Ulysses Hadrian Armstrong was a psychotic child with the mind of a military genius. Bored with his life at a military school, he reads books about military history. Ulysses later scares the bullies that pick on him into helping him to escape the school, and work as his henchmen; he travels to Gotham City to recruit gang members into his "army". Utilizing his military skill, he launches a direct attack on Black Mask's gang, which gains him the nickname "The General". Ulysses dresses himself and his henchmen - primarily the remnants of gangs he has conquered - in historical attire as they act out crimes based on military history.
While his father, sister and brother knew of his psychosis and the threat he poses, his mother was blind with affection for him, even as he is being hauled into juvenile hall after his crimes are foiled by Batman.
The General has teamed up with other costumed criminals, including a henchman of Maxie Zeus known as Julius Caesar. Picking up the delusional criminal in a museum, he brought Caesar to his home (much to the dismay of his father). Wanting even more membership, the General and Caesar use a stolen circus lion to threaten a biker group known as "Los Bandidos" into becoming their henchmen. A fight erupts between the biker gangs, but is stopped quickly by Robin and a combo of hisetective skills, intel from the General's sister, and the help of Sheriff Shotgun Smith. Meanwhile, the General and Caesar steal money from the bank, hijack a police car and would have gotten away but for Robin's intervention. The General then went to jail for a number of weeks.
Several weeks later, the General teamed up with Toyman, as they plan to steal a toy collection made by Schott from a collector. Robin tracks them down to the collector's house, only to find Schott (a homicidal maniac who hates kids to begin with) pointing a gun at Ulysses. The General saves himself using an automized panzer toy, a train, and help from the Boy Wonder. After the two crooks were caught, Ulysses claimed that Toyman made him do it and only serves a brief sentence in prison.
Once out, he meets the pre-teenaged ruler of an Middle Eastern country, and they become fast friends. Deciding to help the ruler thwart his enemies, the General travels to his aquaintance's home country, and wages war. Hiring four dangerous mercenaries - Gunhawk, the NKVDemon, Hatchet, and Deadline - and using a vast army, Ulysses was on the brink of comitting genocide when Robin and Nightwing arrived. Robin stops the mercenaries, and was about to grab the General when he noticed how unhappy his "friend" was with the General for starting a war. Now a slave, the General spends several years scrubbing floors and cleaning palaces.
After a very long absence, the General returned to Gotham City, having aged several years, grown several feet, and become a more formidable hand-to-hand combatant. For reasons yet unknown, he was hired by Spoiler to gather information about the gang wars, and find a possible solution to them. He continues to hold a grudge against Robin and betrays Spoiler. Spoiler survives a gunshot to the shoulder, and then distracts him long enough to get the drop on him and escape.
He later comes into possession of the Red Robin costume worn by Jason Todd, and uses it as part of a campaign of psychological warfare against Tim Drake. More formidable than ever, he is revealed to be holding Lonnie Machin, an anarchist vigilante, hostage while commandeering his identity as "Anarky". Where Machin's approach as Anarky had been to cause social change, Armstrong's approach bordered more on psychotic and meaningless acts of chaos and destruction.
Armstrong managed to catch Robin in his warehouse; Robin escapes through unknown means, but not without sustaining serious burns to his head. Soon after, a final confrontation ensues, where Anarky attempts to kill all of Gotham City's gangs, so as to create more violence. The combined efforts of Robin, Spoiler, Commissioner Gordon, Officer Jamie Harper and the Gotham Gangs, results in Armstrong's defeat. In order to take the edge off of Armstrong, Robin asked Officer Harper to bring the Armstrong family to confront Ulysses. Unfortunately, while the action worked, Armstrong caused a bomb to explode, killing his brother and sister in the blast. Armstrong blames Robin for their deaths.
Managing to escape from the police, Armstrong returns to his hideout, where he has Lonnie Machin paralyzed. There, the pair of them argue about the true meaning of anarchy; Ulysses states he could create enough anarchy with only one question: "Who is Robin?"