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 commentator and television personality recognized for his prominent roles on sports debate shows. He gained widespread recognition for his often controversial opinions and on-air debates with Stephen A. Smith on ESPN's First Take. After leaving ESPN in 2016, Bayless launched Skip and Shannon: Undisputed on Fox Sports 1 alongside Shannon Sharpe. He led Undisputed for eight years before his departure in August 2024. Bayless is known for his provocative style and passionate sports analysis.

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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, gaining experience in sports journalism.

August 1976: Joins Los Angeles Times

In August 1976, Skip Bayless took a position at the Los Angeles Times, where he wrote investigative stories, including those about the Los Angeles Dodgers and Rams.

1989: Joins The Sports Reporters on ESPN

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

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,' which focused on Tom Landry's Dallas Cowboys.

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

Check it on Amazon

1991: Hosts Radio Show for KLIF

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

1992: Member of NFL Prime Monday's 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: 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, after Cumulus Media bought KTCK, Skip Bayless's contract was bought out.

1998: Joins Chicago Tribune

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

1999: Commentator for Golf Channel

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

2000: Commentator 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 after being the lead sports columnist.

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', and made frequent appearances 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', and made frequent appearances 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 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 on 'Cold Pizza' for daily debate segments and to write columns for ESPN.com.

2004: Moves 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.

May 2007: Cold Pizza Rebranded as First Take

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