Originally hired as the Kingpin's enforcer, Macendale soon joined forces with the Rose (a.k.a. Richard Fisk) and the original Hobgoblin (Ned Leeds posing for Roderick Kingsley). However, their coalition was abruptly interrupted when Jack O'Lantern refused to help the Hobgoblin chase down Spider-Man. He then hired the Foreigner to assassinate Ned Leeds so he could take over as the Hobgoblin (just like Kingsley had planned when he spread the word that Leeds was the Hobgoblin). When Spider-Man discovered the body of the Hobgoblin, he pulled away his mask to expose his identity and was stunned when he recognized Ned Leeds. He tried to convince himself that Leeds was innocent but incriminating evidence found at the scene led him to believe that Leeds was indeed the Hobgoblin.

However, it was later revealed that Leeds had been brainwashed into playing the Hobgoblin and that the real culprit was still at large. Unaware at the time that the dead Hobgoblin was an impostor, Macendale started assuming the guise of the Hobgoblin and began wreaking havoc across the city. He soon found out that he had also inherited the Hobgoblin's enemies, notably Spider-Man and the Green Goblin.

At one point, his obsessive craving for power led him to strike a deal with the demon known as N'astirh, who had him possessed and transformed into the Demogoblin. He eventually succeeded into separating himself from the demonic entity and was later implanted with cybernetic devices provided to him by the villain known as Gaunt.

His reign as the Hobgoblin tragically came to an end when he was captured and sent to prison. While in prison, he received a surprise visit from the real Hobgoblin, Roderick Kingsley, who had come back from Europe to assume once again the Hobgoblin identity. Kingsley murdered Macendale because he felt that latter had brought unwanted publicity with the announcement that Ned Leeds was the original Hobgoblin and since the public at large had always assumed that only one person had ever been the Hobgoblin, the resulting uproar had threatened to uncover the unsavory business practices of Kingsley's corporation. To learn what Kingsley has done since he murdered Macendale, please read Spider-Man: Hobgoblin Lives #1-3 and Spectacular Spider-Man #259-261 for the most recent information about his current whereabouts.