- —Randy's intro quote, Trails of Cold Steel III
Haha, Don't let that mind. When things come to shove, let your old bro pave the way
- —Randy's intro quote, Zero no Kiseki
A former member of Zemuria's strongest jaeger corps, the "Red Constellation",” Randolph Orlando was second best being the leader's son and the next to inherit leadership. However on one mission that claimed the life of a friend, Randy left the corps not being able to stand the blood-stained tradition of his family. He eventually ended up in Crossbell, where he joined the Crossbell Guardian Force but was discharged due to an altercation with the commander-in-chief.
Immediately following, Randy was scouted to become a member of the Crossbell Police's newest Special Support Section, a place where he finally belonged in facing numerous difficulties alongside Lloyd Bannings, Elie MacDowell, and Tio Plato. He takes the role of the elder brother of the team and watches out for everyone, especially Lloyd in place of Guy Bannings, Lloyd's deceased brother.
After Crossbell's annexation along with Special Support Section's disbandment, Randy continues to pursue Crossbell's independence by assisting preparations with the resistance movement. Despite being reassigned again to the Crossbell Military Defense Force now a subsidiary of the Imperial Army, he decided to head to the Empire after receiving advice from a certain someone. Currently at Thors Academy Reaves II Campus, he becomes the head instructor of Class VIII: Tactics Division.
- Randy is the main power-offense member of the team.
- As of Cold Steel III, Randy is the second Trails character other than Sara Valestein to become school instructor with a jaeger background.