[3]: 168  He brought back the Role Aids line, intending to recreate it with more sophisticated material for AD&D than that which TSR was producing at the time.

[3]: 169  Underground 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.

[2] In 2020, Winninger became the Executive Producer in charge of the Dungeons & Dragons studio at Wizards of the Coast replacing Mike Mearls, the previous Dungeons & Dragons design team head.

His "Dungeoncraft" column ran in Dragon from 1999-2002, during which time he also served as a contributing editor to the magazine.

He was the executive producer for Harebrained Schemes' 2014 Miniature wargaming game Golem Arcana.