Spider-Man: Brand New Day looks like the main villains will be street-level gang members and mafia bosses, adapting the Gang Wars storyline from Marvel Comics. This comes from the fact that several rumored and confirmed villains, from Scorpion and The Negative Man to Tombstone, are likely to be in it as Spider-Man tries to protect the city from more street-level threats, earning his famous nickname of The Friendly Neighborhood Spider-Man rather than the global and cosmic threats from the last two movies. This makes one wonder what gang bosses might be in the film, and Spider-Man comics have plenty to choose from.
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From the most dangerous crime boss of them all to one of Spider-Man’s most complicated villains, here are the most powerful gang-level crime bosses the Wall Crawler has ever had to face.
7) The Rose

The Rose is an obscure Spider-Man villain, but he has a very famous lineage. Rose is Richard Fisk, the son of Wilson Fisk, the Kingpin of Crime. When he was a student, he learned his father’s criminal secrets and disappeared for years. Most people believed he had died, but when he returned as RFose, he planned to try to take over his father’s spot as the ruler of the criminal underworld. He even caused Kingpin to suffer a breakdown before he finally came around and made peace with his family. Rose ended up dying, but his father used the Life and Destiny and Death and Entropy Tablets to resurrect his son.
6) The Big Man

Big Man was the first mob boss that Spider-Man ever fought in comics. The villain appeared for the first time in Amazing Spider-Man #10 as one of Spider-Man’s first-year villains. At the time, he was a masked man who led a group called The Enforcers, which included Montana, Fancy Dan, and Ox. They were career criminals and henchmen hired by Big Man to work for him. Secretly, he was Frederick Foswell, a reporter for the Daily Bugle, but he turned to a life of crime. When his time on top came to an end, he became an underworld informant who had dreams of taking Wilson Fisk’s spot as the Kingpin, but he ended up working for Fisk before he died protecting J. Jonah Jameson.
5) Hammerhead

Hammerhead has always been one of the most notable of the mob bosses that Spider-Man faces in his comics. Of all the Maggia crime bosses, Hammerhead is one of the most brutal, patterning his look and attitude after the classic 1920s mobsters. However, the one difference is that his head is completely flat, thanks to almost dying and having his skull rebuilt with steel to protect him from further injury. He has been involved in most of the gang wars, including battling Doctor Octopus early on and actually taking control as the new Kingpin when Wilson Fisk was the Mayor of New York City.
4) Hobgoblin

One of the best Spider-Man storylines concerned the arrival of a new villain who remained a complete mystery. He was called the Hobgoblin, and while he was similar to the Green Goblin, the most significant selling point of the character was that his identity was never revealed, and fans began to speculate on who he was. There was a letdown when it was shown to be Peter Parker’s friend, Ned Leeds, although that was later retconned as a trick, and it was really a new character named Roderick Kingsley. While Hobgoblin has been disappointing in many later stories, he is still a very powerful mob boss in Spider-Man’s world, and his recent return is an attempt to rehabilitate the character.
3) Mister Negative

Mister Negative is a fantastic character for many reasons. The character received a new lease on life thanks to the Spider-Man video games, but in the comics, he was also great, as Martin Li was a seemingly good and generous man, but when the Darkforce overcomes him, he becomes as evil as a villain can get. He got his powers from the same drugs that affected Cloak and Dagger, but he has a mix of the light and dark, and he uses them for pure evil. He is also a powerful mob leader, although the men he leads are almost always the Inner Demons, who exist just to serve him.
2) Tombstone

Tombstone is one of Spider-Man’s most dangerous villains when it comes to the crime lords. Tombstone is Alonzo Lincoln, an albino man who has a long, complicated history with Peter Parker’s mentor, Joe Robertson. He has superhuman powers thanks to the chemical Diox-3, which gave him superhuman strength, reflexes, stamina, and durability. However, he is also a brilliant and cunning crime boss, with leadership skills rivaling even those of Kingpin. He also has a complicated relationship with Spider-Man, as his daughter is Janice Lincoln, the new Beetle, who is engaged to Peter Parker’s close friend and Joe Robertson’s son, Randy.
1) The Kingpin

While most people connect the Kingpin with Daredevil, he actually made his debut in Amazing Spider-Man #50. One of the most famous Spider-Man covers of all time shows him putting his costume in a trash can and quitting, and that was because of the torment he received at the hands of Wilson Fisk, who has almost always seemed above the law. Fisk has always set out to hurt and damage the repuation of Spider-Man, and he is one of the only villains, crime lords or otherwise, that Spider-Man has never really been able to beat and keep him down.
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