Lieb was working as a clerk for the Norfolk & Western Railroad in 1909 when he began submitting biographies of players to Baseball Magazine. That led to a job with the Philadelphia News Bureau, and in 1911 he moved to New York, joined the new Base Ball Writers Association, and held honorary card No. 1. During the next 20 years he worked for the New York Sun, Evening Telegraph, and Post.
In 1931 the cigar- and pipe-smoking Lieb took a team to Japan for a profitable tour. That and other profitable investments allowed him to retire in 1934. The following year Taylor Spink induced him to write a regular column and the most important obituaries for The Sporting News, which he did from his home in St. Petersburg, Florida, for 35 years. He also did a weekly Hot Stove League column for the St. Petersburg Times. His books include the classic Baseball As I Have Known It; Connie Mack, Grand Old Man of Baseball; and team histories of the Tigers, Red Sox, Cardinals, Pirates, Orioles, and Phillies. He received the J.G. Taylor Spink Award from the Hall of Fame in 1972.