The Chessmaster gets their name from their ability to manipulate events (that is, they cause events to develop in the way they want in order to produce a desired result through planning them out) as if they were pieces on a chessboard. Chessmasters tug at their strings of influence, patiently move their pieces into places that often seem harmless or pointless until the trap is closed, and get innocent Unwitting Pawns (who else?) to do all the heavy lifting. The best will also have layers upon layers of misdirection and backup plans in case some unexpected hero appears to gum up the works.
Fan Casting
Professor Moriarty
Emperor Palpatine
Scar (Lion King)
Grand Admiral Thrawn
Claude Frollo
Petyr "Littlefinger" Baelish
Kingpin
Ernst Stavro Blofeld
Stan Edgar
V (V for Vendetta)
Lex Luthor
Tywin Lannister
Ra's al Ghul
Doctor Doom
Hades
Randall Flagg
Darth Maul
Rumplestiltskin
Red Skull
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