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Wilbon began working for The Washington Post in 1980 after summer internships at the newspaper in 1979 and 1980. He covered college sports, Major League Baseball, the National Football League and the National Basketball Association before being promoted to full-time columnist in 1990. 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.
In his career, Wilbon covered ten Summer and Winter Olympic Games for The Washington Post, every Super Bowl since 1987, nearly every Final Four since 1982 and each year's NBA Finals since 1987. Notably, he was also the only reporter based outside of Hawaii to cover the historic basketball upset of top-ranked Virginia by then-NAIA member Chaminade in 1982 (he was in Honolulu to cover a college football bowl game).
During his time at the Post, Wilbon earned the reputation as one of "the best deadline writer[s] in American newspapers." In 2001, Wilbon was named the top sports columnist by the Society of Professional Journalists.
In recent years, Wilbon has become more known as an ESPN personality than as a reporter. On December 7, 2010, he wrote his last column for the Washington Post and officially dedicated full-time to work for ESPN and ABC.
After contributing to ESPN's The Sports Reporters and other shows on the cable network, Wilbon began co-hosting ESPN's daily opinion forum Pardon the Interruption (PTI) with Tony Kornheiser on October 22, 2001. Wilbon was also a member of ABC's NBA Countdown (which he hosted with Jalen Rose, Bill Simmons and Magic Johnson), which was 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 Michael, USA Today basketball writer David Dupree and Tony Kornheiser on Full Court Press during the basketball season. Both of these shows were canceled in December 2008 due to budget cuts. 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.
In late 2006, Wilbon agreed to a multi-year contract extension with ESPN. 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. The network gained priority therein with regards to conflicts with his newspaper assignments. The first major conflict occurred on February 4, 2007, when Wilbon covered a Detroit Pistons–Cleveland Cavaliers game instead of Super Bowl XLI.