The Sinister Syndicate's original incarnation consisted of the Beetle, Rhino, Speed Demon, Hydro-Man & Boomerang. They battled Spider-Man, Silver Sable & the Sandman at Coney Island.
The Syndicate originally were hired by the criminal mercenary Jack O'Lantern (Macendale) to kill Spider-Man and Silver Sable. Most of how the five criminals came together is unrevealed, but there is a strong possibility most of them knew each other from working as hired muscle for Justin Hammer. They ambushed Spider-Man and Sable at Coney Island, and almost succeeded on their first assignment, if it were not for the timely intervention of the recently reformed Spider-Man foe the Sandman, who was boarding up with a family that lived nearby and was licking his chops to trade blows with Syndicate member Hydro-Man, who was a hated enemy. Despite this setback, all five of the criminals managed to escape. In the end, the long lasting effects of the attack were a concussion for Spidey thanks to a charging Rhino, Two sprained ankles for Silver Sable who foolishly tried to knock out the armored Beetle using a well placed diving kick and the destruction of the world famous roller coaster the Cyclone, which has since been rebuilt.
Major Story Arcs
Hired by Doctor Octopus
With their reputation now in question, the group next took an assignment in the small Balkan country of Belgriun working for fellow Spider-Man enemy Doctor Octopus to help overthrow the Monarch of the country and in doing so posing as heroes of the people. Already you can see the foreshadowing of things to come for the group, such as in-fighting and selfish arrogance. The Beetle shows signs of doubt about his role as a villain, and Boomerang clearly questions the Beetle's leadership of the group every step of the way, thinking himself to be a better choice to lead. The Speed Demon is clearly trying to push the rest of the team's buttons especially Boomerang and Hydro-Man. Spider-Man, Silver Sable and the Sandman, now working freelance for Sable, all are dispatched to Belgriun to take down the Syndicate. Early on the Syndicate gain the upper hand, attacking Spidey and chaining him down. This victory, however, is short lived as Spidey takes out Boomerang first, then Sable takes down Hydro-Man and Sandman defeats the Rhino. With the assignment a bust, the Beetle manages to barely escape as does Speed Demon. Hydro-Man suffered an electrocution at the hands of a falling chandelier and is either captured or reforms himself later and manages to escape. The Rhino was knocked unconscious by the Sandman and is presumably taken into custody. Boomerang was slipped knock out gas by Sable(done off panel) and taken to a local hospital. It is presumed he is then arrested.
After the group takes a hiatus to pursue solo ventures, the group once again is reformed by the Beetle, who having been recently released from prison and in debt to such figures as the Kingpin and the Tinkerer, needs the extra muscle to succeed in paying them back. From the get-go, Boomerang once again tries to stir the pot and reminds The Beetle of their past failures under his leadership. Rhino keeps the peace and tells Boomerang to be quiet and listen to Jenkins. The group then plan a bank robbery which is interrupted by Spider-Man. The group quickly gain the upper hand on the wall crawler and actually are about to deliver the killing blow when the Rhino steps in and lets the others know he does not want to be an accessory to murder as he only wants to make enough money so he can remove his hide, which is now permanently bonded to his body. The group begrudgingly agrees and moves on with the escape. However, Boomerang decides to go back inside the bank to finish the job and ends up being captured by Spider-Man. Leila Davis, who Boomerang was dating at the time, served as the Syndicate's get away driver and the Beetle forces her to drive away due to the swarm of cops and Boomerang's defiance. Soon, the others learn about the Beetle's debts and how the first heist was entirely owed and taken by the Kingpin. This now puts a damper on the groups loyalty to Jenkins, but they agree to let him live. The group then decides their next course of action, either attempt to spring Boomerang from prison or hire a lawyer for him.
After an unsuccessful attempt to spring Boomerang from prison, The Beetle begins to show a lack of confidence in his abilities to lead the Syndicate in front of Boomerang's girlfriend Leila Davis, who secretly has an ulterior motive to joining up with the group: revenge on the Beetle for humiliating her husband, Anthony Davis. Davis was also known as the deceased super criminal the Ringer, who the Beetle used as a pawn in a scheme to defeat Spider-Man. He was murdered by the Scourge of the Underworld but Leila believed it would never have happened if Beetle hadn't made him feel so useless. After a vote by the rest of the team, the majority agree to hire Boomerang a lawyer. The name of the lawyer is Mr. Partridge, whom Jenkins had used in previous incarcerations. During this time the group is beginning to take shape. Speed Demon secretly goes to the Beetle, asking if maybe he could deliberately sabotage Boomerang's case, with the Beetle commenting that he is aware that Speed Demon is clearly trying to put the moves on Leila.The Rhino is promising after one last big score he will leave the team, a move that the Beetle realizes he cannot afford. The aimless Hydro Man is clearly just in it for the wealth and power and strikes up a friendship with the Speed Demon. The next heist the Syndicate pull is an armored car theft, which is highly successful. Behind the scenes, Leila Davis visits the Kingpin to see what she can do to correct her boyfriend's situation. Boomerang's lawyer Partridge deliberately sabotages his case in court, and the Syndicate move in to free him. They are unsuccessful in their attempt to free him in a court room brawl however, and barely manage to escape amidst the timely intervention of Spider-Man and a group of Guardsmen.
A new Sinister Syndicate was assembled by the new Beetle, Janice Lincoln. They first debuted by saving the new Electro, Francine Frye, as their sixth member. As Beetle explained, organized crime had the worst gender disparity of every profession. She wanted the new Syndicate to respect the contributions of women to evil and foster support among a community of female supervillains. They were going to smash the glass ceiling with the bodies of their enemies. The rest of the team was made up of Lady Octopus, Scorpia, White Rabbit, and Trapstr.
Their first target was Boomerang, a former teammate of Beetle. He had recently made a fool of Electro, and they chose him to convince Electro to join. They attack Boomerang at FEAST, where he was trying to be a hero, and take him back to their hideout. Unfortunately, FEAST was where Aunt May worked so Spider-Man was never too far away. He was able to track them, but Mayor Kingpin and his cops beat him there. In the fight, Spidey was able to take off with Boomerang.
The team was often getting into trouble thanks to Beetle’s relationship with Randy Robertson. Randy wanted her to stop being a villain, so she had made a deal with Kingpin to give up Boomerang to become deputized as his security detail. Her team passed on the idea though. They laid low after that, until the Beetle and Randy were kidnapped by Madame Masque and Crime-Master, who were working with a network of crime bosses brought together by Kingpin. The team showed up to rescue Beetle, who was already in the midst of being rescued by Beetle and Randy’s fathers, Tombstone and Robbie Robertson.
While discussing the membership of a possible seventh member, Ana Kravinoff, the Syndicate is approached by Kindred and sent to a graveyard, where Spider-Man is already fighting off two other supervillain groups. There, Kindred announces they were all hellbound villains who could earn a spot as Kindred's assistant, avoiding torture in the afterlife, if they killed Spider-Man. Spider-Man tries to get away while they all fight each other for the chance, but he fails. Eventually, Doc Ock uses a piece of Black Ant's helmet to knock everyone, including the Syndicate, out through the ear centipedes Kindred was using to control them.
Beetle leads the Syndicate to steal servers full of cryptocurrency dollars from Crytpo-Corp. During their getaway, they are confronted by three Spider-Heroes: Peter Parker, Miles Morales, and Gwen Stacy. They were forced to retreat without their loot. Beetle attempted to fire the whole team for incompetence, but when they threw their employment contracts back in her face, especially the part about their severance, Beetle had enough and just quit, leaving it all to the team.
If she was going to go solo, she needed a quick influx of cash. She tried stealing precious metals from a lab at ESU on the same day Miles was touring the campus. They get into a fight, which turns into a rescue mission when Beetle's wings are damaged and can no longer carry her weight. While composing themselves after the dramatic fall, Beetle is saved yet again by the Syndicate, who didn't know about all the paperwork that Beetle does.
After Hammerhead incites a gang war, Beetle gets the Syndicate back together (less Francine who was arrested and put on the Cape-Killers) to protect her father's territory after Tombstone was gravely injured. He recovered, but Francine was already too deep. The Syndicate was going to take Diamondback's half of Harlem.