Career Timeline of Skip Bayless: Major Achievements and Milestones

By Popular Timelines Editorial Team · Updated: April 19, 2026

How Skip Bayless built a successful career. Explore key moments that defined the journey.

Skip Bayless is an American sports columnist, commentator, and television personality known for his role on ESPN2's First Take with Stephen A. Smith and his show Skip and Shannon: Undisputed with Shannon Sharpe on Fox Sports 1. He is recognized for his often controversial and provocative opinions on sports topics, contributing to his fame and notoriety in the sports media landscape. He left First Take in June 2016 and Undisputed in August 2024.

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Full Timeline Career & Achievements

1969: Internship at The Daily Oklahoman

During the summer of 1969, Skip Bayless interned under sports editor Frank Boggs at The Daily Oklahoman.

August 1976: Joins Los Angeles Times

In August 1976, Skip Bayless took a position at the Los Angeles Times, where he became known for investigative stories on the Los Angeles Dodgers and Rams owner Carroll Rosenbloom.

1989: Joins The Sports Reporters

In 1989, Skip Bayless joined host Dick Schaap as a panelist on ESPN's The Sports Reporters and was a regular on the Sunday morning show for the next decade.

1989: Publication of God's Coach

In 1989, Skip Bayless wrote his first book, God's Coach: The Hymns, Hype and Hypocrisy of Tom Landry's Cowboys, about the rise and fall of Tom Landry's Dallas Cowboys.

God's Coach: The Hymns, Hype, and Hypocrisy of Tom Landry's Cowboys

Check it on Amazon

1991: Hosts Sports Talk Radio Show

In 1991, Skip Bayless began hosting a sports talk radio show from 6–8 p.m. Monday through Friday for Dallas radio station KLIF.

1992: Member of Knights of the Roundtable

In 1992, Skip Bayless became a member of the original debate team on NFL Prime Monday's "Knights of the Roundtable" segments with Mitch Albom and Michael Wilbon.

1993: Publication of The Boys

In 1993, following the Cowboys' Super Bowl victory, Skip Bayless wrote The Boys: The Untold Story of the Dallas Cowboys' Season on the Edge.

1994: Investor in KTCK and Host of The Skip Bayless Show

In 1994, Skip Bayless became one of the original investors in the Fort Worth radio station KTCK ("the Ticket"), and hosted The Skip Bayless Show from 6–9 a.m. weekdays.

1996: Sale of KTCK and End of Contract

In 1996, the original owners sold KTCK to Cumulus Media, which bought out Skip Bayless's contract. He was also a frequent guest on ESPN Radio's first national weekday show, The Fabulous Sports Babe.

1998: Joins Chicago Tribune

In 1998, Skip Bayless left Dallas after 17 years and became the lead sports columnist for the Chicago Tribune.

1999: Commentary for Golf Channel

In 1999, Skip Bayless provided commentary for the Golf Channel from the major golf championships.

2000: Commentary for Golf Channel

In 2000, Skip Bayless provided commentary for the Golf Channel from the major golf championships.

July 2001: Leaves Chicago Tribune

In July 2001, Skip Bayless left the Chicago Tribune.

2001: Appears on Jim Rome's show on Fox Sports Net

In 2001, Skip Bayless appeared regularly on Jim Rome's show on Fox Sports Net, The Last Word. He also made frequent appearances on Fox's The Best Damn Sports Show Period during the same period.

2001: Guest Host of The Jim Rome Show

In 2001, Skip Bayless became the primary guest host of the syndicated radio program, The Jim Rome Show. He also began making regular appearances on Chet Coppock's show on the Sporting News Radio network, Coppock On Sports.

2002: Appearances on Fox Sports Net

In 2002, Skip Bayless appeared regularly on Jim Rome's show on Fox Sports Net, The Last Word. He also made frequent appearances during the same period of time on Fox's The Best Damn Sports Show Period.

2003: Becomes a fixture on Rome is Burning

In 2003, when Jim Rome moved to ESPN, Skip Bayless became a fixture on Rome is Burning. He was also featured in a weekly Sunday morning SportsCenter debate segment with Stephen A. Smith, "Old School/Nu Skool".

2004: Full-Time Hire by ESPN

In 2004, ESPN hired Skip Bayless full-time to team up with Woody Paige on ESPN2's Cold Pizza for daily debate segments called "1st and 10", and to write columns for ESPN.com.

2004: Move to Television Full-Time

In 2004, Skip Bayless moved full-time into television, after co-hosting a weekend show on ESPN Radio with Larry Beil until then.

2006: Cameo Role in Rocky Balboa

In 2006, Skip Bayless, along with ESPN colleagues Woody Paige and Jay Crawford, had a cameo role in the film Rocky Balboa, discussing a possible fight between Rocky and Mason Dixon on their "First and 10" segment. Bayless stated that Balboa "was completely overrated".

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May 2007: Cold Pizza Rebranded as First Take

In May 2007, the show Cold Pizza, where Skip Bayless was a debater, was rebranded as First Take, and production was moved to the network's headquarters in Bristol, Connecticut. Around this time, Bayless stopped writing for ESPN.com.

2010: Appearance in Pony Excess

In 2010, Skip Bayless appeared in the ESPN 30 for 30 film, Pony Excess, about the Southern Methodist University football scandal. Bayless covered the Mustangs while writing for both The Dallas Morning News and the Dallas Times Herald.

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2011: Appearance in Herschel

In 2011, Skip Bayless appeared in the ESPNU documentary, Herschel, about University of Georgia running back Herschel Walker.

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August 2012: Resumes Writing for ESPN.com

In August 2012, Skip Bayless resumed writing columns for ESPN.com.

April 26, 2016: Parting ways with ESPN

On April 26, 2016, it was reported that Skip Bayless had parted ways with ESPN, and would be moving to Fox Sports after his contract expired in August.