Before he began working at Slate, he covered politics for Time magazine for 12 years and was a White House Correspondent for the final four years. Dickerson graduated from the University of Virginia. He is the son of journalist Nancy Dickerson and wrote a book about their relationship titled On Her Trail. He also authored the book Whistlestop: My Favorite Stories from the Presidential Campaign History. He co-wrote the article “A War on Wilson?” for Time which was related to CIA leaks.