Heyman was born in Santa Fe, New Mexico and grew up in Cedarhurst, New York He graduated from Northwestern University's Medill School of Journalism in 1983. He lived in Southern California in the 1980s writing for the "Daily Breeze."
Heyman began his professional career as a sports writer with The Daily Dispatch in Moline, Illinois.
Heyman spent 16 years at Newsday, where he served as the New York Yankees beat writer, baseball columnist and general sports columnist. In 1999 and 2000 Heyman was a baseball columnist for The Sporting News.
Heyman joined Sports Illustrated in July 2006. Heyman usually reported on baseball news year-round and wrote a baseball notes column called The Daily Scoop for SI.com, which appeared most weekdays during the baseball season and twice a week during the offseason. Heyman also frequently wrote the "Inside Baseball" column in the magazine.
In 2009 Heyman joined the recently launched MLB Network as a baseball insider.
In December 2011, it was announced that Heyman will be leaving Sports Illustrated to cover baseball for CBS Sports, following the 2011 MLB Winter Meetings.