edit In the Mass Effect fanfic The Council Era, the advisor to the Krogan Overlord, Halak Marr, definitely qualifies as a Chessmaster. Both Starcraft and Brood Wars actually have several of them. In Season 4 of The Legend of Korra, averting this trope is part of the reason why Kuvira usurps the United Republic-backed Prince Wu and crowns herself Emperor of the above-mentioned Earth Kingdom (which she renames "Earth Empire.
In Vampire: The Masquerade, the elders are like this. If everyone just accepted that she is always playing them no matter how vulnerable or uncertain she seems, central Theme of A Clockwork Orange then it probably wouldn't change the actual outcome, but they wouldn't waste time and energy trying to beat her at her own game. As an example, she encounters her half-brother Roland Niedemann, who has repeatedly tried to kill her. When the Golden Horde rolls in from the east, you'll find stack after stack of elite horse archers and heavy cavalry led by Dreaded Four Star Badasses. Is it his power all along?