Macendale attempted to steal the Goblin secret formula for superhuman strength. After failing to do so, he intimated Harry Osborn by threatening Osborn's loved ones for wanting the Goblin formula, resulting in a confrontation between himself and the second Green Goblin where Macendale was overcame. During a demonic invasion of Manhattan, Macendale felt dejected and humiliated. Offering to sell his soul in exchange for a demon's power, the demon N'astirh fused a demon to Macendale. Enhanced by the demon's power but horrified as his handsome face transformed into a demonic one, Macendale blamed his suffering on Spider-Man and Osborn. He hunted Spider-Man down for revenge. With his demonic powers, Macendale defeated Spider-Man easily but Mary Jane Watson intervened before he could deliver the killing blow. Having finally been made into the notorious supervillain he hoped to be at the cost of his humanity, Macendale put his personal enmity for Spider-Man aside and used his demonic powers to be a top contract killer. He offered his mercenary services to Hammerhead and Tombstone to eliminate Robbie Robertson but is stopped by Spider-Man and Puma. Macendale next conspired with Carrion to eliminate Spider-Man before his co-conspirator ultimately nearly took both villains out instead. Macendale goes after Doctor Strange but an illusion spell is cast to try to calm the monstrous man/demon and Macendale sees his true face in reflections of himself. Macendale was later stiff-armed by Doctor Octopus into joining the Sinister Six's second incarnation which twice tried to take over the world, failing due to counter measures by Spider-Man, Hulk, Ghost Rider, the Fantastic Four and many more heroes. As an independent mercenary and criminal, Macendale would clash with many other heroes, including Darkhawk, and Sleepwalker. However, the insane demon who shared his body acts dominate but gets destabilized long enough for Macendale to briefly regain his sanity during conflicts with Spider-Man and other heroes; once involving Moon Knight, and twice involving the two Ghost Riders (Danny Ketch and Johnny Blaze). Macendale ultimately expelled the demon referred to as the Demogoblin out of his body. Despite Richard Fisk want vengeance for Ned Leeds, he has a reluctant partnership with Fisk but later tried to eliminate the Blood Rose and the new Kingpin but is foiled by Spider-Man. In a rare event, Macendale teamed up with Spider-Man to defeat the duo of Demogoblin and Doppelganger. Macendale was hired by the Foreigner to assassinate