At some point after the Cordyceps brain infection outbreak, Robert became a prominent arms dealer and leader of a group of smugglers in the Boston area. His group also dealt in smuggling other contraband such as pills.
Events of The Last of Us
Robert was an arms dealer who was supposed to sell guns to Joel and Tess. Instead, he sold the guns to the Fireflies. In fear, he sent two men to kill Tess, but to no avail. As shown in the Boston Q.Z. map, he used to live in Area 2 of the zone but changed location in order to hide from Joel and Tess. He also made deals with the military, usually bribing them with a portion of the supplies he gathered so he could keep trading.
In retaliation, Tess and Joel decided to go after him. They managed to infiltrate Robert's warehouse in Area 5, where Robert had several men ready to protect him. After dealing with the hired protection, they finally caught up to him. Robert tried to fend them off with a 9mm pistol but quickly ran out of bullets, forcing him to flee. Joel and Tess pursued and caught up to him. Robert attempted to flee once more but was knocked down. The duo questioned him, but Robert was hesitant to explain himself. After being beaten and having his arm broken by Joel, Robert revealed that he sold the guns to the Fireflies. Desperate, he suggested they take the weapons by force. Tess commented on how stupid his idea was and executed him with a gunshot to the head.
Robert was an extremely conceited, yet cowardly person. He attempted to have Tess killed after he refused to give her the weapons she and Joel had paid for (which one can assume led to their anger against him). Even in defeat, Robert was quite arrogant, as shown when he refused to tell Tess what happened to their guns. Robert comes off as a coward as he tried several times to negotiate his way out of Joel and Tess' interrogation, even suggesting that the group take on the Fireflies head on (a completely absurd suggestion, considering how heavily armed and experienced the group is).
He was also disliked by the other members of his gang, as he had not paid them in quite some time. Many of his men regretted and disliked their jobs as his bodyguards, and insulted him behind his back. Robert also garnered dislike from creating counterfeit ration cards as payment, as discussed between Tess and Joel when they were going to see him. Joel summarizes that "You can leave it to [Robert] to piss everyone off."
- Despite his short screen-time, Robert is indirectly responsible for the events of the game. He owed weapons to Joel and Tess, yet he gave the weapons to Marlene, who Joel and Tess had to work for in order to take back their weapons, thus leading to Joel and Ellie's long journey.
- Ironically, Robert's last plea to fight the Fireflies, which Joel and Tess dismissed, was later carried out by Joel to save Ellie's life in "The Firefly Lab".