Whitlock played Division I college football at Ball State as an offensive lineman.

Whitlock had guest-hosted several ESPN TV shows, including Jim Rome Is Burning, and Pardon the Interruption.

In 2006, Whitlock announced the departure of his online column from ESPN.com's Page 2 in favor of AOL Sports, but initially expected to continue his television work for ESPN.

However, after the announcement, Whitlock was interviewed by sports blog The Big Lead, and disparaged two of his ESPN colleagues.

He soon announced to The Kansas City Star readers in September 2006 that he was fired altogether from ESPN as a result of his remarks; he wrote that the company doesn't tolerate criticism and acted as they saw fit.

On February 10, 2012, in the middle of the Knicks' 92–85 victory over the Los Angeles Lakers, with Jeremy Lin scoring a career-high 38 points, Whitlock posted on Twitter, stating that "some lucky lady in NYC is gonna feel a couple inches of pain tonight.

"[7] Silvie Kim wrote in Hyphen that Whitlock "reinforced the insipid and insidious 'small Asian penis' stereotype.

In response, Whitlock wrote that he'd been trying too hard to be a comedian, adding "I debased a feel-good sports moment.

After over a year and a half of delays, ESPN announced that Whitlock would no longer serve as the editor in chief for The Undefeated, and he was replaced on an interim basis by Leon Carter, the editorial director for the site.

On June 1, 2020, it was announced that Fox would not renew Whitlock's contract after the two sides couldn't come to an agreement.

In the June 2008 issue of Playboy, he wrote a 5,000-word column questioning America's incarceration and drug-war policies.

[28] In December 2023, Whitlock expressed a dislike of the Nineteenth Amendment and said that granting suffrage to women destroyed the principle of "one vote per household", which he associates with a time when American culture more strongly valued the family unit.