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From 2000–2013, Whitaker worked as a writer and editor for SLAM Magazine, a hip-hop-influenced basketball magazine.
In summer 2004, Whitaker began to write weekly columns for SI.com, the official Sports Illustrated website.
He attended the University of Georgia and has written for magazines, newspapers and made guest appearances on television. He lives in New York with his wife and their dog Starbury, who is named after former New York Knicks point guard Stephon Marbury. He is an avid fan of Atlanta's three major professional sports franchises: basketball's Atlanta Hawks, baseball's Atlanta Braves, and football's Atlanta Falcons as well as English soccer team Manchester United.
In 2007, Whitaker won the NBA Blogger Awards' Lifetime Achievement Award for his work on "The Links" on SLAMonline.com. From 2006–2008, Whitaker was the editor-in-chief of Striker, an American soccer magazine. From 2008–10, Whitaker wrote a weekly column for Hawks.com, the official site of the Atlanta Hawks. During the 2008–09 NBA season, he did color commentary on several radio broadcasts of Hawks games. Whitaker has also been written about in The New Yorker and The New York Times. He recently appeared as a cultural commenter on VH1's series "I Love the New Millennium." Since 2008, he has been a regular contributor on NBA TV.
In 2010, he was one of the co-authors of the book "FreeDarko Presents: The Undisputed Guide to Pro Basketball History."
His memoir about growing up as a fan of the Atlanta Braves and Bobby Cox, titled "In the Time of Bobby Cox: The Atlanta Braves, Their Manager, My Couch, Two Decades, and Me," was released in March 2011, from Scribner.
From 2011–2013, he was GQ's NBA writer for GQ.com.
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