Heyman began his professional career as a sports writer with The Daily Dispatch in Moline, Illinois.
In the Sports Illustrated magazine, Heyman frequently wrote an "Inside Baseball" column.
He and fellow New York Post baseball columnist Joel Sherman soon after launched a podcast entitled The Show.
In December 2022, Heyman infamously tweeted "Arson (sic) Judge appears headed to the Giants."
"[3] In a New York Post article published December 2023 addressing the conclusion of Shohei Ohtani free agency, Heyman made numerous controversial statements regarding the possibility of Ohtani signing in Toronto, including "...this is much better for Major League Baseball."