The Sinister Twelve is a team created by the Green Goblin after, while in prison, he judges that a team of villians would be needed to defeat Spider-Man. Mac Gargan was the de facto leader of the Twelve while Osborn was in prison, and it was he who kidnapped Peter Parker's Aunt May and threatened to kill her if Spider-Man did not help Osborn escape from jail. A desperate Spider-Man, with help from the Black Cat, broke Osborn out, only to be confronted with the Vulture, Sandman, Electro, Chameleon, Lizard, Hydro-Man, Shocker, Hammerhead, Boomerang, and Tombstone. Osborne officially dubbed the team the Sinister Twelve. Despite the odds, Spider-Man and the Black Cat, aided by Captain America, Iron Man, Daredevil, Yellowjacket and the Fantastic Four, managed to hold their own. Meanwhile, Osborn kidnapped Mary Jane Watson. Spider-Man pursued him, fighting off Venom along the way. Spider-Man confronted the Goblin, and finally Osborn gave a vital clue as to Aunt May's whereabouts. He was defeated by a combination of being shot by Mary Jane, struck by lightning, and attacked by Doctor Octopus, who was brainwashed by the police into trying to kill him. The Goblin fell into the river below, and Aunt May was found and saved. The rest of the Sinister Twelve were subdued by the heroes and arrested; Gargan ended up, ironically, in Osborn's old cell.