Born in Boston, Massachusetts, Jason was not always a malicious psychopath bent on criminal deviancy. After college Macendale studied at MIT for a short while before enlisting in the Marines. It wasn't long before the CIA recognised his talents and gave him training in the arts of assassination and espionage.
Though Macendale was a skilled field operative and an expert marksman the CIA held the opinion that his methods were unorthodox, violent and most of all dangerous. It was because of this that the CIA dismissed his services. Bitter and angry at the world Macendale turned to a life of crime and became Jack O'Lantern.
Life of Crime
As skilled as Macendale was, his first attempts at villainy were all but successful. His first criminal activities led him to battle with the Machine Man, a struggle of which he soon lost. Though defeated, Macendale wasn't about to surrender himself to prison on his first criminal endeavour. In a quick act of deception, Jack O' Lantern simulated a state of comatose in the hope that he would be taken to a hospital rather then a prison cell.
To avoid captivity, Macendale planed to take the medical centre hostage so that he could barter his freedom, that and make a name for himself as in the criminal world. While taking control of the hospital Jack had his first run-in with Spider-Man. Again, although Macendale was well equipped and an expert marksman he was no match for the web-slinger. Realising this, Macendale made his escape, though he would meet and battle Spider-Man many times in the future.
Eventually, Macendale developed a partnership with Ned Leeds, a man who was currently impersonating Hobgoblin. it was during this partnership that Macendale was also hired by the Kingpin as an assassin during the Gang wars. Eventually Macendale's alliances with Hobgoblin were severed as Macendale refused to help Hobgoblin chase down Spider-Man. Seeing as Macendale had lost all respect for the current Hobgoblin and seeing as he had done so much work to aid him, Macendale decided that he would make a much better Hobgoblin than Leeds and hired a foreign assassin to kill him. Macendale took on the role as the new Hobgoblin and stopped wearing the flaming Jack O' Lantern suit.
Getting the suit
During the events of Inferno, Macendale sold his soul to N'Astirh to gain the powers of a demon, but the deal proved to be a bad one as Macendale began to lose control more and more every day to his demonic half. This would lead to battles not only against Spider-Man but also Ghost Rider, Johnny Blaze, and Moon Knight. Ultimately Macendale and the demons inner struggle led to their separation, and the demon split from Jason becoming the Demogoblin. Once more powerless, Macendale obtain the strength formula of Kraven the Hunter, which enables him to easily defeat his demonic doppelganger, before Demogoblin ultimately died saving a young child in battle.
Macendale was defeated once more by Spider-Man along with Coldheart, during an attempt to kidnap Jason's long-lost son. He would remain in jail for some time before being freed by Gaunt, sending him into combat against the Scarlet Spider. In exchange for doing Gaunt's bidding, the scientist turned Macendale into a cyborg, complete with removal of one of Macendale's eyes with a new high-tech cyborgnetic eye. He failed however and was once again arrested.
Jason seemed to be the ultimate incarnation of the Hobgoblin, but upon the return of Roderick Kingsley, who was the first Hobgoblin and was also believed dead, that Kingsley proved to be the superior Hobgoblin, and killed Jason Macendale.