As a pirate captain and swashbuckler, Radley Addington's ship was capsized and himself nearly drowned before he was saved by an enormous and powerful serpent under the dark depths of the crashing waves. Imbuing him with a powerful warlock bond, Radley was returned to the shores of Scoda with the wisdom of the World Serpent guiding him to learn more of the world through traveling with the party. Pursuing the freedom of his own soul, Radley traveled with many adventures through the war in Alpia to the depths of the Underdark beneath the city of stormpeak. After discovering himself through the journey and making a solo voyage through the bay of pirates and to the cliffs of the fortress city of Bastile, Radley met the eccentric aide to the Emperor, Kelak Nilfard. Unbeknownst to him, Kelak was on the run from imperial rule after the party outed him for spying on the emperor. However, with the convincing words of Radley, Kelak was inclined to leave the Infinitum Cult and inform the group about their doings and whereabouts after meeting privately. After traveling under the guidance of Kelak, the party confronted Wugrim Ironfist in the palace of princes within Linhaven, before he was ultimately defeated and let off a cataclysmic eldritch explosion that destroyed the entirety of the palace. Crumbling the rocks above, Radley was crushed to death and left behind as the party narrowly managed to portal themselves to safety.