He was born in Washington, D.C. and raised in Hyattsville, Maryland, and started his career in journalism as a city side reporter at The Boston Globe newspaper. In 1983, he wrote for The Chicago Reporter, a monthly investigative magazine on Chicago's racial and social issues. In 1986, Blackistone joined The Dallas Morning News newspaper as a reporter in the City section; he later moved to the Business section covering economics, and the Metropolitan section covering city events and issues.
After covering Nelson Mandela's U.S. tour in 1990, he moved to SportsDay to cover sports business and write columns. A year later, he became a full-time SportsDay columnist.
In September 2006, Blackistone was one of 111 journalists to accept a buyout offer from The News, forcing his departure from the newspaper on September 15, 2006.
He is a former reporter and columnist for The Dallas Morning News from 1986 to 2006, and was a regular panelist for ESPN's Around The Horn.