Spider-Man has a lot of powers in Marvel Comics, but he also has some weaknesses. One of his biggest weaknesses is seeing the best in everyone and trusting people a little too much. While some of these people deserve his trust, there are others who he might have been smarter to be cautious around. That makes the moments when someone whom Spider-Man trusts betrays him so heartbreaking to read. It is even worse when that person is someone who means a lot to Spider-Man and forces him to wonder if he should ever trust anyone again.
There have been several times when someone Spider-Man trusted above all others betrayed him, destroying his faith in humanity.
5) Captain America
If there is anyone who Spider-Man trusts over almost anyone else, it is Captain America, and this is true for most of the Marvel Universe. That makes Captain America’s betrayal of everything he believes in so hard for Spider-Man to accept. This happened in the “Secret Empire” storyline, which started in Captain America: Steve Rogers #1 (2016) by Nick Spencer and Jesus Saiz, when Captain America said “Hail Hydra.” This led to Captain America being revealed as a lifelong Hydra sleeper agent.
Of course, this wasn’t the real Captain America, and it was a Steve Rogers from an alternate Earth who was raised as a Hydra sympathizer in a world where the sentient Cosmic Cube child Kobik eventually led this Captain America to take over the country. This hurt Spider-Man deeply because he looked at Captain America as the one superhero he always weighed himself against. With Earth-616 Steve Rogers surviving in Kobik’s mind, Captain America fought back and returned to end the threat.
4) Robbie Robertson
Robbie Robertson had a dark past with the crime lord Tombstone. During the “Tombstone Saga” in The Spectacular Spider-Man #139-#142 (1988) by Gerry Conway and Sal Buscema, it was shown that when Robbie was younger, he saw Tombstone kill someone, and he kept his knowledge of the murder a secret for 20 years out of fear for his own life. This shook Spider-Man’s faith in Robbie, whom he had always looked up to, and he realized that Robbie was guilty of a crime because of his silence.
However, Robbie then betrayed Spider-Man personally after he was sent to prison for being an accessory to the murder by hiding it. In The Spectacular Spider-Man #155, Randy Robertson called for Spider-Man to come help his dad in the prison. However, it was a trap, and when Spider-Man got there, Tombstone attacked him, and Robbie injected him with a drug to knock him out. This hurt Spider-Man more than anything, but in the end, Robbie made up for it by attacking Tombstone and saving Spider-Man in a moment that looked like a self-sacrifice.
3) Boomerang
Spider-Man never should have trusted Boomerang, but the fact is that Boomerang had a personality that sucked Spider-Man in. This all started when Fred Myers (Boomerang) became roommates with Randy Robertson and Peter Parker in Amazing Spider-Man (2018) #1 by Nick Spencer and Ryan Ottley. Throughout the next three years of comics, Fred and Peter became genuine friends, and Fred even tried to turn his life around and be a hero for Spider-Man.
Of course, it was not meant to be. Eventually, during the storyline with the Lifeline Tablet, Boomerang betrayed Spider-Man for the Kingpin and revealed he was working for the Kingpin the entire time. Boomerang didn’t have a choice in the end, and he left a note for Peter and apologized for what he did. However, the note also made things worse by revealing it was a long con and their friendship was faked at the start, although both men became real friends before the betrayal. Boomerang made up for it in the “Sinister War” storyline when he sacrificed himself to save Spider-Man from Morlun.
2) Iron Man
During the “Civil War” event, heroes turned on each other at the drop of a hat. In the case of Iron Man, he had become a mentor and almost a father figure for Spider-Man. He built Spider-Man the Iron Spider Armor. Peter Parker was living in Avengers Tower with Mary Jane Watson and Aunt May, and Spider-Man believed what Iron Man was selling with the Superhero Registration Act. Iron Man even convinced Spider-Man to unmask on live TV to show how much he supported the act.
Things changed when Spider-Man realized Iron Man was tracking him with a device he built into his suit and was imprisoning any unregistered heroes without trial in the Negative Zone. When Spider-Man said he couldn’t support him anymore, Iron Man sent registered villains to track down Spider-Man and attack him. Spider-Man’s unmasking also led to Aunt May getting shot, and Spider-Man realized trusting Iron Man was the worst decision he could have made.
1) Harry Osborn
The biggest early betrayal in Spider-Man comic books came when his best friend turned on him and became the second Green Goblin. This betrayal happened for several reasons, but when Harry Osborn betrayed Spider-Man, it proved that the hero couldn’t trust anyone around him at all. Harry’s father was the original Green Goblin, and no one knew for the longest time. After Norman Osborn caused Gwen Stacy’s death, Spider-Man sought revenge, and Norman died. Harry found out what happened, and he blamed Spider-Man.
When Harry realized that Peter Parker, his own best friend, was Spider-Man and was responsible for his father’s death, he sought revenge against Peter and became the Green Goblin to do so. However, Harry had troubles other than this. He was cursed from birth, and he was dealing with addiction issues, leading to his mind breaking before he turned evil. The tragic payoff came in The Spectacular Spider-Man #200 by J.M. DeMatteis and Sal Buscema, where Harry realized what he was doing and sacrificed his life to save Spider-Man, dying at the end of that issue.