The term "Grandmaster" was appropriated by Dr. Eggman after the remnants of the original Dark Legion joined the Eggman Empire under Lien-Da; the term was subsequently applied to all of the various Sub-Bosses. (StH: #184, #214)
List of All Grandmasters
In order of succession:
- Menniker - founded the Dark Legion, killed by exploding missile alongside Aaron when the latter detonated it.
- Moritori Rex - Replaced Tobor and infiltrated the Brotherhood of Guardians; poisoned Janelle-Li, maintained Legion bases in the Prime Zone
- Luger - Led an invasion that was thwarted by Thunderhawk. Was also the first Grandmaster to willingly order the Dark Legion's return to the Twilight Zone after escaping a second time. He was later atomized by Lien-Da.
- Kragok - Led several battles against Knuckles and the Chaotix. Was killed by Tobor after colliding into the Battle Cruiser.
- Dimitri - Took over the Legion first as Enerjak, later ruling as himself until he was betrayed by Lien-Da.
- Remington - Caused a civil war when trying to become Grandmaster, becoming leader of the former Frost Legion faction until his memory was restored by the second Enerjak.
- Lien-Da - Led the Dark Legion resistance on Angel Island, later became Grandmaster of the former Flame Legion faction. She subsequently became the Grandmaster of the echidna branch of the Dark Egg Legion after disposing of Dimitri.
Dark Egg Legion
- See: Sub-Boss
- Lien-Da - Grandmaster of the Albion Dark Egg Legion-currently trapped in another zone.
- Duck "Bill" Platypus - Grandmaster of the Downunda Dark Egg Legion-double agent for the Downunda Freedom Fighters.
- Drago Wolf and Razorklaw - Joint Grandmasters leading the Soumerca Dark Egg Legion, which includes members of the Wolf Pack Nation and the Mysterious Cat Country.
- Akhlut - Grandmaster of the Northern Tundra Dark Egg Legion.
- Beauregard Rabbot - Grandmaster of the Great Desert Dark Egg Legion.
- Bride of Conquering Storm - Grandmaster/Bride of the Dragon Kingdom Dark Egg Legion/Raiju Clan.
- Mordred Hood - Grandmaster of the Mercia Dark Egg Legion.
- Diesel - Grandmaster of the Efrika Dark Egg Legion.
- The Foreman- Grandmaster of the Nerb Dark Egg Legion.
- Iron Queen - Grandmaster of the Eurish Dark Egg Legion.
- Hugo Brass - Grandmaster of the Eurish Dark Egg Legion. Replaced by the Iron Queen.
- Dimitri - Grandmaster of the New Megaopolis Dark Egg Legion. Replaced by Lien-Da.