In 1980, Wilbon began working for The Washington Post after summer internships at the newspaper in 1979 and 1980. He covered college sports, Major League Baseball, the NFL and the NBA before being promoted to full-time columnist in February 1990.
In his career, Wilbon has covered several different Summer and Winter Olympic Games for The Washington Post, and almost every Super Bowl, Final Four, and NBA Finals since 1987.
After contributing to ESPN's The Sports Reporters and other shows on the cable network, he began co-hosting ESPN's daily Pardon the Interruption, or PTI as it is known among its fans, with Tony Kornheiser on October 22, 2001. He has been a member of ABC's "NBA Countdown," which is the pre-game show for the network's NBA telecasts.
In addition to his work at The Washington Post, PTI and ESPN, Wilbon appeared weekly on WRC-TV in Washington, D.C. with WRC Sports Director George Michael, and Pro Football Hall of Famers John Riggins and Sonny Jurgensen on Redskins Report during the football season. He also appeared with USA Today basketball writer David DuPree and Tony Kornheiser on Full Court Press during the basketball season.
In 2001 Wilbon was named the top sports columnist by the Society of Professional Journalists. On December 10, 2010, Wilbon wrote his last article for the Washington Post, and dedicated his full time to ESPN.