Ray Winninger was a competitive chess player as a child, and at age nine he discovered Avalon Hill games, and Dungeons & Dragons while looking for chess opponents at a local hobby shop/game store. He designed his first game as "a futuristic man-to-man miniatures system", and by the age of fourteen he had designed an enormous campaign world for the Dungeons & Dragons game system. His first published work was an adventure called Countdown! for FASA's Doctor Who role-playing game. He worked for TSR, including work on Dungeons & Dragons, throughout the 1980s and early 1990s. Winninger was the co-designer of DC Heroes and Torg. Winninger then worked at Mayfair Games, and became Mayfair's Editorial Director following the release of Chill.:168 Winninger resurrected the Role Aids line, determined to recreate it with AD&D material that was more sophisticated than what TSR was offering at the time.:168 Winninger designed the Underground (1993) role-playing game for Mayfair Games.:169Underground was set in the year 2021 and "allowed players to assume the roles of superhuman, genetically enhanced soldiers fighting a patriotic war to take their society back from a corrupt government"; when Mayfair Games withdrew much of its support of the game despite its popularity, Winninger moved onto other projects. Mayfair was also to produce a game called D.O.A. by Greg Gorden with major contributions by Winninger, but the game was never published.:170 He worked for Dragon magazine, first taking over the "RPG reviews" column from Chris Pramas, before moving on to "Dungeoncraft", a column for guiding Dungeon Masters to create their own campaign worlds. He also worked as a contributing editor of Dragon magazine. Winninger later became a senior platform strategist at Microsoft.