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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, and 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 Mysterious Waif 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.

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Through sheer force of personality, the Gentleman brings together the many conflicting tempers, intelligences, and agendas of the Six, bankrolling this latest collaboration with a plan he promises will bring them all wealth beyond their wildest dreams. He plays a dangerous game, a seemingly powerless old man presuming to command some of the most dangerous beings on the planet. Opposing them is Spider-Man, but rather than an obstacle, the Gentleman sees a confrontation with the webslinger as a unique opportunity, as for reasons known only to himself, he has been waiting to exact revenge on Spider-Man for Peter Parker's entire lifetime...

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.

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The short-lived The Amazing Spider-Man Series appeared to draw inspiration from the book series as it's first Myth Arc, with the inclusion of the Gentleman (played by Michael Massee) 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. The Amazing Spider-Man 2's epilogue teased the Gentleman and Harry conspiring to form the Sinister Six against Spider-Man, which would likely have been featured in both Sinister Six and The Amazing Spider-Man 3, before both were Cut Short.


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     The series as a whole 
  • Ambiguously Gay: Mysterio gets lines like "I'm not, by life preference, as conscientiously solicitous towards the ladies as Adrian", and describes the gay 1930s film director James Whale as an inspiration "both personally and professionally".
  • Ax-Crazy: Most of the Sinister Six fall under this trope, especially in the third book.
  • Badass Bystander: Mary Jane cultivates this reputation at the start of Gathering when she takes charge at Brick Johnson's funeral. This gets her an upgraded role in her next film. Over the course of Gathering and Secret, she gets further opportunities to showcase this.
  • Badass Normal: SAFE, especially Colonel Sean Morgan.
  • Bad-Guy Bar: The Machiavelli Club, though it's more of an upscale restaurant than a bar or club.
  • Been There, Shaped History: The Gentleman was aboard the Titanic when it hit the iceberg, caused the Hindenburg disaster to evade capture, and had a hand in causing the Tet Offensive.
  • Big Bad: The Gentleman, much to Doc Ock's annoyance.
  • Brainwashed: Pity underwent years of treatment and became The Gentleman's obedient servant/assassin. She does nothing without him first ordering her to.
  • Canon Immigrant: The Gentleman would later appear in the comics, making his debut in the Civil War II: Kingpin limited series.
  • Continuity Nod: The story carefully fits into Marvel Comics continuity, including a Where Are They Now bit explaining what the Six's next moves were.
  • Continuity Porn: The novels contain several references to past Spider-Man stories from the the early years all the way up to the modern era, even a reference to Spider-Man's time as a member of the New Fantastic Four alongside Wolverine, Ghost Rider and The Incredible Hulk. There's also several nods to past Spider-Man novels and short stories and even the Universal Islands of Adventure ride.
    • The Sinister Six's Day of Terror in the second book is an invoked version of this as they attack several notable locations where Spider-Man failed to save lives. Locations include a jewelry store from a little-known Untold Tales of Spider-Man issue where Spidey fails to save someone for the first time since Uncle Ben died, both Stacy murder sites, and the Empire State University football stadium from "The Longest Hundred Yards" story from Amazing Spider-Man #153.
  • Crossover: A rather odd one at the end of the third book Pity winds up picked up by Mystery Inc of all people as she's recovering from the climax.
  • Cut Lex Luthor a Check:
    • Explored with Mysterio in the first book.
    • Explored with Max Dillon AKA Electro at length. As Spider-Man points out many times, with his new powers Electro could make a killing if he worked in the energy sector. But he has so little faith, imagination, and empathy that he resigns himself to murder and terrorism.
  • Dark Action Girl: Pity plays this one straight, being able to go toe-to-toe with Spider-Man himself.
  • Demoted to Extra: Basically for Mysterio, as he goes from being the public focus threat of the first book to barely being able to stand in the third as he succumbs to the tumor that will eventually drive him to suicide.
  • Dramatic Irony: This trilogy gives one to the "Guardian Devil" storyline in Daredevil. In the latter storyline, Mysterio's reason for targeting Daredevil instead of Spidey is because he discovered recent evidence that the current Spider-Man was just a clone. This trilogy takes place just after Ben Reilly had been killed, thus rendering Mysterio's reason for not having his final scheme target his oldest enemy pointless.
  • Even Evil Has Standards:
    • The Six, with the exception of Octavius, are disgusted and horrified by the Gentleman's treatment of Pity, particularly the Vulture and Electro (to clarify, Octavius doesn't give any sign that he does approve of her treatment, but just stays silent and out of the subsequent confrontation). The Gentleman actually calls them out on this, claiming the Six have little right to complain considering some of the things they have done, but they counter that they draw a distinction between attacking strangers and going after one of their teammates.
    • 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.
    • The Gentleman justifies his decision to leave his enemies' children alone as this, although in his case 'standards' more refers to things he won't do because he considers it beneath him rather than out of any moral consideration. As Fiers states himself, he only avoids killing children so that he can have a more sporting time of it by facing opponents who understand why he's doing this and might even try to resist him, rather than him not wanting to cross a line.
  • Evil Cannot Comprehend Good: The Gentleman all over, utterly incapable of understanding why Peter would act as Spider-Man rather than find a more profitable way to use his powers.
  • Evil Gloating: Doctor Octupus tells the Gentleman that he would be happy to explain in great detail how he had worked out his plans to betray them and proceeds to to just that.
  • Evil Laugh: Mysterio is fond of these to the point that by the second book, Spidey suspects them being played from a tape.
  • Evil Old Folks: The Gentleman, who is orchestrating the whole evil plan, is said to be well into his 90s (the Vulture, who is of a similar generation, muses that this is basically the only thing he likes about the Gentleman).
  • Faux Affably Evil: The Gentleman.
  • For the Evulz: While the Gentleman considers himself a businessman seeking profit above all else, he is shown to be very sadistic when dealing with his enemies; one scene reveals that he earned the enmity of his long-time foe Doctor George Williams when he not only set up a bomb to kill Williams' wife on their wedding night, but even arranged for a congratulatory telegram to be delivered just after the bomb went off.
  • Four Lines, All Waiting:
    • The narration switches between Spider-Man's traditional narrative, the Gentleman's as he lays plans, members of the Six as they go about their business, and Mary Jane having her sub-plot.
    • Several sections are also from the POV of civilian characters, such as Arnold Sibert, the film critic at the Daily Bugle.
  • Good Scars, Evil Scars: Pity has scars running down her cheeks, but the Gentleman did this intentionally to make her look more helpless and nonthreatening.
  • Incurable Cough of Death: Mysterio has one of these, since it's set just before "Guardian Devil" in Daredevil.
  • Kick the Dog: Any time discussion of the Gentleman's past comes up it's just an excuse for him to do this with a smile.
  • Large Ham: DON'T PRESUME TO FORGET OCTAVIUS, YOU FOOL!
  • Lightning Bruiser: Electro naturally, but surprisingly Mysterio as well, having extensive training as a martial arts stuntman.
  • 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.
  • Out-Gambitted: The Gentleman, then the Chameleon, then Doc Ock all have their master plans fail when the next person comes along.
  • "The Reason You Suck" Speech:
    • In the Distant Prologue to the third book, the Gentlemen gives one to the Alfred Malik Red Skull, criticizing him for trying to capitalize off of the infamy given to the identity by Johann Schmitt (an old associate of Fiers) and correctly predicting that even if he manages to avoid being caught by the international authorities he's baiting by posing as a Nazi war criminal, he'll just meet his end at the hands of the true Skull for his impersonation once Schmitt re-emerges from the shadows.
  • Remember When You Blew Up a Sun?: 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 Boss Rush against him, he sent them all running by mid-afternoon to get the guy to back down. Doubles as a recap. This example is Played for Laughs, 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.
  • Red Shirts: The SAFE troops.
  • Running Gag: A minor villain 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 aside from his ruthlessness.
  • Sharp-Dressed Man: The Gentleman is always in an impeccable tailor-made suit.
  • Shout-Out / Lawyer-Friendly Cameo: Many. Castro is fond of these.
  • Siblings in Crime: Gustav Fiers, aka The Gentleman, and his anarchist Professional Killer brother, Karl Fiers, aka The Finisher. For those unaware, Karl Fiers was the man who killed Richard and Mary Parker for Red Skull II.
  • Sinister Silhouettes: The Machiavelli Club is designed so that everyone sits in the shadows and can't be overheard by others nearby.
  • Smug Snake: The Gentleman, who is not nearly as intelligent as he thinks he is, as he underestimates the Chameleon and Doctor Octopus.
  • 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.
  • Two-Part Trilogy: Despite the fact that it's made clear from the beginning that the novels are a trilogy, Gathering is largely standalone compared to the following two books. The Sinister Six is merely a subplot with Mysterio being the main antagonist of the book, while the two sequels are more directly related as the Six come together and the Gentleman explains his plans.
  • Villain Ball: The Gentleman quite possibly would've gotten away to enact the last part of his plan to release the catalyst over New York City had he not insisted on betraying the Six and being a dick to the Chameleon.
  • Villainous Crush:
    • Electro AKA Max Dillon develops one on Pity throughout the trilogy. It humanizes him, but also points out his hypocrisy.
  • You're Insane!: Conversed and defied in Revenge over The Gentleman's treatment of Pity:
    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.

     Gathering of the Sinister Six: 
  • Call to Adventure: Spider-Man initially doesn't want to get involved with the suicide of Brick Johnson. Until Mysterio crashes the funeral, endangers everyone present and announces that he will be going after the film industry.
  • Cut Lex Luthor a Check: The first novel in particular discusses the irony of Mysterio's situation. The main thing that pushed him over the edge and caused him to become a supervillain was that he was an underpaid B-movie makeup and effects artist who felt nobody appreciated him or took his work seriously. Now, in the age of modern sci-fi and superhero blockbusters, someone with Mysterio's skills could make millions by working on major Hollywood productions, but his criminal actions have damaged his reputation to such a degree that he has zero chance of landing a legitimate job ever again.
  • Disproportionate Retribution: When Quentin Beck and Brick Johnson were both young in Hollywood trying to make names for themselves, Brick refused to help Quentin get a job. Later after becoming Mysterio, he spends a year driving Brick insane with hallucinations, ruining his career and sending him into a state of suicidal depression and seeming insanity. Then he crashes the funeral and tries to kill everyone present.
  • Establishing Character Moment: After making a crazy request of room service and disparaging New York's fine arts, architecture, and people, the Gentleman orders his assistant Pity to do nothing but lie on the suite floor in total darkness while he's out all day, to kill anyone who might accidentally enter, and that she'll only be allowed to eat or drink when he comes back if she does so.
  • Underestimating Badassery:
    • 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.
  • Unsatisfiable Customer: In the first chapter, the Gentleman asks room service to replace his pad phone with a rotary phone by the time he gets home that night. He doesn't really care about the phone, but says that making an unreasonable request at an exclusive establishment right off the bat ensures they'll be falling over themselves to serve you for the rest of your stay.
  • Villains Out Shopping:
    • When Chameleon shows up to recruit the Vulture he has just returned from buying groceries.

     Revenge of the Sinister Six 
  • After Action Patch Up:
    • After the Day of Terror is over, Spider-Man gets some first-aid, a long bath, and some well-deserved sleep.
    • He also has an involuntary one halfway through, when he faints after fighting Doctor Octopus.
  • Becoming the Mask: Mary Jane tells Peter that he's spending so much time as Spider-Man that he's treating it as his main life and Peter Parker as his alter ego after a series of failed attempts to get the intelligence profiles of his parents. Mary Jane points out that while it would risk the secret identity of Spider-Man to ask about the Parkers, Peter has a better chance of getting the files and it doesn't risk him being exposed.
  • Boring, but Practical:
    • Every other villain resorts to spectacular displays of superpowers to keep their hostages in place during the Day of Terror. Chameleon simply holds an AK-47 on them.
  • Combat Parkour:
    • Discussed during Spider-Man's fight with Doc Ock. He gets beat up fighting him in close quarters, and moves the fight outside where he has more room.
  • Face Death with Dignity: How Mary Jane handles The Chameleon when he traps her and a group she's with during the Day Of Terror. Instead of having everyone Zerg Rush the villain from across a football field where he'll have plenty of time to gun everyone down, she calmly walks down the field to force him to confront the reality of what he's doing. It makes him hesitate long enough so when he gets distracted when others make a run for it, she's close enough to take him down, saving everyone.
  • Exposition Dump:
    • The epilogue is one, as Colonel Sean Morgan and Dr. George Williams explain just who the Gentleman is.
  • Heroic BSoD: Spider-Man 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.
  • Heroic R Ro D:
    • Spider-Man starts reaching this as the climax nears. He gets slammed against half the buildings in Midtown, gets a concussion and "one of the worst beatings he'd had in months" from Doc Ock, gets his leg cut open, his side burned, a bunch of painful strikes from Pity, and is nearing the edge of total exhaustion by story's end. And he gets a cramp.
  • History Repeats: During the Sinister Six's Day of Terror, Doc Ock returns to the site where he killed Captain George Stacy and during the ensuing fight with Spider-Man, a piece of concrete once again dislodges and falls from the rooftop towards a small child as the officer in charge of the scene once again pushes the child out of harm's way. This time, however the officer manages to survive as well.
  • Kansas City Shuffle:
    • Electro turns out to actually be Mysterio during the Day of Terror.
    • It's revealed that the entire Day of Terror was one of these, designed to draw people and authorities' attention while Electro and Pity stole the Catalyst from lockup.
  • Kick the Dog:
    • The Gentleman does this to demonstrate his hold over Pity at the end of his first meeting with the Six, ordering her to crush a canary she was admiring.
  • Loving a Shadow: Facing a holographic recreation of Gwen Stacy's death, Spider-Man muses that things with Gwen wouldn't have worked out even if she had survived, as Gwen wanted peace where Peter can now admit at least to himself that he seeks crusades, even if he still cares for her.
  • Mission Briefing:
    • Spider-Man gets this at the start, as Morgan explains to him how the Six have escaped custody and are mobilizing as a team again.
  • No-Sell:
  • Tap on the Head:
    • Played realistically. Spider-Man faints, but wakes up a few minutes later, and it's revealed that he fainted because of a concussion Doc Ock inflicted during their fight.
  • "The Reason You Suck" Speech:
    • Mary Jane calls the Chameleon out on his choice of location for the Day of Terror, claiming that he picked a relatively obscure example of Spider-Man's failures and only acted when Spider-Man was publicly occupied elsewhere because he knows he'd never stand a chance if he was forced to face the wall-crawler directly.
  • Run the Gauntlet: The Six declare a planned "Day of Terror", where they will individually return to places where Spider-Man failed to save lives and endanger lives once more. After a multitude of challenges, they then return to the Daily Bugle offices where they made the declaration and insist Spider-Man come in and fight them all once.
  • Unstoppable Rage:
    • Spider-Man enters one of these when Doc Ock pisses him off enough during their fight. He stops wisecracking and devotes 110% of his energy to beating him.
  • Villain Ball: During the final fight, Spider-Man notes that Electro is powerful enough to kill him easy, but he enjoys playing with his food too much, meaning Spider-Man has to run away a lot, but also gets the time he needs to think up a counter-attack.
  • "Well Done, Son!" Guy:
    • SAFE therapist Troy Saberstein posits that Jameson's antagonism serves as a version of this for Spider-Man. Spider-Man knows it's not quite right, but finds it closer to true than he's comfortable with.

     Secret of the Sinister Six 
  • Apocalypse How:
    • The Gentleman's plan turns out to be a Class 1. By detonating a memory-wiping EMP and an ink-destroying airborne Catalyst over New York, all paper and electronic records (including money marking) will be destroyed. Since New York is a world financial capital, this will have devastating effects on American currency and the world economy, and definitively turn New York into hell on earth.
  • Betrayal Insurance: It turns out that the Gentleman has been keeping some in store for Doc Ock. It comes in the form of an internal charge in his robot arms that the Gentleman can activate at any time.
  • Big Damn Heroes: SAFE arrives just in time to rescue Spider-Man and Pity from frigid North Atlantic waters after their plane crashes.
  • Book Burning:
  • Boring, but Practical:
    • The Gentleman has an elaborate plan in place to ruin Spider-Man's city. But when it comes to ruining his personal life, he simply has Pity plant a bomb in the Parker household so he can kill Mary Jane at any time.
    • SAFE also puts up a good fight against Electro and Vulture, despite only having guns, their hoverships, and teamwork on their side.
  • EMP:
    • The Gentleman's final plan involves the Six stealing a generator capable of generating a massive one.
  • Enemy Mine:
    • Spider-Man successfully lures Pity to his side by pointing out that the Gentleman is in danger.
  • Evil Is Petty:
    • As the Gentleman lays dying, all he can think about is that he's going to die penniless, having converted all his wealth to the hoard of treasures Octavius just stole, and having been relieved of his ring and wallet by Chameleon. The idea of dying penniless brings him to tears.
  • Failed a Spot Check: It takes until the final battle for Spider-Man to realise that in all the concern about finding Doctor Octopus, he and SAFE haven't registered the absence of the Chameleon, who has already shot the Gentleman to take his place.
  • Faking the Dead: Spider-Man pulls off a truly epic version of this when Electro blasts him into a buffet. It involves lasagna.
  • 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, dying penniless and humiliated. To rub salt in the wound, with no friends or family to claim his body, Fiers is dumped in an unmarked grave in Pauper's Field, alone and forgotten, while his old rival Williams lives another six months and has a funeral attended by thousands.
  • Kick the Son of a Bitch:
    • 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.
  • Gambit Pileup: At the climax, the Gentleman is escaping aboard his plane ready to betray everyone, except Doc Ock already worked everything out and is going to steal his plane and go ahead with his plan. Except it's not the Gentleman, it's the Chameleon who already betrayed the Gentleman and is going to do the exact same thing. Then Spidey and Pity show up because Spider-Man turned her to his side so he could catch the Gentleman.
  • Loving a Shadow:
    • Dillon's crush on Pity is ultimately dismissed as this. He pities her, but has no idea how to actually befriend her.
  • Mook Horror Show:
    • We get an example from the good guys' point of view when the Six attack a facility to steal a power generator. Doc Ock, Electro, and Vulture all sadistically killing personnel with glee.
  • Moral Myopia: When the Gentleman strikes Pity, the Six - particularly Vulture and Electro - come to her rescue. The Gentleman points out the hypocrisy of this, as both Vulture and Electro killed women her age only the day before.
  • Nice Job Fixing It, Villain: Essentially invoked when Doctor George Williams- the Gentleman's longest-living adversary- observes that the scale of his foe's plan is his final mistake, as he's raised the stakes so high the world can't afford to let him get away this time.
  • No-Sell: One of the ways Spider-Man gets through to Pity is by refusing to heed her poor-little-me aura:
    Spider-Man: Listen to me, dammit.
  • Oh, Crap!: The Chameleon, after when Doc Ock comes on board his escape plane.
  • The Reveal: Several.
    • The Gentleman is using the generator to an EMP, and has already stolen a Catalyst that will destroy all paper records.
    • The Gentleman has two bombs that can kill Doc Ock and Mary Jane at any time.
    • The Gentleman is going to betray the Six and run away.
    • Doc Ock saw this all coming, and is betraying the Gentleman first.
    • And last of all, the Chameleon beat Ock to it and murdered him several minutes ago.
  • Underestimating Badassery: The Gentleman is finally defeated because he underestimates the Chameleon and Doctor Octopus, believing that he could always see through the Chameleon's disguises and that he had the perfect means to control Octavius, only to be shot by the Chameleon just before Doc Ock reveals that he had already deduced how the Gentleman intended to betray them.
  • Villains Out Shopping:
    • Electro is introduced in this book buying Pity a bouquet of flowers.
    • Another chapter has the Gentleman shopping for the most expensive luxury jewelry, which reveals a substantial part of his scheme.
  • Worthless Currency: Part of the Gentleman's plan. By devastating the world economy, he'll reduce the American dollar's value substantially, while the value of art, jewelry, and historical items - all things the Gentleman has in abundance - will go UP substantially .

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