Career Timeline of Skip Bayless: Major Achievements and Milestones

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 recognized for his prominent roles on sports debate shows. He gained notoriety for his time on ESPN2's First Take with Stephen A. Smith. In September 2016, Bayless launched Skip and Shannon: Undisputed on Fox Sports 1 alongside Shannon Sharpe, which he hosted until August 2024. Bayless is known for his controversial and opinionated takes on various sports topics, making him a notable and often polarizing figure in sports media.

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Full Timeline Career & Achievements

1969: Internship at The Daily Oklahoman

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

August 1976: Joins Los Angeles Times

In August 1976, Skip Bayless took a position at the Los Angeles Times, where he became known for his investigative stories.

1989: Joins The Sports Reporters

In 1989, Skip Bayless joined host Dick Schaap as a panelist on ESPN's "The Sports Reporters."

1989: Publishes 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 Dallas Cowboys.

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

Check it on Amazon

1991: Hosts Radio Show on KLIF

In 1991, Skip Bayless began hosting a sports talk radio show on Dallas radio station KLIF.

1992: Member of NFL Prime Monday's Debate Team

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

1993: Publishes 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.

1996: Leaves KTCK

In 1996, Skip Bayless's contract with Fort Worth radio station KTCK ("the Ticket") was bought out by Cumulus Media after they purchased the station.

1998: Joins Chicago Tribune

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

1999: Commentary for the Golf Channel

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

2000: Commentary for the 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 and The Best Damn Sports Show Period

In 2001, 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.

2001: Guest Host on The Jim Rome Show

In 2001, Skip Bayless became the primary guest host of the syndicated radio program, "The Jim Rome Show."

2002: Appears on Jim Rome's show and The Best Damn Sports Show Period

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 and SportsCenter

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: Hired Full-Time by ESPN

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

2004: Moves Full-Time to Television

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

May 2007: Cold Pizza Rebranded as First Take

In May 2007, Cold Pizza, which had been produced in New York, was rebranded as First Take and moved to ESPN's headquarters in Bristol, Connecticut. Around this time, Skip Bayless stopped writing for ESPN.com.

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 Announced

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.