Before November, 2552
|Political and military information|
Roland was a SPARTAN-III commando of the UNSC Naval Intelligence Beta-5 Division. He was a part of the elite Special Operations squad of Headhunters. He, along with Jonah, led a semi-successful stealth attack on an unknown remote moon on which the Covenant were searching for Forerunner relics.
Induction into Headhunters
Roland was inducted into a two-man fire team as part of the special operations program known as "Headhunters". He was paired with Jonah after they were profiled as hitting 97.36 percent of the desired matchmaking criteria. Only one other team scored higher.  Roland maintained an easy-going friendship with Jonah, frequently teasing his teammate over his violent tendencies.
Jonah and Roland were transported to an unknown remote moon in which the Covenant were searching for Forerunner relics. He, along with Jonah, had the mission to destroy six of the total ten Covenant encampments. For this mission Roland was given an experimental active camouflage module for his armor.
In the beginning of the mission, Roland infiltrated the base under cover from his semi-active camouflage to place explosives on four reactors while Jonah engaged the troops in the camp barracks. In this early phase of the mission, Roland placed the explosives successfully, without being spotted. Later on, he helped Jonah on eliminating the remaining targets, all of whom were still confused by Jonah's energy disruptions and flashbang grenades.
Right after Jonah had executed the seemingly last enemies in the base, Roland was impaled with an energy sword by a cloaked Special Operations Sangheili who was wearing a heavily modified Sangheili combat harness. With his last breath, Roland managed to utter "...clear" to Jonah, which meant that the explosives were armed. Jonah detonated them shortly after, vaporizing himself, the cloaked Sangheili, and Roland's corpse.
- Roland's name is likely taken from the Song of Roland, a medieval epic that tells the tragic tale of a courageous Frankish knight of the same name, slain in battle while valiantly facing a vastly-superior force.
- Roland's helmet bore a noticeable resemblance to the MJOLNIR Air Assault helmet.
List of appearances
- Halo: Evolutions - Essential Tales of the Halo Universe
- Headhunters (First appearance)
- ^ To have been in the field during the Human-Covenant War, he must have been a graduate of either Alpha or Beta company, as Gamma was still in training by late 2552.
- ^ Halo: Evolutions - Essential Tales of the Halo Universe, "Headhunters", page 170
- ^ a b Halo: Evolutions - Essential Tales of the Halo Universe, "Headhunters", page 161
- ^ Headhunters, motion comic