Spider-Man has been caught in plenty of bad situations before, but one of his most dire was definitely his battle with the Sinister Twelve, a major evolution of the traditional Sinister Six. This new team was led by none other than Norman Osborn, the Green Goblin himself. Assembling such a large team was a plan Norman had long had in the works, ever since he learned Spider-Man’s secret identity. As a result, the danger and stakes involved had never been higher, as the Green Goblin also had Peter Parker’s Aunt May held hostage as well.

This major showdown was part of an arc from writer Mark Millar with artists Terry and Rachel Dodson entitled “The Last Stand” from the Marvel Knights: Spider-Man series published between 2004-2006. Marvel Knights was a more serious, grounded, and more adult take on the Webslinger, seeing Spider-Man grappling with a lot of major threats all at the same time, the primary ones being his secret identity becoming compromised, as well as the abduction of his Aunt May. Not only that, but several of his foes had been attacking him in quick succession without ceasing. Finally, Peter is called to have lunch with the Scorpion, who reveals Norman as the mastermind behind Aunt May’s kidnapping. In order to see her again, all Spider-Man has to do his help the Green Goblin break out of prison. Reluctantly, Spider-Man believes he has no choice, agreeing to the terms and having Black Cat lend a hand with her expertise to help free Norman.

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However, breaking Norman out of his cell was of course a trap. As soon as Spider-Man and Black Cat get him out of Riker’s, Spider-Man is bombarded by several of his foes, all of whom have been hired by the Green Goblin. He also designed new upgrades for all of them to be as effective and deadly as possible for this exact night and purpose, assembling together as the Sinister Twelve, forcing Spider-Man to make a last stand while the Goblin left to go kill Mary Jane (who was Peter’s wife at the time).

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However, there were even more surprises like Scorpion arriving without his armor, instead of wearing Eddie Brock’s symbiote suit, becoming the new Venom. The Sinister Twelve take turns relentlessly beating Spider-Man into a pulp, and the Webslinger sees absolutely no way to defeat them all and save his family, believing that his failure and death was near. However, a good surprise occurs with the arrival of an assortment of heroes including the Avengers, Fantastic Four, and Daredevil, all of whom were summoned by SHIELD thanks to a phone call from Mary Jane. This provided Spider-Man with the opportunity to go after Green Goblin, who had already grabbed Peter’s wife, holding her over the same bridge where he killed Gwen Stacy, Peter’s first love. After Spider-Man saved Mary Jane (with two web lines) and defeated the Goblin, he also figured out where Norman had been hiding Aunt May: in his Uncle Ben’s grave. Thankfully, Peter was able to get there in time and save his Aunt before she ran out of air.

Naturally, this story changed a lot of things for Spider-Man, due to the fact that he was so close to losing everything and the two people he cared for the most. Green Goblin took Spider-Man to the very brink with his Sinister Twelve, and the outcome of this battle laid that groundwork for Peter to finally join and trust the Avengers, seeing the benefits of having a whole team of superheroes backing him up. Soon after, Iron Man would actually let Peter and his family move into Stark Tower, giving them some much-needed safety and security. It would also lead into Mark Millar’s Civil War, where Spider-Man was convinced to reveal his secret identity to the world in favor of the pro-registration movement. Seeing as how it had already been compromised so much already as seen in “The Last Stand”, it probably helped his decision to a good degree.

All in all, Spider-Man’s battle with the Sinister Twelve ended up becoming one of his most deadly fights, as he literally almost died from the showdown. However, it was also one of his most defining, not because he defeated them, but because Spider-Man ultimately didn’t have to thanks to the rest of the Marvel heroes he learned to trust and rely on more. That being said, here’s hoping that there never becomes a Sinister 24.

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