would often call Green Bay Packers kicker Mason Crosby 'Mason Crossbar', even though he made several clutch field goals in his career.

The First Take stage appeared to be too small for the egos of Smith and Bayless, so the latter left ESPN for FOX Sports. Bayless would star in his own debate show called Undisputed. His main sparring partner was Shannon Sharpe, who since left the show to join Smith at ESPN. Bayless now regularly debates former NFL players Richard Sherman, Keyshawn Johnson and Michael Irvin.