Before this all started, Henry was a journalist whose work has appeared in HOOP, Inside Stuff, Men's Journal, the official NBA Finals program, and on CBS's national radio network. Henry wrote more than a dozen cover stories, more than a hundred feature articles, and a regular column. He has discussed sports on the air as a guest of various national and local television and radio programs.
Before becoming a full-time writer in 1998, Henry won awards as a radio reporter for CBS radio affiliate WIBA. He also wrote a number of cover stories for the Madison, WI-based weekly Isthmus. His writing and research have been featured in award-winning documentaries.