“So when am I allowed to be scared for you, then? At least two guys with guns? How about one guy, with like, a really big gun or half a dozen guys with small guns? Tell me the requirements so I’ll know when it’s allowable to be worried that my husband is going to get a bullet in him?” -Mary Jane, “Five Minutes,” The Ultimate Spider-Man Anthology
"The people I deal with on a daily basis are stone cold killers. This isn't the Godfather where all the bad guys are honorable and misunderstood. In their world there is no code of honor. They're vicious lowlife vermin who would just as soon slit your throat as shake your hand. Especially if they can make a buck while doing it." -Ben Urich, Spider-Man: Made Men, August 1998
I've wondered the same thing as Mary Jane did. A few guys with pistols may not bother Spidey, but at what point does a small mob of average people with guns become a problem? The typical supervillain may not use a firearm but mafia bosses have gangs that certainly do. That brings me to the villains in Spidey's rogues gallery that don't get as much attention as the big name bad guys. In comparison, the mob bosses have less "comic book supervillain appeal" than typical costumed menaces. That or they are painfully corny. Hammerhead has always been my least favorite bad guy and Silvermane is an old man in a iron suit. Then again, aren't a lot of bad guys corny? The Vulture is an odd but respected enemy of Spider-Man’s but is he that different from Silvermane? He definitely gets more attention.
Spider-Man has dealt with many petty crime lords and wannabe mob bosses, none of which seem to make return appearances. The superpowered bosses always come back to their places of power, which, considering the number of superheroes in New York, probably makes powers necessary for a long career. Still, I doubt that desperate or just violent individuals will ever stop trying to organize crime. Super crime lords will always need street level foot soldiers to peddle drugs or guns. So here is my list of mega bosses and the small time gang leaders that they use and discard.
Bedrock Gang
The gang briefly showed up to rob Aunt May and her “in laws,” Mary and Richard Parker. The Parkers had arrived at Liz Osborn’s brownstone to shelter from the “Maximum Carnage” riot when the gang approached them. They were saved by Flash Thompson and Flash was saved by the Molten Man. (First appearance: Spider-Man (Vol.1) #36, July 1993)
Black Alfred
After Wilson Fisk "retired" from organized crime, the lesser gangs began fighting for his territory. The Vulture was making big moves in that direction, killing any small time bosses that didn't fall in line. "Black" Alfred Leroy was an ambitious young criminal that wanted to move his operation out of Harlem and into the rest of the city, becoming the new big boss. Vulture tricked him into killing his rivals, sparing Toomes the trouble. Spider-Man then arrived from the death trap Vulture had set for him, allowing Alfred the chance to escape. The Vulture and his nephew, Malachi, escaped from the burning building but were ambushed by Alfred. Malachi was shot and killed. Vulture turned his rage on Leroy, nearly beating him to death. The police arrived and Vulture fled, leaving Black Alfred to beg the cops to protect him. He has not been seen again. (First appearance: Spectacular Spider-Man (vol. 1) #44, July 1980)
Blackie Gaxton
Gaxton was a small time gangster in Philadelphia that still had a major impact on the life of Betty Brant. Her brother, Bennet, owed Gaxton a lot of money in gambling debt. He was Gaxton’s lawyer and was important in helping the mobster escape prison with the help of Doctor Octopus. Betty took Octavius to Philadelphia and Ock broke Gaxton out for his $100,000 reward. Spider-Man followed Betty to Philadelphia and to the barge they were hiding out. In the fight that followed, Blackie shot at Spidey but one of the bullets hit and killed Bennet. Betty blamed Spider-Man for his death and Spidey attacked Gaxton and his gang so savagely that he flew into a wall. He went back to prison but Bennett’s death meant that Peter could never tell Betty his secret. Gaxton was never released from prison and hasn’t been see again. (First appearance: Amazing Spider-Man (vol. 1) #11, April 1964)
Easy X Gang
Easy X operated out of Brooklyn, the neighborhood of officer Scott Washington. His brother, Derek, was killed in a shooting caused by the gang. Scott was also injured, causing him to lose the use of his legs. He was soon bonded to the four Life Foundation symbiotes and called himself Hybrid. Easy X didn't last long after that. (First appearance: Venom: Along Came a Spider #2, February 1996)
Morris Forelli
Mr. Forelli appeared briefly as Digger (formerly the Vegas Thirteen, assassinated mafia leaders killed in Las Vegas) returned to New York in revenge for their assassinations in 1957. Forelli had ordered the hits and continued to be a monster in New York for decades. He enlisted Spider-Man’s help to protect him, paying him $10,000 per day. During a battle with Digger, Forelli's hitmen arrived to kill the monster and didn't do well. Spidey went back to Forelli's mansion to give him a piece of his mind for sending assassins when Digger arrived and threatened to kill the gangster's daughter. During the fight, Forelli confessed that he had been the one to order the hit in 1957 and Digger promised that his daughter would die anyway. Spider-Man's fight took them into the sewer, where Digger's expended all of his radioactive energy, letting the various gangsters body pieces collapse. Forelli was arrested afterward, as a microphone had heard his confession. (First appearance: Amazing Spider-Man (vol. 2) #52, May 2003)
Don Vincente Paolo Fortunato
After Wilson Fisk left a power vacuum in New York's criminal hierarchy, Don Fortunato tried to step into his place. He was a feared and respected criminal, with parents warning their children to behave or "One Eye" would get them. (He wore a patch over his right eye.) In the end, he was willing to bond his teenage son, Angelo, to the Venom symbiote to make a man out of him. The new Venom attacked Peter Parker but Angelo didn't live long after the bond, as the alien dropped him in mid leap between buildings. Fortunato still smiled, knowing his son didn't die as a nobody. (First appearance: Spider-Man (vol. 1) #70, July 1996)
The Hogan Gang
The Hogan Gang made the mistake of attacking Spider-Man while he was already busy with Kraven the Hunter. The gang attacked both combatants, causing Kraven to snap that "a lion does not run from rabbits!" The gang was swatted aside, but managed to separate the enemies. After Kraven was beaten, he was webbed up for the police, along with the gang. (Amazing Spider-Man (vol. 1) #34, March 1966)
Lucky Lobo
Lobo was unfortunate to draw the attention of Norman Osborn, whose ambition led him to want the gangster’s mob. He originally sent the Headsman to kill Spider-Man, intending to impress the crime boss. Headsman failed and Osborn next approached Lobo as the Green Goblin. Lobo rejected the Goblin’s threat to take over his gang and Osborn decided to use Lobo’s undeclared income against him. He turned the documents over to the Daily Bugle, who turned it over to the police. As the police raided Lobo’s establishments, Goblin prevented all of the goons from escaping. Spider-Man showed up and captured the rest of the gang, despite Lobo offering an alliance against the Goblin. Osborn’s plan failed, as the entire gang had been captured and there was nothing left to control. (First appearance: Amazing Spider-Man (vol. 1) #23, April 1965)
Mr. Morgan
Shortly before Black Alfred made his move, Mr. Morgan tried to leave Harlem and expand into Manhattan. In the power vacuum caused by Kingpin's and Hammerhead's departure, he hoped to take it all. The Vulture was in the early stages of making his own advances into Fisk's territory. One of Mr. Morgan's extortionists had tried to shake down Toomes and was dumped into the Hudson River as a result. Mr. Morgan planned to make a deal with the Vulture and then betray him later. Morgan paid a visit to Toomes' shop and offered him a position in his gang, which insulted him. Vulture left Morgan hanging from a streetlight. This humiliated the gangster, and he swore revenge. Later, the Vulture was battling Spider-Man and a hitman hired by Morgan arrived to kill Spider-Man. He was going to steal the kill that the Vulture wanted so badly. Spidey eventually defeated Toomes and the hitman ended his contract, as killing Spider-Man was pointless with Vulture defeated. Mr. Morgan was never seen again but according to Black Alfred, he ended up in prison. (First appearance: Spectacular Spider-Man (vol. 1) #4, March 1977)
Savage Skulls
The Skulls were based out of the South Bronx and caught the attention of the White Tiger. He caught them trying to steal the car of a local gangster. When Tiger stopped the teenage gang, the mafia boss offered him a job and got knocked on his butt. (Spectacular Spider-Man (vol. 1) #25, December 1978)
Stoneface
Stoneface, real name unknown, was a gangster based out of Harlem that had a paralyzed face after a stroke. He specialized in protection money and number-running, and his numbers runner was Jody Casper. Casper was also the nephew of Sam Wilson, the Falcon. When Casper went to prison for working for Stoneface, it was Captain America that bailed him out, not his boss. Stoneface did assume that his numbers runner had talked to the police and had two leg breakers go to his house. He was saved by his uncle and Cap, who then arrested Stoneface. When he got out of prison, he kidnapped Wilson and demanded $1 million or else the State Office Building that was being constructed would be destroyed by rioters. The kidnapping drew the attention of Cap and Spider-Man, who saved Wilson and captured Stoneface. (Interestingly, there was a real life Harlem gangster named Casper Holstein that ran "numbers rackets" in the 1940s.) (First appearance: Captain America (vol. 1) #134, February 1971)
Gavin Thorpe
Thorpe was a minor gangster that had been away from the family business for some time and personally executed his younger brother after some kind of disappointment. This put the older Thorpe solely in control of the family. When a lieutenant informed him that Spider-Man was a pest to their enterprises, Thorpe decided to deal with him. He never seemed to make his move, but did take part in an assassination attempt against the new mafioso in town, Don Fortunato. The hit failed, and Fortunato actually invited his rivals to join his organization. As he had allied himself with the international terrorist group known as Hydra was going to be very powerful. Spider-Man and Daredevil arrived, and quickly defeated the gangsters. Fortunato's son, Giacomo, had stolen one of Hydra's helicopters and fired its entire payload into his father's home. The heroes and Fortunato escaped, but as Thorpe hasn't been seen again, he was probably killed. (First appearance: Spider-Man (vol. 1) #53, December 1994)
Jason Tso
Jason Tso was an ambitious small time gangster that was at was war with Dr. Octopus (Carolyn Trainer) for virtual reality technology. He was the owner of Club Noir, where Ben Reilly as a waiter. Tso was met by Daily Bugle reporter Ken Ellis, who wanted to speak to him about ties to organized crime. It was then that an assassination attempt was made on Tso, who was saved by Reilly, and later the Scarlet Spider. The attack was all that Ellis needed to tie Tso to crime, and when the gangster read the story in the paper, he order Reilly to intimidate the reporter. However, Ellis was also targeted by Joystick, a participant in The Great Game but was rescued by the Green Goblin (Phil Urich). The Club Noir was badly damaged after being attacked by Doctor Octopus and Tso demanded that Alistaire Smythe use his spider slayer robots in revenge. Tso set up a meeting with Trainer to discuss peace. The meeting was set up at the Central Park Children's Zoo, which soon turned into a mob scene after Smythe's spider-slayers arrived. Trainer's hired guns (Aura, Override and Looter) came to redeem themselves for past failures, setting up a three way fight between them and the Scarlet Spider. Neither the robots or Trainer's thugs defeated the other. Tso planned to double cross Smythe, but was killed by the hitman called "The Pro" before he had the chance. (First appearance: Web of Scarlet Spider #1, November 1995)
As you would think, the human gangsters come and go but the superhuman criminals keep their grip on New York's organized crime. As you've seen, it usually only takes one encounter with a superhuman to take the average mobster out of the game. Other crooks have tried to move into the mafia (Chameleon, Doctor Octopus, the Hobgoblin, Jack O’Lantern, Green Goblin, Black Cat, the Arranger, the Rose, the Lobo brothers) but none of them had staying power. The superior criminals use the lesser mobsters as needed and always come back to power, no matter how many times they are put away.