Chester is portrayed as a man without desires or goals. Everything he achieves is meaningless to him, turning into nothing seconds after having obtained it. He feels he's alive only on critical moments, those when his life is on the line, but even then its unfulfilling at the end.
During one day he was travelling inside a war-stricken town, he spotted a girl with a doll and remembered his younger days and how he enjoyed playing with dolls. At that moment, he thought on playing at a large scale, using the kingdoms and their leaders as tokens of his own game.
He started his plans convincing the younger member of the Halteese's Royal family, Demuth, to rebel and form a kingdom of his own. He then worked as advisor for Dalkia's queen while serving Demuth as Prime Minister. Chester moved the pieces, assuring Maletta's growing into an independent kingdom while diverting Dalkia's attention towards Grandall. When the time was right, Chester backstabbed Demuth and seized Maletta as his own, but his plans were ultimately foiled by the apparition of the player, who defeated all his units and Chester himself on Chronicle 10.
A year later, Chester appeared as Emperor Strife's advisor and tactician, helping him taking care of the player. Even though Chester planned various officers to kill him, the player defeats every enemy and finally confronts and defeats Chester at Grandall's capital, Parousia, at Chronicle 19. It's unknown whether he was killed or just arrested.