[4] His father, Charles, was an optometrist and his British-born mother Patricia (d. 2014)[5] was a housewife who emigrated to the United States at age 14.

[7] Cowherd described himself as a loner during his childhood, spending much time sitting on his roof, listening to baseball games on the radio.

[10] Cowherd was roommates with football player and coach Jim McElwain at Eastern Washington University.

Cowherd began his career as the play-by-play voice for the San Diego Padres Triple-A affiliate Las Vegas Stars.

He eventually became a sports director at KVBC in Las Vegas, where he was named Nevada's Sportscaster of the Year five times.

[14] In 2003, Cowherd was selected to replace Tony Kornheiser for the late-morning time slot (10 AM – 1 PM ET) on ESPN Radio.

[17] In March 2018, Cowherd - who had previously referred to professional wrestling fans as "lonely, pathetic Booger Eaters"[18] - attended the taping of an episode of WWE SmackDown.

[19] On the April 5, 2007, edition of The Herd, Cowherd directed his listeners to "blow up" the sports blog The Big Lead by simultaneously visiting its home page.

ESPN's new Ombudsman, LeAnne Schreiber, wrote an article sharing her negative opinion of Cowherd's actions.

On July 23, 2015, Cowherd made remarks connecting the number of baseball players from the Dominican Republic to the game's alleged simplicity.

"[24][25] The remarks drew the ire of some Dominican players, such as José Bautista, and of the MLB Players Association; later that day, USA Today reported that the MLBPA was considering the possibility of "withholding cooperation" with ESPN and Fox over their lack of reaction to the remarks.

Major League Baseball also condemned Cowherd for making remarks they felt were "inappropriate, offensive and completely inconsistent with the values of our game.

[26] During the final episode of The Herd, Cowherd presented statistics from several studies regarding the current state of education in the Dominican Republic.

Network president John Skipper stated that Cowherd's presence had been "mutually beneficial", going on to say that "he came to national prominence on ESPN with his unique perspective on sports and society.

Although his contract was originally scheduled to end a week later on July 31, Cowherd was released earlier following controversial remarks he made regarding Dominican baseball players during the previous day's edition of The Herd.

[33] In 2018, Cowherd partnered with iHeartRadio and Red Seat Ventures to launch The Herd Podcast Network.