It’s hard to imagine a time when Skip Bayless wasn’t on television. His career, in fact, flourished way before he became a TV success. Bayless showed us exactly what it means to be celebrated and controversial at the same time. He’s the type to never hold back—a quality that has been his bread and butter throughout his entire career. Now that the sports industry is finally back on again, Skip Bayless is back at acting as well. His various recent comments—from insulting Tom Brady to poking on Dak Prescott’s mental health illness—have caused quite a stir. But then again, that’s precisely why his net worth is at $13 million today. Here’s a closer look into how Bayless achieved his success and how it all amounted to $13 million so far.
Born on December 4, 1951, John Edward Bayless II is an Oklahoma City native. He comes from a successful background with his parents owning and running a local barbecue restaurant, Hickory House. Bayless didn’t have any interest in pursuing the family culinary business, but his brother certainly did—famed restaurateur and celebrity chef Rick Bayless. The name “Skip” was a nickname given to him by his father simply out of affection. His father also addressed his mother the same name, which was short for “skipper of the ship.” Skip Bayless’ parents never called him by his real name, John. It wasn’t a bother to him, and Bayless actually got his name officially changed to Skip when he became an adult.
As a child, he found interest in sports as an athlete. He played both basketball and baseball throughout his high school years, and he also ended up writing the sports column for the school paper. Bayless was given a scholarship to attend Vanderbilt University, where he received his Bachelor of Arts degrees in both English and History in 1974. During his time at Vanderbilt, he became sports editor of the university student paper, and he also interned at the largest daily newspaper in the Oklahoma metro area.
Right after college, Bayless went to South Florida to work for The Miami Herald. Bayless didn’t stay in Miami for long, as he moved to Los Angeles in 1976 to work for the Los Angeles Times. He wrote sports news for both papers; and by the time he was 26 years old, he won his first award—the Eclipse Award for Outstanding Newspaper Writing in 1977. Around this time, Bayless moved yet again to another city and another newspaper, the Dallas Times Herald. During his work there, Bayless yet again won several awards for his achievements in sports journalism.
Bayless stayed in Dallas for 17 years before moving on to become lead sports columnist for the Chicago Tribune, where he also won a few awards for his work. He stayed there for about 3 years before focusing on his other media ventures. Throughout his career in print journalism, Bayless’ work also appeared in many sports publications, including Sports Illustrated.
Apart from his work as a print journalist, Bayless is also a published author. He published three books in the 90s, all of which were about the Dallas Cowboys. The three books he published met incredible criticsm, as they somewhat attacked the sports team of his city. Bayless has long been known to be a fan of the Cowboys’ previous quarterback, Tony Romo. But he’s actually getting heat again for his recent comments on the team’s current QB, Prescott.
Bayless started doing radio work in 1991 for a local Dallas radio station KLIF. From 1994-1996, he hosted his own show for a new Ft. Worth radio station that he was also part investor in. Around this time, he became a regular guest on ESPN’s first national weekday show, the beginning of a long relationship with the popular sports network.In 2001, Bayless co-hosted a weekend show on ESPN Radio, a position he held until 2004.
Bayless didn’t wait until 2004 to start appearing on TV. In fact, he had begun making television appearances as early as 1989, while he was still working for the Dallas Times Herald. He worked for a few ESPN programs in various roles—as panelist, morning show host, and member of debates teams. From 1999 to 2000, Bayless provided commentary for the Golf Channel.
In 2001, Bayless began to make appearances on various Fox Sports programs. During this time until 2016, Bayless would appear on various ESPN and ESPN2 programs including SportsCenter and Cold Pizza. Some of the segments that he’s mos known for include Old School/Nu School, 1stand 10, and First Take. Bayless left ESPN in 2016 and transferred over to Fox Sports 1.
Since 2016, Bayless has been host of the Fox Sports show along with Shannon Sharpe called Skip and Shannon: Undisputed. To this day, he’s still known, hated, and loved for his sharp commentary and no holds barred style.
Bayless has made a fortune for his talents in sports writing and sports commentary. He has appeared in so many media outlets including print, radio, and television. In addition, Bayless has appeared in a major motion film and a couple of documentaries. Bayless had a cameo role in the 2006 boxing film Rocky Balboa. In 2010 and 2011, he appeared on a couple of ESPN documentaries, one for the 30 for 30 series and another called Herschel.
Bayless’ career is a hallmark of success in sports and sports entertainment. He continues to shock us all and equally challenge the conventional views in the sports industry. It’s the force behind his successful career that have netted up to $13 million today. There are few careers like his in the industry, and we doubt there’ll be another one like it anytime soon.