Jack O'Lantern was the original alter ego of Jason Macendale. He wore a flaming pumpkin mask and flew on a disc glider. His first appearance was in Machine Man #19. He battled the aforementioned hero and was soundly defeated.
He later moved to make a permanent home in the family of Spider-Man villains, beginning with Spectacular Spider-Man #56. He had no super powers, hurling explosive grenades and hopping about on a "pogo platform".
He was a minor villain in Spidey's rogues gallery until he formed an emnity with one of The Hobgoblin's mind-controlled "stand-ins", Ned Leeds. Macendale wished to increase his underworld status and fearing the Leeds/Hobgoblin, hired assasins to kill the Goblin and took his arsenal for himself. As a Hobgoblin, Macendale failed to make any greater mark upon the Underworld. He made various bizarre efforts to increase his threat-level, including pacts with demons, ingesting weird alchemies stolen from Kraven the Hunter's lineage, and cybernetic implants provided by Norman Osborn. During this time, he would on least one occasion, attempt to rob a bank wearing his Jack O'Lantern armor, during which effort he was jailed and questioned by SHIELD as related in the Secret War miniseries.
Macendale was later killed by Roderick Kingsley, the true Hobgoblin, who had allowed Macendale his claim on the goblin "franchise" to further hide his identity as the power behind the various incarnations of the Hobgoblin.
As the "second" Hobgoblin, Macendale was a member of several collections of Spider-Man's enemies, including the Sinister Six.