"Tings change, One-Eye. And so will de color of your fur when I run ya through!"
Not much is known about Red Rum Roger's past other than once being on the run from the law enforcement of his era around the time he had met Henriette "One-Eye" Cooper. Having crashed his original ship, the Wandering Trident, into a harbor in Jamaica, his island home, he encountered Henriette, who he tried to steal her ship from. Upon being bested in combat, Red Rum Roger decided to join her, and so, the two pirates became a duo, and eventually gained more allies. Together, they helped form Henriette's crew, and Red Rum Roger became Henriette's first mate.
However, upon the arrival of "Black Beard", Roger's loyalty to Henriette would be put to the test, a test that Roger would fail shortly afterward by selling Henriette out to the authorities. This would pave the way for a hidden alliance between Roger and Black Beard, one that not even Henriette would know about.
When the Cooper Gang arrived in the Age of Pirates after their scuffle with Le Dude in Celtic Scotland, Red Rum Roger was there to greet them. He told the gang that Henriette was being held somewhere in a cavern not far from their safehouse. He even helped the Cooper Gang during a recon mission, gaining their trust. But when the gang released Henriette, Roger made an attempt to kill everyone at once. Henriette defeated him in combat, however, and Roger quickly evaded capture, fleeing to his boss and leaving one of his swords behind. This sword would later be used for Sly's Buccaneer Costume.
Roger attempted to intercept the Cooper Gang when they were heading to the ship graveyard to get an ancient sword for the main assault against Black Beard, but Carmelita's Shock Pistol shot down Roger's vehicle, forcing him to retreat back to Black Beard once again.
Eventually, during the final battle between Black Beard and the Cooper Gang (specifically Murray), Red Rum Roger decided to join the battle, attacking Murray in the foreground while the real foe, Black Beard, fired from the background. After a long and tiring battle, Roger was flung into one of the Emerald Eclipse's cannons, and fired at Black Beard as Penelope ejected herself out of the mech.
It is later revealed at the end during the credits that the authorities found and imprisoned Roger. It isn't known what happened to him after that, but word spread amongst other pirates that he had been hung.
Red Rum Roger is a specifically a Short-tailed Albatross, and as such, he has a yellow head and white feathers. He also has a full head of black dreadlocks, which he covers with a pirate hat with Penelope's logo on it (This logo is covered up by a patch to deceive the Cooper Gang into thinking his hat was merely damaged). When he worked with Henriette, he wore an old, worn out blue coat that had a patch of the British Flag attached to the left sleeve, implying that either he stole this coat from someone working for the British Navy, or that he possibly used to work for it himself, wearing the patch as a form of patriotism. Upon being recruited by Penelope to act as her personal assistant while in the Age of Pirates, he wears a dark orange tuxedo with Penelope's logo attached to the left sleeve. In both outfits, he wields two sabers, one of which is abandoned, leaving him with only one, which he wields with his left hand.
Red Rum Roger is notoriously opportunistic and power-hungry; if there is money to be had, or if there is power to gain, he won't rest until he obtains it, but only if he's given the chance. Roger is also rather serious as a result of his old status as Henriette's first mate, making him intimidating to other pirates, specifically those who know him already, who fear him mainly due to the rumors spread about him. This fact is often abused by Roger to keep his fellow pirates in line. However, he'll panic if something goes wrong, as he often has trouble improvising.
Red Rum Roger's swordsman skills, while being incredible, pales in comparison to Henriette, but not enough to negate the danger him holding a blade poses. He commands his fellow pirates effectively as well. His main weakness, however, is his poor skill at sailing; he has crashed more ships than anyone Henriette has ever known, and is never allowed to actually steer ships, lest they crash into harbors or rocks. In combat, thanks to Penelope's enhancements, he is capable of using ice and water to aid in attacking his foes, such as freezing the arena he and Murray are fighting in to make it hard to walk on, or to summon highly-pressurized, geyser-like water to boil Murray alive.
- Defeating Roger the first time gives the player the "Rats With Wings" Trophy.
- If the player manage to defeat him when facing Black Beard, the game will reward the player the "Nice Landing" Trophy.
- Besides Penelope herself, Red Rum Roger is the only character whose species isn't native to the Caribbean. Even the flashlight guards, the Putrid Pelicans, are based on pelicans native to the islands.