For several years, the Arranger was a trusted assistant and faithful advisor to the Kingpin of Crime, overseeing his various illegal business dealings. One of his first tasks involved hiring the Enforcers to organize the Kingpin's Brooklyn extortion operations. Spider-Man and the Sandman tackled the gang, and left the Arranger webbed for the police. Despite this failure, he soon became the Kingpin's right hand man, handling Fisk's public relations while organizing his daily criminal activities. When the Beyonder turned an entire skyscraper into gold, the Kingpin secured millions in gold typewriters in exchange for the discreet removal of the building in order to prevent the world economy from crashing. Meanwhile, Silkworth arranged to seize the government transport ships that were dumping the building into the Puerto Rican trench, but Spider-Man foiled this operation. The Arranger returned to face increasing tension from rogue criminals the Rose and Hobgoblin. After Daredevil defeated the Kingpin, Fisk went into hiding, leaving the Arranger in charge of the organization. A massive gang war erupted. The Arranger allied himself with the Rose (Richard Fisk), Hobgoblin (Ned Leeds), and Jack O'Lantern (Jason Macendale) against the forces of Hammerhead, Silvermane, and the Blue Boys. Saved from the Punisher by Spider-Man's interference, the Arranger worked with the authorities to allow the Kingpin to return to power, ending the war while using Spider-Man as their pawn.

Seeking new talent, the Arranger hired Philadelphia mobster Tombstone and the mutant Roland Rayburn, the Persuader. Silkworth had Tombstone lure the Punisher out of hiding. The Arranger and the Persuader captured the Punisher, though Tombstone was ultimately defeated by Spider-Man. The Arranger's foothold in the Kingpin's empire began to slip when he botched an assassination attempt using the Persuader-controlled Punisher against South Texan gang leaders, the werewolf Lobo Brothers, inspiring a bloody Lobo campaign against Fisk. Nearly killed by Carlos Lobo, the Arranger played on Spider-Man's sense of responsibility to enlist the hero's secret aid against the Lobos. The Lobos were defeated, but the Kingpin was not pleased with his losses.

The Arranger later recruited assassin Richard von Burian (the Sniper), and arranged the reconstruction of the assassin Damage into a cyborg to stop the Punisher's interference in the Kingpin's operations. The Punisher and Wolverine finished both agents. After the Lobo war, the loss of mob territory to Hammerhead and the Chameleon, and failing to trick the Beetle into killing Spider-Man, the Arranger realized the Kingpin would not tolerate his incompetence. Desperate, he begged Spider-Man for help. The Kingpin hired British super-powered assassins Knight and Fogg to kill the Arranger. Spider-Man was too late to save Silkworth, but sought justice against his killers.