The infamous leader of the Red Skull Legion pirate gang, Jonathan Kahn has a well-deserved reputation for debauchery and barbarism. A Wall Street broker who lost everything in the market crash of 1929, Kahn became a pirate to finance his rather extravagant and sordid lifestyle. Kahn is a boozer, brawler, womanizer, scoundrel, liar, cheat, and murderer, with a taste for any number of vices.

Kahn—of the famous Chicago Kahns, a well-to-do family of industrialists—was always something of a black sheep. As a child, he was prone to angry outbursts and anti-social behavior (though he could just as quickly become a perfect gentleman). When he was older, he purchased a medical deferment that kept him out of the Army during the Great War, but learned to fly anyway; he was arrested several times for brawling during this period.

In short, his growing reputation as a brute alienated his family. After the war, Kahn made money peddling fake influenza cures. He later graduated to the "Drake scam," which provided him with a steady income. He told people that the heirs of Sir Francis Drake were going to sue the British Crown for all the gold Sir Francis had captured, and they would be paid ten dollars for every dollar they donated to the lawsuit. Kahn first flew from city to city himself and later hired henchmen to harvest weekly contributions from families, threatening to cut them out of the deal if they didn't keep "donating funds to the legal effort." Kahn invested his ill-gotten gains in the stock market, spreading his wealth around to industrialists and associates who subsequently fell for his other schemes. He bought extensively on margin, made fast trades and even manipulated the press by leaking stories that spiked prices so that he could sell out at a fat profit. His stock market successes did not last, however; the stock market crash ruined him.

Destitute, Kahn cut a deal with the Purple Gang, selling them all future profits from his Drake scam in return for a quick investment in a fleet of planes. The Purple Gang went for the idea, and the Red Skull Legion was born. Shortly after forming the Legion, Kahn and his men flew to Utah as an escort for a zeppelin supposedly full of Mormon refugees from the Industrial States of America, allowing them to slip past the normally diligent Morman defense forces. The zeppelin was actually a Trojan Horse, filled with hordes of armed pirates. Upon landing, the pirates seized the airport while the Red Skull Legion made repeated strafing attacks against the local militia. The landing party moved quickly, damaging local defense stations, and stealing the airship Moroni—later renamed the Machiavelli. Next, Kahn had the Red Skull planes repainted, giving them the colors of Utah's militia. Moving into the People's Collective, the Skulls raided and pillaged, while Collective forces placed blame squarely on Utah. After a profitable period of raiding, Kahn returned to the I.S.A.

Since returning to the I.S.A., Kahn typically attacks only soft but valuable targets. He is surprisingly far-ranging for a pirate, striking into virtually every nation in North America (though his raids within the I.S.A. are reserved for new pirate bands that attempt to compete with him.) While other pirate gangs operate out of the I.S.A., most of them formed at the same time as the Red Skull Legion or have been granted letters of marque; Kahn wisely chooses not to interfere with such groups.

"Genghis" Kahn's primary advantage is his foresight. He typically plans missions and raids thoroughly, to maximize the element of surprise. In addition, he has excellent analytical skills and has an uncanny talent for sniffing out ambushes. Along with his predilection for mayhem and capacity for bloodshed, Kahn and the Red Skull Legion will likely continue to rule the skies over the I.S.A. (at least, until some valiant flyer ends Kahn's reign of terror for good).