In terms of a Machiavellian scheme, the TV trope referred to as the Xanatos Gambit is a good one. Named for David Xanatos, a character from the 90's Disney cartoon Gargoyles, a Xanatos Gambit is one wherein a plan is enacted where all possible outcomes benefit the person who starts the scheme.
Say, for instance, you start a fight to steal an object. You lose the fight to the object's guardian. But the fight was posted on YouTube and gained you massive popularity for "defending" yourself against a clearly superior opponent. Your newfound popularity allows you to get invited to a party where the object is, which you can now steal. The whole thing is - you knew that if you lost to the object's guardian, you could spin this in your favor to get close to the object. In other words, that was part of the plan from the beginning. That's a Xanatos Gambit.
Write a story in which the villain repeatedly uses the Xanatos Gambit - enacting schemes wherein all possible outcomes result in a victory for the villain.
There's a reason why Gargoyles was so popular - it was damn smart. The cartoon also took Shakespearean characters (Macbeth and Puck were major characters) and mythology (Avalon played a major role) to create a well-constructed plotline and smart world building. Even ten years later, it still stands up as being almost too smart for a kid's show.