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The Sinister Six Trilogy is a series of books written by Adam Troy Castro about Spider-Man facing off against a new Sinister Six, consisting of Doctor Octopus, The Chameleon, The Vulture, Mysterio, Electro and Pity, and behind them a mysterious benefactor known as The Gentleman.

The first book, titled The Gathering of the Sinister Six is about Mysterio taking revenge against old enemies in the film industry while the Gentleman gathers the rest of the Six. Book two, Revenge of the Sinister Six, is about the Six's Day of Terror in which they try to defeat Spider-Man first one by one, then all at once. Book three, Secret of the Sinister Six, covers the Gentleman's real plan and everyone finding out about it.

The series shows examples of:

  • Ax Crazy: Most of the Sinister Six fall under this trope, especially in the third book.
  • Badass Normal: Most of SAFE in general.
  • Big Bad: The Gentleman, much to Doc Ock's annoyance.
  • Big Damn Heroes: SAFE arrives just in time to rescue Spiderman and Pity from frigid North Atlantic waters after their plane crashes.
  • Brainwashed: Pity underwent years of treatment and became The Gentleman's obedient servant/assassin. She does nothing without him first ordering her to.
  • Call to Adventure: Spiderman initially doesn't want to get involved with the murder/suicide of Brick Johnson. Until Mysterio crashes the funeral, endangers everyone present and announces that he will be going after certain targets in the film industry.
  • Dark Action Girl: Pity plays this one straight, being able to go toe-to-toe with Spiderman himself.
  • Determinator: Pity, against her will.
  • Faux Affably Evil: The Gentleman appears to be Affably Evil. In reality he's a Complete Monster.
  • Heroic BSOD: Spiderman undergoes one when he gets up to the news room in the Daily Bugle and finds the butchered remains of all his friends. Luckily it was just one of Mysterio's tricks.
  • Karmic Death: The Gentleman who always put wealth above anything else, is killed by The Chameleon and has all of his fortune stolen from him. To rub salt in the wound, a detective whose life The Gentleman ruined confronts him as he lays dying. He thinks he has the final laugh until the detective points out he'll die a pauper. The detective then lays a penny on the opposite end of the room and leaves knowing The Gentleman will crawl for it.
  • Kick the Dog: Anytime discussion of the Gentleman's past comes up it's just an excuse for him to do this with a smile.
  • Large Ham: Dr. OCTAVIUS, YOU FOOL! would qualify.
  • Luke I Am Your Brother: The final book hints that Pity might be Peter's long lost sister. She isn't
  • Ninja Pirate Zombie Robot: Mysterio's robotic sharks.
  • Oh Crap: The Chameleon, after betraying the Gentleman and taking his fortune when Doc Ock comes on board his escape plane.
  • Red Shirts: The SAFE troops.
  • Running Gag: A minor villian named the Candy Man shows up throughout the series. Every time he's subdued in less than a minute.
  • Screw the Rules, I Have Money: This is about the only reason the Gentleman is a real threat.
  • Shout-Out:
  • Siblings in Crime: Gustav Fiers, aka The Gentleman, and his anarchist Professional Killer brother, Karl, aka The Finisher.
  • Smug Snake: The Gentleman who is not nearly as intelligent as he thinks he is.
  • The Sociopath: The Gentleman, his brother Karl, and all the members of the Sinister Six, most notably Dr. Octopus.
  • Tailor-Made Prison: In the beginning Electro is locked up in a plastic box suspended in water.
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