King Awesome was once part of a group of wastelanders, trying to improve the quality of life in Hoofington. The group consisted of himself, Dawn, Keeper, Big Daddy and Silver Stripe. The group began to fracture when they had disagreements on how to help Hoofington, resulting in the group breaking up when Dawn left to marry Sky Striker and join the Thunderhead Enclave.
King Awesome eventually took over The Society, who at the time were little more than a gang of slavers. He has been running the organization ever since, he took over and helped gradually reform The Society. He has still had encounters with his old friends, now leaders of their own factions and notably sold Pisces and Capricorn to Silver Stripe.
King Awesome was seeking some way of extending his life, he sent Prince Splendid to the Fluttershy Medical Center, which lead to The Society jointly running the building with the Collegiate. King Awesome meets Blackjack when she arrives to borrow the Society's airship. The two talk about his actions, including the serfdom he has setup and his views on the society and what he sees them as eventually becoming i.e, old holdovers much like the nobles in pre-war Equestria.
King Awesome reveals his collection of O.I.A. related material, including collections of memory orbs, granting Blackjack access to some of his collection. After returning from a visit to a wartime factory with Rampage and Deus, Blackjack and her companions discuss what Blackjack should do, if anything at all. Prince Splendid interrupts their conversation, revealing that King Awesome has passed on due to old age, before crowning Blackjack the new Queen of the Society.