The Crimson King always wins.
The Crimson King, also known as "King Crimson" or simply "the King," is the enigmatic and secretive ruler of Mercer Island and holds the highest position in the House of Devane.
Much of the Crimson King's past is a mystery. Originally from the Boneyard, until they age of twenty-five, he was a nobody. It was then that he left on a mission with Edward Swallow, Joshua Graham, Bill Calhoun and six other Followers on an expedition. They were captured by the Blackfoot tribe. Swallow negotiated their release, starting his path towards becoming Caesar. Joshua Graham and Bill Calhoun joined him, but when the other Followers refused ,they were executed, except for the man who would on day be the Crimson King. Some how surviving, he returned to the Boneyard after Bill Calhoun. He developed an unhealthy obsession with defeating Caesar, and when years later the missives sent south by the 'Wizard' of the Royal Wasteland reached him. The King, still a man obsessed, became fascinated by the Prophecy of Four, and believed it could some how be the key to fighting Caesar. He gathered three Followers to join him and headed north to Seattle.
The King arrived in the Royal Wasteland and went to the Issaquah, the original writers of the Prophecy of Four. Having taught himself Sammamish, the Issaquah language, the Crimson King learned the Prophecy in it's original tongue from the Issaquah Elder. Deciding to 'place himself' over kings first, since that's what he wanted to do with Caesar, he went to Mercer Island and was welcomed by the 'Wizard,' a man quite clearly off his rocker. The King, believing the first step in the Prophecy was to seize control of the established House of Devane and thus become a monarch, challenged the 'Wizard' to a duel. The 'Wizard' agreed, believing himself unbeatable, and King, a good hand with a sword as a result of his interest with history and thus had taught himself sword-fighting, killed the 'Wizard' quite brutally. He and his three Followers seized control of Mercer Island and the House of Devane. However, their progress in completing the Prophecy stopped there. One of his Followers joined the Cause and became it's leader, another went on to found Beacon Enterprises. The third stayed on as the King's advisor, being the first "Yellow Jester." Together they tried to advance the Prophecy, but were incapable of doing so, and eventually their union dissolved. The Yellow Jester died of a heart attack thirty years later, and the Causer was killed in action.
When the Outsiders first meet the Crimson King, he is playing the part of the "Yellow Jester," and only reveals himself Timothy Ashford guesses his identity. In a following conversation, the King reveals information on his past, the Wasteland, and Kheiro to Tim. He admired Tim's level-headedness and quick thinking and, since part of the Prophecy says those involved must 'place themselves over kings,' asks Tim to be his successor. Tim agreed, and the King told him to return once his mission is complete.