One of Spider-Man's greatest enemies Norman Osborn, aka the Green Goblin, is a bit of an evil mastermind. He's hurt Spider-Man worse than any other villain by far. This is mostly due to the supervillains murder of Spidey's first serious girlfriend, Gwen Stacy and the terrible parent that he was to his best friend Harry Osborn.
Peter Parker and Norman Osborn have had many battles over the years. Norman continues to scheme and develop many masterplans with the goal of completely destroying Peter's life. Here are five of Norman Osborn's smartest plans and five that were destined to fail.
10 Failure - Sinister Twelve
After escaping prison using blackmail and other seedy methods, Norman assembled a team that was finally capable of defeating Spider-Man. Dubbed the Sinister Twelve, this was a larger team of villains than Spidey had ever faced before.
This plan might have had a chance of working but there was one big problem. Norman didn't account for the fact that Spider-Man might get reinforcements. After a team of Avengers arrived to aid the webhead, the Sinister Twelve didn't stand a chance.
9 Smartest - H.A.M.M.E.R.
At the end of the Skrull invasion, Osborn took advantage of the situation by killing the Skrull leader on national television. After doing so, Norman was lauded as an American hero and given special access to parts of the US Government.
Heading his own agency dubbed H.A.M.M.E.R., Norman had the power to enact many of his greatest schemes. He then formed the Dark Avengers, a group of villains masquerading as superheroes. Osborn served as the leader of the Dark Avenger, wearing his very own Iron Patriot armor based off of Iron Man's designs.
8 Failure - Pass On The Mantle
Catching Peter Parker off guard, Norman, as the Green Goblin, subdued and kidnapped the crimefighting hero. Goblin's goal this time around wasn't to kill Spider-Man. Instead, he hoped to break down the hero both mentally physically until he was insane enough to become the Green Goblin's successor.
Norman tortured Peter for months. Although he was successful in hurting Peter greatly, Peter never broke. Eventually, Spider-Man rose up and defeated his captor in an epic fist-fight.
7 Smartest - Identity Crisis
After Norman regained control of Oscorp, he decided to buy out the Daily Bugle. Then, using his media connections, Osborn is able to manipulate Spidey into physically beating him in front of some cameras.
To top it all off, Norman frames Spider-Man for murder, making him once again a public menace. During his investigation into clearing his name, Peter creates four superhero aliases to hide his true identity. Although Spider-Man was eventually able to clear his name, he only did so by fabricating false evidence.
6 Failure - Gathering of Five
Joining a mysterious cabal, Osborn is able to participate in the 'Gathering of the Five', a mystical ceremony that endows each participant with a different kind of power. Among the gifts given at the ceremony are Power, Knowledge, Immortality, Death, and Madness.
Norman had joined the cult with the intent of receiving the gift of Power. Instead, he received Madness. After the gathering, Norman's already unstable psyche was shattered by this mystical bestowment. In fact, Osborn's mental state deteriorated so quickly that he couldn't even maintain a coherent thought, and was very easily defeated in his next battle with Spider-Man.
5 Smartest- Clone Saga
The events of the Clone Saga shattered Peter Parker. Upon learning that he had a clone, Peter eventually was able to cope after much conflict. However, later on, after some genetic testing, it was revealed that Peter was, in fact, the clone and not his new partner.
When Osborn was later shown by the mastermind behind the entire conspiracy, it was revealed he had tried to use the events to systematically destroy Peter's life. Osborn had even tampered with the test results and switched them, making it seem as though Ben Reilly (Peter's clone) was actually the original. Upon Ben's death, it was revealed that Peter was actually the original, but at that point, the damage had already been done.
4 Failure - Faking Aunt May's Death
Another event that happened in the Clone Saga was the death of Aunt May. Although a very emotional moment that broke Peter's heart, not all was as it seemed. Aunt May wasn't dead at all.
In fact, the Goblin had kidnapped May and replaced her with a genetically altered actress. For months, Peter lived on believing that his aunt was actually dead. Eventually, Norman sent May to Peter with a device implanted in her head that would detonate a series of devastating gene bombs if removed. Spider-Man was able to easily remove the device safely with the help of Mr. Fantastic.
3 Smartest - Red Goblin
Breaking into an abandoned S.H.I.E.L.D. storage facility, Norman stole and bonded with the Carnage symbiote. The most powerful of all Spider-Man's symbiote enemies, the Carnage symbiote not only bestowed Goblin with all of the enhanced powers of Carnage but also enhanced his own Goblin abilities as well.
Newly dubbed the Red Goblin, Norman became more powerful than he had ever been before. He was even immune to the usual symbiote weaknesses such as sonics and fire that heroes had used to defeat the serial killer supervillain over the years.
2 Failure - Impaling Spider-Man
After murdering Peter Parker's girlfriend, Gwen Stacy, Green Goblin escapes to his hideout. It turns out Spider-Man had followed him there, and the enraged hero fought Norman in a truly epic battle.
Hoping to catch the web-slinger off guard, the Green Goblin had his glider come up behind Spider-Man at a high speed to try an impale the superhero. Using his spider-sense, Peter dodges the glider and it instead impaled Norman, killing him.
1 Smartest - Gwen Stacy and the Bridge
After learning Spider-Man's identity, the Green Goblin kidnapped Peter's girlfriend Gwen Stacy and took her to a bridge. Upon Spider-Man's arrival to the bridge, Norman through Gwen over the side.
Spider-Man dove after his love and caught her with one of his webs. The momentum carrying Gwen was so great that the sudden stop snapped her neck, killing her. Norman Osborn's plan could not have gone any better. Not only did Gwen Stacy die, but it was actually Spidey's own actions that killed her.