While beginning his law practice, Crawford worked for Democratic candidates John Glenn and Walter Mondale. In 1982, he was an unsuccessful candidate for Florida's state legislature as a Democrat. Crawford joined the staff of the "Orlando Sentinel" in 1985 as a legal affairs and politics reporter. In 1989, he moved to the paper's Washington bureau. In 1997, Crawford left the Sentinel to run The Hotline until 2003, when he joined "Congressional Quarterly" leading to his work for NBC, CNBC and MSNBC.