In The Garden, Gabriel Santiago, Echo and Hope Diyoza encounter Orlando on Skyring centuries after Hope left. Though confused by Orlando's insanity, Hope recognizes that he is one of the the Disciples' unbelievers and states that they need to protect him for the next five years until the Disciples return for Orlando so that they can use the opportunity to follow the Disciples back to Bardo. The three chase Orlando back to his home where they find the chess game that he has set up with the corpses. Orlando fearfully mutters about failing to protect Hope, apologizing to Dev's corpse for his failure and for letting the group into his home. Orlando is scared off when Gabriel recognizes one of the corpses as belonging to that of his friend Doctor Colin Benson from Eligius III.
Orlando later returns to the cabin where he finds Gabriel's computer which displays the Memory Drive recording of the Temporal Anomaly. Though Hope tries to convince Orlando, who continues ranting about his failure to protect her, of her identity and that they can go to Bardo together, in his maddened state Orlando fails to recognize Hope and is too afraid to defy the Disciples' orders that he remain on Skyring for five years. Orlando smashes the computer and runs off, destroying their chances of using the Memory Drive to get the code to active the Anomaly to Bardo.
In Hesperides, Orlando is attacked by an angry Gabriel before running off. As they need him for their plan, the three begin trying to lure Orlando in by settling down and living a regular life together. After a few months, a much more sane Orlando approaches Echo to offer her pumpkin seeds for the garden. However, while Echo goes to retrieve Hope, Gabriel arrives home and his appearance frightens off Orlando.
In a second effort to draw Orlando in, Hope swims out into the middle of the lake and pretends to be drowning. Playing his chess game with the corpses, Orlando hears her screams and rushes to Hope's rescue. Afterwards, Orlando sits down to eat with Gabriel, Echo and Hope who learn that he is a Level 12 Disciple who was banished for failing to take a day of rest. Gabriel questions Orlando about the Disciples' connection to Eligius III, but Orlando orders him not to speak the Shepherd's name. Hope tells Orlando about Dev, who was a Level 7 Disciple and their plan to ambush the group that came back for Dev on his Penance Day. Orlando questions if it was Dev's lack of knowledge as a Level 7 that gave them away, but Hope explains that their plan failed because she hesitated to kill and so got Dev killed instead. Gabriel, Echo and Hope discuss Hope's mother Charmaine Diyoza, causing Orlando to realize that they tricked him when he learns that Diyoza was a Navy SEAL and thus would've taught Hope how to swim. Before leaving, Orlando promises to bury Dev for Hope with honor.
Some time later, Orlando comes across the three training in the forest. Knowing that Orlando's skills and knowledge as a Level 12 Disciple could be crucial to their plan, Echo tries to make a bet with Orlando to get him to help them out. However, Orlando effortlessly defeats Echo in a fight and loses their bet, resulting in Orlando gaining possession of the cabin back while the others are forced to sleep outside. At some later point, Gabriel brings Orlando some fruit and vegetables as he prays, pointing out using his knowledge as a doctor that Orlando needs it. Orlando warns Gabriel that they won't succeed in their plan because due to what happened with Dev, the Disciples will send more people this time. Orlando knows that they don't have enough people to defeat the group that will come and refuses Gabriel's request to help. Gabriel insists that they don't want to kill Orlando's people, they just want to save theirs. Gabriel tells Orlando that he knows a thing or two about worshipping false gods and that they are both from Earth, brought by a ship to escape the fire that had consumed the planet "largely thanks to people basterdizing the words of their gods." Gabriel challenges Orlando's faith in the Shepherd, pointing out that the Shepherd wouldn't condone what had been done but men would.
After the group returns from another training session, Orlando offers to help them, but states that they don't kill anyone, they get their people and they get out. Echo promises to make "best efforts" to do so, reminding Orlando that as a soldier he knows that in battle they might not have a choice. Orlando interrupts Echo and states that he has 4 years 8 months and 17 days to turn them into Disciples and if they survive they might be ready. Orlando orders them to rest up and they will start at dawn. Over the next nearly five years, Orlando trains the three, ultimately training them to become Level 12 Disciples like himself.
23 hours before the Disciples return for him, Orlando paints Gabriel, Echo and Hope's faces to reflect their new ranks as Level 12 Disciples and tells Hope that Dev would be proud of her as he is. Orlando comments that "the war to end all wars" would be a lot easier if all of his trainees were as determined as the three of them. When Echo comments on how hard it must be to dedicate yourself to something that might never come, Orlando tells them that it wasn't hard for him as he didn't know anything else until he met them. Though he will miss them, Orlando expresses no desire to join them at the dangers of Sanctum, preferring honor and duty instead.
The next night, five Disciples arrive to retrieve Orlando who is tied to a post as part of their plan. The group realize that its a trap too late as Echo detonates a bag of explosive powder, stunning them. As Echo and Gabriel remove the armor from the Disciples, one gets up and tries to stab Echo, forcing Hope to kill him in self-defense to Orlando's distress. Echo reassures Orlando that Hope had no choice and Orlando knows it. Echo notices Orlando's distress every time he sees the face of a Disciple they remove the mask from and realizes that Orlando knows them all, presumably from training them and thus may know a lot more people on the other side. Echo begins killing all of the Disciples, stating that if they leave Orlando alive he will tell the Disciples everything and the Disciples will come after them. Though the original plan was to have Orlando pretend to be their hostage and lead them through the compound, Echo is convinced that Orlando will betray them as while he is their friend, they are not his people. Echo leaves her blade for Orlando to cut himself free and sincerely apologizes to him. Gabriel knows that Orlando will be left alone for years, but departs with Echo and Hope through the Anomaly just before it closes.
On Sanctum, the leader of a group of Disciples sent to capture Clarke Griffin reveals that the Disciples found the graves of the Disciples that Echo killed as well as the corpse of Orlando. Orlando had committed suicide after his friends' betrayal rather than remain alone and left behind a note from which the Disciples had learned of Gabriel, Echo and Hope's five years with him. The group leader offers Clarke Orlando's suicide note as proof of his story, before they enter into a standoff that ends with Raven Reyes killing the Disciples on Sanctum.
In Welcome to Bardo, Gabriel, Hope and Echo, after arriving on Bardo, enact the plan that Orlando helped them come up with. Gabriel notes that in practice, even with Orlando helping them opening doors, it took them 28 out of the 30 minutes they have. Gabriel is still angry about leaving Orlando behind, calling it an unnecessary risk and pointing out that they need an inside man. However, Echo and Hope are banking on Levitt helping them as he had helped Hope and Octavia in the past. Later, Gabriel realizes from Anders' sermon that the Disciples came from Earth through the Anomaly, not Eligius III. As a result, Echo notes that there are things that Orlando didn't tell them.
In The Queen's Gambit, Anders shows Gabriel Orlando's wrapped body in the Anomaly Stone room on Bardo and explains that Orlando had hung himself in the cabin after they left. Having already sent the other bodies off to Nakara, Anders allows Gabriel to say some words over Orlando's body before it is swallowed up by the Anomaly and transported to Nakara. Anders expresses surprise at the amount of information that Orlando failed to share with the group about the Disciples and their religion.
In The Flock, after easily defeating her sparring partner, Hope tells Anders that she was trained by a Level 12 and asks what else he's got. Anders comments that Orlando trained her well which isn't surprising as Anders was Orlando's mentor. Both admit that it was a shame Orlando had to die with Anders calling him one of the Disciples' best.