Sugar worked in advertising, including with the McCann Erickson agency. He was Publisher-Editor of Baseball Monthly magazine in 1962. Sugar bought Boxing Illustrated magazine in 1969 and was editor until 1973. From 1979 to 1983 he was editor and publisher of The Ring magazine. In 1988 he again became editor of Boxing Illustrated. In 1998 he founded Bert Sugar's Fight Game.

Sugar wrote more than 80 books, focusing on his favorite sports of boxing and baseball. Among his boxing books are Great Fights, Bert Sugar on Boxing, 100 Years of Boxing, Sting like a Bee (with José Torres), The Ageless Warrior (Preface, with Mike Fitzgerald) and Boxing's Greatest Fighters. Sugar was ranked as "The Greatest Boxing Writer of the 20th Century" by the International Veterans Boxing Association.

In May 2009 Sugar published Bert Sugar's Baseball Hall of Fame: A Living History of America's Greatest Game through Running Press.

With James Randi, Sugar co-wrote a book about Harry Houdini titled Houdini, His Life and Art.

Along with Lou Albano, he helped write The Complete Idiot's Guide to Pro Wrestling. He wrote a regular sports column for Smoke Magazine, a quarterly cigar lifestyle magazine. Sugar was described by sportscaster Bob Costas as being "Runyonesque" (in reference to Damon Runyon).

🎙️