History Literature / SpiderManSinisterSixTrilogy

* KickTheSonOfABitch:
** [[spoiler: As the Gentleman lays dying of a gunshot wound, his old rival George Williams appears, and instead of helping him, places a single penny he knows the Gentleman will crawl for at the other end of the freezing air hangar.]] It's cruel and petty, but he's definitely earned it.

''The [[Franchise/SpiderMan Sinister Six]] Trilogy'' is a series of books written by Adam Troy Castro about Franchise/SpiderMan facing off against a new Sinister Six, consisting of ComicBook/DoctorOctopus, [[ShapeShifter The Chameleon]], [[EvilOldFolks The Vulture]], [[MasterOfIllusion Mysterio]], and [[PsychoElectro Electro]]. They are brought together by the Gentleman, a man well over eighty years old who has caused, participated in, and most importantly profited from many of the most heinous criminal acts of the twentieth century. He is a mundane human with no superpowers but enormous wealth, charisma, and criminal skill. He brings with him the new sixth member of the Sinister Six, a MysteriousWaif known as Pity, a mute young woman with power over shadows who fears the Gentleman above all things yet will obey his orders without question; the juxtaposition causes those who see the conflict within her to feel the emotion that is her name.

The first book, titled ''The Gathering of the Sinister Six'' is about Mysterio [[DisproportionateRetribution taking revenge against old enemies in the film industry]] while the Gentleman [[ExactlyWhatItSaysOnTheTin 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 Franchise/SpiderMan first one by one, [[BossRush then all at once]]. Book three, ''Secret of the Sinister Six'', covers the Gentleman's real plan and [[GambitPileup everyone finding out about it]].

'''The [[Franchise/SpiderMan Sinister Six]] Trilogy''' is a series of books written by Adam Troy Castro about Franchise/SpiderMan facing off against a new Sinister Six, consisting of ComicBook/DoctorOctopus, [[ShapeShifter The Chameleon]], [[EvilOldFolks The Vulture]], [[MasterOfIllusion Mysterio]], and [[PsychoElectro Electro]]. They are brought together by the Gentleman, a man well over eighty years old who has caused, participated in, and most importantly profited from many of the most heinous criminal acts of the twentieth century. He is a mundane human with no superpowers but enormous wealth, charisma, and criminal skill. He brings with him the new sixth member of the Sinister Six, a MysteriousWaif known as Pity, a mute young woman with power over shadows who fears the Gentleman above all things yet will obey his orders without question; the juxtaposition causes those who see the conflict within her to feel the emotion that is her name.

* ExpositionDump:
** The epilogue is one, as Colonel Sean Morgan and Dr. George Williams explain just who the Gentleman is.

** The Gentleman's harsh treatment of the Six as a whole was also referenced to a lesser degree earlier on when he brought up the fact that the Chameleon was defeated by a civilian (specifically, Mary Jane) during the Day of Terror a week ago just to rile the Six up, when the rest of the team (even Octavius) had been avoiding that same topic out of respect for their colleague's feelings.

* NinjaPirateZombieRobot: Mysterio's robotic sharks.
* OutGambitted: The Gentleman, then the Chameleon, then Doc Ock all have their master plans fail when the next person comes along.

* RememberWhenYouBlewUpASun: Early in book 3, a minor villain named the Disk Jockey gets into a fight with Spider-Man. He takes a hostage and Spider-Man tells him about the six people trying to kill him, some of the most deadly people alive. He mentions that he's fought all of them and in their most recent BossRush against him, he sent them all running by mid-afternoon to get the guy to back down. Doubles as [[AsYouKnow a recap]]. This example is PlayedForLaughs, as the Disk Jockey is portrayed as a singularly uninformed man (not unintelligent, but very much in a bubble) who has missed the many terrorist attacks, supervillain invasions, alien incursions, and other calamities that have hit New York in the past several years. Working in an appliance repair shop, he decides to use his gadgeteering knowhow to build a suit full of gimmicked gadgets, establish a villainous identity, and then use them to steal and commit crimes, all the while honestly thinking he is the very first person to ever try this. He doesn't know or recognize Spider-Man when he sees him, and has no concept of what a costumed hero even is. He is so ludicrously unaware that Spider-Man takes pity on him and gives him the aforementioned review of recent events, and after this quick dose of perspective, he surrenders quietly.

* VillainBall: The Gentleman quite possibly would've gotten away to enact the last part of his plan [[spoiler:to release the catalyst over New York City]] had he not insisted on [[spoiler:betraying the Six and being a dick to the Chameleon]].

* UnderestimatingBadassery:
** Pity constantly emanates a helpless, I-don't-like-this-at-all aura no matter what she's doing, whether it be obeying the Gentleman or fighting you to the death. But this means even hardened super-villains don't see her as a threat, making putting one over them even easier.

* FakingTheDead: Spider-Man pulls off a truly epic version of this when Electro blasts him into a buffet. [[NoodleImplements It involves lasagna.]]

* OhCrap: The Chameleon, after when [[spoiler: Doc Ock]] comes on board his escape plane.

The short-lived ''Film/TheAmazingSpiderManSeries'' appeared to draw inspiration from the book series as it's first MythArc, with the inclusion of the Gentleman (played by Creator/MichaelMassee) as a mysterious shadowy figure who meets with both Dr. Curt Connors and Harry Osborn at the end of both movies, revealing a connection to both Norman Osborn and Richard Parker, Peter's father. ''Film/TheAmazingSpiderMan2'''s epilogue teased the Gentleman and Harry conspiring to form the Sinister Six against Spider-Man, which would likely have been featured in both ''Film/SinisterSix'' and ''The Amazing Spider-Man 3'', before both were CutShort.

[[folder: The series as a whole]]

* {{Crossover}}: A rather odd one at the end of the third book [[spoiler: Pity winds up picked up by [[WesternAnimation/ScoobyDoo Mystery Inc]] of all people as she's recovering from the climax.]]

** Franchise/CarmenSandiego is part of the Machiavelli Club, along with [[Franchise/{{Batman}} Jack Napier]], Hannibal Lecter and [[Film/{{Unbreakable}} Mr. Glass]]. Among others. Moriarty was a founding member, and [[Franchise/DieHard the Gruber Brothers]] and a villain from an Ellery Queen novel have been members. The Gentleman briefly converses with two brothers, [[Film/TradingPlaces Randolph and Mortimer]], who made their money on the futures exchange, and wonders how they earned a place at the club as they are no more 'evil' than standard stockbrokers.

** The cast from Franchise/ScoobyDoo shows up at the end of the final book.

-->'''Spider-Man:''' You're insane!
-->'''The Gentleman:''' Not at all. Simply evil. Those of you who happen to be players on the other side have so much trouble understanding the difference.

[[folder: Gathering of the Sinister Six:]]

[[folder: Revenge of the Sinister Six]]

[[folder: Secret of the Sinister Six]]