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It was created by Herbert F. Simons, a sportswriter for the Chicago Daily Times, in 1942. Simons first published the magazine in August 1942, and served as its editor-in-chief until 1963. In 1981, Joan Whaley was published as its first female contributor.
After publishing on a 9 or 12 issues per-year schedule, in 2009 it scaled back to six with National and American League schedules, directories, pre-season rosters, Major League Baseball history, and one-on-one player interviews, such as in the "Game I'll Never Forget" feature.
In March 2012, Baseball Digest merged with professional scouting service ProScouts LLC. The relaunch included major changes to the magazine's format including being published in full-color for the first time, an increase in editorial content such as scouting reports by veteran MLB scouts, and more newsstand availability.
Other current features include batting, pitching and fielding statistics, a "fans speak out" letters section, player profiles, trivia questions in a Quick Quiz, previews, rules review, a crossword puzzle, and analysis of upcoming prospects. In addition, Baseball Digest has provided season-ending awards for decades: Baseball Digest Player of the Year, Pitcher of the Year, and Rookie of the Year, plus annually presents its All-Star rookie team award.
In May 2018, Rick Cerrone, former Public Relations Director with the New York Yankees (and not to be confused with the Yankees catcher of a similar name), became the fourth editor in the iconic magazine's history. Cerrone was tasked with 're-imagining the publication from the ground up beginning with the September/October issue of 2018.  Starting with the January/February 2019 issue, the publication upgraded to a heavier paper stock and increased the number of pages published.
Grandstand Publishing, LLC, announced July 4, 2019, the introduction of BaseballDigestArchive.com, a web-based subscription service that provides users the opportunity to read, search and explore every issue of Baseball Digest ever published -- more than 800 issues, 64,000 pages, and 77,000 features in total. It includes past articles published by the magazine, with statistics and articles related to specific teams or players, as well as past scouting reports.
In May 2021, ProScouts LLC, headed by entrepreneur David Fagley, purchased the remaining outstanding shares held by long-time Publisher Norman Jacobs, who remains on as Publisher Emeritus.