Caspian was born to the Captain and First mate of the pirate ship Thalassa. He grew up on the ship, learning the ways of a mariner from the time he could walk. At 21, he was given a ship by his parents as a coming-of-age present, which he captained for 9 years. At this time, he grew bored of his life on-ship and decided to travel on land, taking on work as he could, up to and including occasional hit work. 

On one particular hit, he was assigned to kill Daimine-- a young Sylvari hitman who had abandoned his own kill and run off with a substantial down payment. However, he initially failed in this task and was stalked by his own prey. Daimine spared his life, leading to a game of flirtatious cat-and-mouse that finally ended when his friend Quin ran into gang trouble in Divinity's Reach. Caspian and Daimine at that point teamed up to resolve the trouble and quickly became lovers, much to the dismay of the original hit commissioner, who they then took out together. 

After taking out the original commissioner, Caspian is caught and arrested for the murder, at which point the Order of Whispers buys his billet as they require information that only a pirate would know. After the Battle of Claw Island, he becomes entwined with the growing forces battling Zhaitan, eventually helping Trahearne to forge the Pact and becoming Commander. He starts his own guild, naming it Hope's Legacy, and assembles them as a small elite taskforce that he trusts with private missions.

After Zhaitan's death, he retires as Commander, passing leadership to his guildmate Talæesyn. He heads back to Lion's Arch just as it is under seige by Scarlett. There, he and the guild take on new members and prevent the total destruction of Lion's Arch. 

At this time, Caspian and Daimine retire from the guild as well, leaving on a ship to avoid further conflict and continue their travels together.

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When Mordremoth sends out the call, Daimine is affected and turned, leading Caspian to chase him across Tyria before he can cause too much damage. Remembering the Forgotten Ritual he had seen performed in Arah to give free will back to a Risen chicken, he captures Daimine, drags him to Arah and restores his free will.