Roosevelt was born in the former state of Oklahoma, home to the largest concentration of agricultural land in the post-War USA. Adopted by his parents when he was little more than a baby, Roosevelt grew up helping out around the family's sprawling bighorner ranch - home to a close-knit community of farmhands, who introduced Roosevelt to Oklahoma's wider landscape of ranchers, merchants, and post-apocalyptic cowboys. Outgoing and precocious, with a silver-tongued approach to both business and pleasure, Roosevelt was a welcome sight for many a weary traveler passing through the American midwest.
During this time the Plains Commonwealth had been plagued by Caesar's Legion, an imperialistic dictatorship seeking control of the southern states, who infrequently staged brutal reprisals against uncooperative landowners. One night, whilst its occupants slept, legionaries from the Red Okie Centura crept onto the ranch, and set fire to the buildings and surrounding land. The entire farm burned to the ground overnight, along with close to a hundred bighorners and other assorted livestock species. Those that weren't killed by the fire outright were snapped up by the Legion, to be used as soldiers, slaves, or worse. Roosevelt and a handful of farmhands managed to escape by running across the burning fields, but he lost both parents in the attack.
With no family left to him and no home to return to, a devastated Roosevelt found work as a mail courier on the west coast, running letters and packages for the Mojave Express. The work was difficult, long hours for what amounted to little pay, but the lack of real responsibility suited Roosevelt just fine, and for several years he was free to charm his way across middle America, leaving a string of broken hearts in his wake. During this time he was a frequent visitor to the towns of Hopeville and Ashton on the Californian border, one of a handful of Couriers willing to run packages to the fledgling community.
It was on one such delivery run between southern California and the New Vegas strip that Roosevelt was ambushed by a group of Great Khans just outside of Goodsprings. Led by their mysterious, smooth-talking commander, the Khans relieved Roosevelt of his personal effects, before shooting him in the head and dumping his body in an unmarked grave. He was subsequently found and nursed back to health by the people of Goodsprings.
Since then, Roosevelt has been tracing his attackers' next steps with the intention of recovering his belongings. Not the package itself, for which he frankly couldn't care less, but the items that were on his person when the Great Khans robbed him: the remains of his mother's wedding ring, its metal warped by the flames; a bighorner tooth strung on a loop of wire; and a leather cord bracelet given to him by his father. These seemingly useless items were some of the last reminders of Roosevelt's home, and he'd give anything to retrieve them.
Roosevelt's search would eventually bring him to the neon-soaked streets of New Vegas, where the leader of the Chairmen, Benny, was busy planning to "liberate" the city using the same package he had stolen from Roosevelt the night he left him for dead. From Benny, Roosevelt learned that his belongings had been bartered away soon after his murder, and were now in the possession of members of the wasteland's three warring factions: the NCR military, the Great Khans, and the Legion at Cottonwood Cove. Roosevelt subsequently reclaimed the package Benny had initially stolen and left New Vegas, little realizing that he was now in possession of the key to Mr House's empire: a data storage device containing the activation codes to the city's missile defense system.
Roosevelt's headshot. Note the scar tissue on his left temple - a lingering reminder of Benny's attack.
A note on Ships: Roosevelt had stars in his eyes when he first saw Alex (literally: Alex was leaning over him checking him for a concussion at the time) and he's had stars in his eyes every single time he's looked at him after that. It's not easy, between Alex's schedule and Roosevelt's determination to punish himself, but somehow Alex manages to pin his flighty boy down. Sometimes. Roosevelt has a very obvious crush on Col. James Hsu of the NCR's Camp McCarran, which Hsu seems to find more amusing than anything else. Despite being two gay men living in close proximity, Roosevelt/Arcade are like... the opposite of a ship. They get along fine, but there's a less-than-zero amount of attraction there. Roosevelt has a little bit of a thing for Boone, though, who is the Straight Man in every sense of the word - Boone has dragged Roosevelt's drunk ass home too many times for Roosevelt not to be pathetically in love with him.