[4][6] His column in the Post, which dealt as much with the culture of sports as the action on the court or field, appeared up to four times a week until he left to work full-time for ESPN on December 7, 2010.

[citation needed] On December 7, 2010, he wrote his last column for The Washington Post and officially dedicated full-time to work for ESPN and ABC.

One memorable segment had Wilbon taking issue with Brian Williams (née Bison Dele) transferring from Maryland to Arizona.

[11] Wilbon also forged a close friendship with former Marshall and former NFL quarterback Byron Leftwich while the young passer was a standout player for HD Woodson in Washington, D.C.

After accepting the contract, Wilbon offered to resign from the Post, but the newspaper's chairman Don Graham and executive editor Len Downie both asked him to stay on.

[23] On August 10, 2008, during a Cubs–Cardinals game at Wrigley Field, Wilbon threw out the ceremonial first pitch and then sang "Take Me Out to the Ballgame" as part of the seventh-inning stretch.

Footage of Wilbon wearing a tucked-in Cubs jersey and bouncing the pitch is frequently shown on Pardon The Interruption as a friendly teasing by Kornheiser.

On July 12, 2013, Wilbon, Kornheiser and Tony Reali (PTI statistician and de facto co-host) were guests at the White House.