Nothing is known of the life of Charles Halstead before he became a linotyper at the Daily Courier. A long-time employee, Halstead was a friend and favorite of publisher Rex Morgan. Secretly, however, Halstead was frustrated with his lack of advancement at the paper and at some point, snapped. He resolved to take what he had never been able to earn and his first target was the paper itself. He began to stage a series of crimes based on emotions (hate, greed, etc.), clueing the Courier with leads to his crimes. As time passed, Halstead, as the Psycho-Pirate, became bolder. He penned a letter to the Courier, challenging the Justice Society to stop a new wave of crimes based on a variety of emotions. For example, he engendered fear into the inhabitants of a city where he threatened to unleash a deadly plague until his plan was halted by Dr. Mid-Nite. Each JSAer was given an emotion and a task to solve. With the JSA dispersed and only the Atom to guard Halstead, the Psycho-Pirate began a campaign to demoralize the publisher with constant news of despair: business failure, divorce, foreclosure - a series of lies designed to crush the spirit of his employer. To remove the Atom, he convinced the hero that the JSA had been captured and sent the Mighty Mite to rescue them. The Atom discovered the ruse and defeated the criminal's henchmen disguised as JSAers. In doing so, the Atom discovered the true identity of the Psycho-Pirate, who shot him to preserve his secrecy. Wounded, the Atom made it to the Courier just as the JSA returned and exposed Halstead as the Psycho-Pirate. Halstead was subsequently sentenced to a length prison term (All-Star Comics #23).

    Two years after his initial arrest, the Pirate escaped from prison with the aid of cellmate "Big Mike" Carillo. Carillo, a petty hecnhman, had been captured by the JSA under as yet unrevealed circumstances and wanted revenge. Planting his wallet on the unsuspecting Johnny Thunder, "Big Mike" arranged for the JSA to be privy to the plans he and the Psycho-Pirate had laid. Again basing his crimes on emotion, the Psycho-Pirate plans led the JSA through a gamut of sensations from pride to anger. Unfortunate for the crime-master, his less the brilliant aide had planted a wallet containing not only the plans, but his address as well. After completing the various tasks, the JSA converged on the criminals' hideout and the Psycho-Pirate was once again sent to prison (All-Star Comics #32).

Partial records indicated that the Psycho-Pirate is known to have had at least one more case against the Justice Society (unpublished All-Star Comics) before the dissolution of the group in which he created the fictitious character of William Wilson and sent the JSA on a wide-ranging search for a series of artifacts.  When they returned, the Psycho-Pirate revealed that he was both  the fictional deceased as well as the supposed inheritor and had created the entire scheme to trick the JSA into acquiring wealth for him while restoring in confidence after they had repeatedly defeated him.  (Unpublished All-Star Comics).  His activities afterwards prior to his death are unknown.

    After some years in prison, Halstead's health began to fail. Spending the last years of his life obsessively researching the mysticism of emotions, the elder criminal became aware of the Masks of Medusa. The masks contained vast powers of emotional manipulation, allowing the wearing to project any emotion he could express. Determined to have a legacy, Halstead passed this information on to his cell-mate Roger Hayden, a gangster who eventually used the masks to become the second Psycho-Pirate (Showacse #56). Halstead died sometime in the late 1960's.