Le Paradox's gang was a group of villains led by Cyrille Le Paradox that traveled through time to commit crimes, with the primary goals of proving Le Paradox to be a better thief than the Coopers, and establishing a false line of royalty for Le Paradox. The five lieutenants of the gang also each had secondary objectives that they tried to complete in their own time.
Long before Conner Cooper was killed by the Fiendish Five, he stole the world's largest diamond from a museum. But, the father of a French skunk named Cyrille Le Paradox, members of the Le Paradox clan of thieves, plotted to steal the diamond first and frame Conner Cooper for the crime. Unfortunately for Cyrille's father, he was to slow to act when Conner stole the diamond before him. Cyrille's father was instead arrested and received a life sentence in prison for his crime. His son, Cyrille, now did not have a mentor to teach him thieving, and after a string of failed jobs, he himself got arrested and was thrown in prison.
At some point, following the events of Sly 3: Honor Among Thieves and the release of Cyrille Le Paradox from prison, Cyrille created his own global crime syndicate, where he masterminded thefts of art. Overtime, this made Le Paradox a billionaire and he opened his own museum in Paris to showcase some of the stolen art. However, the skunk had held a grudge against the Cooper Clan because of what happened to his father. Coupled with his own ego of proving himself to be the best thief ever, he masterminded a plan that would get his revenge upon the Coopers and give himself power in society. This plan would leave the Le Paradoxes with the status as the greatest thieves in history and the Coopers with nothing.
Setting his plan into motion
Le Paradox created a plan, where he would time travel to different time periods and steal different Cooper canes, a vital source to their success as thieves. However, instead of doing it himself, Le Paradox hired five different criminals from around the world to assist him in his plan as his trusted lieutenants. These five were: the tiger El Jefe, the armadillo Toothpick, the black bear Grizz, the mouse Penelope and the elephant Miss Decibel. Penelope was an integral part of his plan, since she was a member of the Cooper Gang, and girlfriend of Bentley. Together with Bentley, they had been working on a time machine to see the future of the Cooper Gang. Le Paradox however manipulated Penelope into promises of power and money, coupled with her own growing hatred and jealousy of Sly Cooper. She thought Bentley's continued focus on Sly was holding his potential back and she planned to get rid of Sly, permanently. Le Paradox promised her this help, in return of the plans for the time machine. Penelope stole the plans and built Le Paradox his own time machine, in the shape of a blimp. A key difference between this time machine and the time machine Bentley was building, was that the user did not need an object from a time period, in order to travel to that time period. Instead, the date could simply be inputted. With his time machine complete, Le Paradox transported his lieutenants to their respective time periods, so they could begin their work.
- Cyrille Le Paradox - Founder of the gang who traveled to different time periods as needed, plotting to prove he is the greatest thief in the world by stealing the Cooper canes and establish himself as royalty by forging documents in the past. He was defeated by Sly Cooper and serving a life sentence in prison.
- El Jefe - A mercenary commander. Traveled to Feudal Japan, 1603 AD. Assigned to steal Rioichi Cooper's cane for Le Paradox and dominating Feudal Japan as a dictator. He was defeated by Sly Cooper, returned to the present day and serving his time in a South American prison, rolling cigars without even smoking them.
- Toothpick - A Russian mobster. Traveled to Cotton Mouth Bluff, 1884 AD. Assigned to steal Tennessee "Kid" Cooper's cane and form a plan to rob the gold from Cotton Mouth Bluff to become a billionaire in the present day. He was defeated by Sly Cooper, but never returned to the present at all. He was arrested and sentenced to work on the railroads in a chain gang instead, but unknowingly stepped in the path of moving train, which he could not hear, due to being deafened by Sly using his train whistles against him, and he was ran over ever since.
- Grizz - A gangster/graffiti artist. Traveled to Gungathal Valley, 10,000 BC. Assigned to steal Bob Cooper's cane, operating his scheme to forge art in the past and hide it, only to dig it up in the present day to become rich and famous. He was defeated by Murray, returned the present day, and serving a lengthy prison sentence, where he then became a rapper and paint portraits of his fellow inmates.
- Penelope (Black Knight) - An inventor, former Cooper Gang member, and Bentley's girlfriend. Traveled to Medieval England, 1301 AD. Assigned to steal Sir Galleth Cooper's cane after she left the Cooper Gang because she was desired to use Le Paradox's resources to eliminate Sly Cooper, so she and Bentley could become billionaires by making weapons for the highest bidder. She was defeated by Bentley, returned to the present day, and sent to Europe's highest-security prison. She quickly escaped, and sent Bentley mysterious postcards with her symbol spray-painted on the photographed locations.
- Miss Decibel - A British musician and hypnotist. Traveled to Ancient Arabia, 1001 AD. Assigned to steal Salim al-Kupar's cane and forge documents to establish a fake royal ancestry line for Le Paradox to use in the Present day. She even wanted to do Le Paradox's bidding, so she could earn his love. Unfortunately, Le Paradox promptly betrayed and left Miss Decibel in Arabia, after she was defeated by Sly Cooper. She was brought back to the present and incarcerated. After that, Miss Decibel had her trumpet removed from her trunk, then she enrolled in anger management classes and began a music class in the prison. With continued good behavior, Miss Decibel may be eligible for early parole.
- Le Paradox's museum, Paris, Present day
- El Jefe's fortress, Japanese village, 1603 AD
- Saloon, Cotton Mouth Bluff, 1884 AD
- Grizz's fortress, Gungathal Valley, 10,000 BC
- Black Knight's castle, English town, 1301 AD
- Miss Decibel's palace, Arabian city, 1001 AD
- Le Paradox's blimp (mobile headquarters)
Each member of Le Paradox's gang employed a number of guards to protect and patrol around their various facilities:
- El Jefe
- Miss Decibel
- Cyrille Le Paradox
- There were originally going to be several more lieutenants, including a mole and an alligator, but they were somehow scratched off.
- This is the only group of major villains where all of the members are mammals.
- This gang is known as "Le Paradox's Gang" due to the fact that it has no official name, unlike all other villainous organizations in the series.