Roundabout is a man of Asian ancestry, with short cut black hair that is graying at the temples. He wears round glasses, a suit, and a bow tie.
He seems to be very proper in his speaking, as seen when he is talking to Professor Malestrom. Like his namesake, "Roundabout" speaks in a roundabout way with people, making sure to imply something without saying it, and covertly having people tell him what he wants to hear.
Such was the case with a British Intelligence worker, as Roundabout had informed his department to be on alert for any suspicious or illegal criminal activity in Botswana. He is able to effortlessly present or come across as a pleasant man, congratulating the employee who warned him, while still conveying his true loyalty to V.I.L.E. in a moment's change.
He is a man of elite education and standing, having both the intelligence and foresight to maneuver parties within British Intelligence to give him information to monitor possible actions against V.I.L.E. from afar. Due to this, while not physically present for Faculty votes or discussions, he still shows interest in holding the position now empty by Shadowsan's betrayal.
Roundabout is a V.I.L.E. agent and now Faculty instructor who had infiltrated Her Majesty's secret service. He frequently used his position to pull strings and get any captured operatives released from custody, and was running an illegal diamond mining operation in Botswana.
Unlike all the other candidates, he didn't participate in his operation hands-on, due to his "day job", and due to receiving advance notice of the police finding out, he was smart enough to close shop before A.C.M.E. could bust it wide open. These factors were what convinced the other Faculty members that he was the ideal choice to succeed Shadowsan as their fifth member.
He later used his connections to covertly have V.I.L.E. Academy moved to a new location in an abandoned castle in the Outer Hebrides of Scotland. He primarily communicates with his fellow Faculty members by video chat, due to his position at MI6.
In the episode "The Jolly Good Show Caper", he, along with V.I.L.E. agents El Topo, Le Chevre, and The Troll, planned to capture Carmen by staging a fake heist of the Crown Jewels, knowing Carmen would steal them herself to keep them out of V.I.L.E.'s hands.
When Carmen attempted to do so, The Troll hacked into Player's computer systems and set off the alarms, causing Carmen to be caught, and taken by the police, whereupon Roundabout would pull strings to get her out and have the Cleaners bring her back to V.I.L.E. Academy. Roundabout then entered the tower to supposedly conduct forensics on the scene, but with the help of the Troll, he stole the crown himself, replacing it with a fake, and handed it off to Le Chevre at Big Ben. Shadowsan caught up with him and the two engaged in a duel, whereupon the police arrived at the scene, but to Roundabout's surprise, they were there to arrest him.
Shadowsan explained that Carmen had been onto his plan from the start, knowing he'd concoct an elaborate scheme, and so they planned around that to make it seem like he'd won. The two policemen driving the paddy wagon Carmen had been put into had been Zack and Ivy in disguise, and Player hacked into the Troll's computer systems to prevent him from finding Carmen, he also recorded Roundabout's theft and broadcasted it to ACME. Carmen, in disguise, swiped the crown from Le Chevre and deposited it in Roundabout's office, to be discovered by Agent Zari and Chase Devineaux. Roundabout was promptly arrested, however, The Cleaners extricated him from police custody to bring him back to the rest of the Faculty. What they plan to do to him for his failure is unknown, if they even plan on punishing him at all.
As one of the five masterminds of V.I.L.E., Roundabout has near supreme authority in the organization, and with his former position in British Intelligence, he was perhaps Carmen's most formidable adversary. As a high position agent of MI6, Roundabout was able to access and monitor information not easily accessible to others.
He made use of his position to gain intelligence on when authorities arrive and keep track of both V.I.L.E. and A.C.M.E. movements and coordinate V.I.L.E. operatives to stay one step ahead of A.C.M.E. upon learning of Carmen's "alliance" with them.
Appropriately for someone filling the position held by Shadowsan and Dexter Wolfe, he too is a master of stealth, but his stealth expertise is by avoiding detection through diversionary tactics. Diverting attention away from himself rather than avoiding it altogether.
In combat, Roundabout is shown to be a highly capable fencer, claiming he was previously the captain of the Oxford fencing team and was skilled enough to overwhelm Shadowsan, a skilled swordsman in his own right.
- His name is a play on a British roundabout, a road junction at which traffic moves in one direction around a central island to reach one of the roads converging on it.
- His codename might also be like the idiom, such as to say something in "a roundabout way" to imply something without saying it. As a spy, he would need this social skill in intelligence gathering and coercion.