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Sly was born into the lineage of the Coopers under the tutelage of his father Conner Cooper. Between the jobs that his father's gang would pull off, Sly would spend time with Jim McSweeney, a member of the gang and Conner's friend. At the age of three, Sly was taken by his father to a museum on the Ligurian coast in Italy where they met up with McSweeney, who then took the map to the Cooper Vault—an island-wide safe that holds the riches of the entire Cooper Clan—and hid it in the museum.
As Sly grew up, he learned about his family's history as master thieves. At the age of eight, he was to follow in their footsteps and inherit their legacy, a book called the Thievius Raccoonus. On the night Sly was to inherit the book, a mysterious gang of criminals known as the Fiendish Five infiltrated the Cooper home. Try as he might, Conner failed to defend himself, his wife and his son from the gang, resulting in the death of both parents. The Fiendish Five ransacked the house in search of the Thievius Raccoonus as Sly watched helplessly from the closet. Once the villains found the book, they tore it into five parts before leaving. Sly, now an orphan, was placed in an orphanage, where he met his now lifelong friends Bentley and Murray. With their encouragement, Sly was determined to live up to his namesake as an accomplished thief.
The Orphanage
As children, the trio planned to steal the orphanage's cookie jar from Mrs. Puffin, the director of the orphanage, who kept the children's holiday cookies for herself. This desire came from the fact that "she was so nasty" and that Murray would spend sleepless nights thinking about the cookies. They started to strategize and gave themselves a name; the Coopers 3.
After much plotting, Bentley had come up with the perfect plan: Sly would hide in Puffin's trash bin until after she had left for the night and would swipe the cookies then. According to his calculations, Bentley decided they had only five minutes between Puffin's departure and the janitor's arrival. Unfortunately, Sly had misinterpreted Bentley's instructions and was nearly caught by the janitor. Due to Murray's quick thinking, Sly was yanked through the window at the last second before the janitor entered the office. However, the mission was not a failure, as Sly had stashed the cookies in his hat at the last moment. After their first successful heist, the Cooper Gang was born.
Meeting Carmelita
Many years later, Sly arrived in Paris "looking for a little adventure" when he came across the Paris Opera House. While comparing stories with INTERPOL Inspector Carmelita Fox sometime later, the accounts differ, so the exact details are impossible to know. Sly claimed he was just there to "soak in the architecture" while Carmelita stated that he was there to "case the joint." In the end, Sly helped catch a rival thief, the stage manager Pierre, which benefited Carmelita and started the two's relationship.
Sometime later, Sly stole an item known as the Fire Stone of India, which put Carmelita after him again. He planned to give it to Carmelita as a token of his feelings for her.
Sly Cooper and the Thievius Raccoonus
Ten years after the Fiendish Five stole the Thievius Raccoonus, Sly had garnered a worldwide reputation as a cunning thief. He and the gang embarked on a quest to steal back his inheritance and avenge his parents' deaths. Starting in Paris, Sly stole a police file from Inspector Fox's office, which engaged her interests, though she was unsuccessful in apprehending Sly at the scene. The file contained all of Carmelita's data on Sly and his background, as well as the Fiendish Five. Ready to finally become a master thief like his ancestors, Sly and the gang began a pursuit that would ultimately change their lives.
As the gang traveled around the world, they confronted each Fiendish Five member in their respective hideouts, defeating them one by one and collecting the pieces of the Thievius Raccoonus that they had taken. He used them to learn the techniques of his family.
After the defeat of the Panda King, the gang headed to the Krakarov Volcano in Russia. Bentley had analyzed several unique vehicles that the other members of the Fiendish Five had at their bases of operation, the alloy of which could have only come from this volcano. On the journey, Sly examined the pages of the Thievius Raccoonus. Several of its pictures depicted a shadowy owl-like figure in the background. He compared these images to the little information that Carmelita's police file contained on the leader of the Fiendish Five, Clockwerk. He found that they matched his silhouette, leaving him to wonder if this was a simple coincidence or something more.
Arriving in Russia, the gang was attacked almost immediately by a powerful death ray. With the latest modifications of the Cooper Van, Sly was able to fight off the robo-falcons that swarmed around them while they dodged the death ray. Inside the base, Sly found that Carmelita had been captured and placed in a chamber. Despite Bentley's warnings that this was a possible trap set up by Clockwerk, Sly will not willing to stand by and let Carmelita face immortal doom.
After sneaking across the heavily secured room, he arrived at the chamber, but the door closed behind him as soon as he stepped inside. Upon seeing Sly, Carmelita began to think that he was the culprit behind her capture, but Sly assured her that it was a rescue. Shortly after, Sly lost consciousness from the toxic fumes that filled the room, while Clockwerk appeared on the computer screens and chided Sly's sentimentality. Bentley sprang into action and hacked Clockwerk's security, turning off the gas just before Sly's brain could be "turned to cheese."
Once Sly regained consciousness, Carmelita apologized to him for her accusations and promised to make it up to him if he could free her. After escaping Clockwerk's clutches, the two briefly reasoned with each other how, at the moment, they were both on the same side and Clockwerk was the enemy, to which Carmelita agreed. Therefore, she called a temporary truce with Sly in order to work together to bring down Clockwerk. However, she reminded Sly that when this was all over, she would go after him as well, after a ten-second head start. Carmelita offered Sly the use of her jetpack, which he had to acquire at the top of the death ray. Upon reaching the top of the tower, which had subsequently sunken into the lava, he equipped the jetpack shortly before Clockwerk revealed himself. The owl explained how he kept himself alive through a steady diet of jealousy and hate for the Cooper line, awaiting the day he would finally eclipse their thieving reputation.
Those words confirmed Sly's suspicions as to the identity of the figure in the pictures within the Thievius Raccoonus. Before engaging in battle with the owl, Sly inquired about his reasoning for sparing his life when he attacked his home. Clockwerk simply stated that he wanted to show the world that without the Thievius Raccoonus, the Cooper line was nothing, something that Sly disagreed with, stating that the Thievius Raccoonus was a book created by master thieves and not a book that "creates" master thieves. The two then engaged in battle, and with Carmelita's help, Sly was able to shoot down the owl. After Clockwerk dropped down into the lava and began his auto-reconstruct sequence, Sly seized control of the jetpack and made his way to the Clockwerk's head, by foot, to destroy it. As Sly made continuous blows at Clockwerk's head, the owl said his final words: "Cooper, you will never be rid of me! Clockwerk is superior!"
With the entire Fiendish Five defeated, Sly expressed his pride in managing to recover his family heirloom. He acknowledged the help he had from Bentley and Murray, who stuck with him through it all, even though it was not easy for them. Commenting on both of their abilities, he realized how lucky he was to have friends like them, and could never ask for better ones.
With Clockwerk out of the picture, Sly and Carmelita were back to playing cops and robbers. She confronted Sly along a catwalk, ready to bust him. However, she remained true to her word and gave him the ten-second head start, which he used to stare her down. At the last moment, Sly kissed her. Dazed by the sudden romantic advance, Carmelita failed to realize that Sly used the distraction to handcuff her to the railing, which enraged her. Sly was certain, however, she would be chasing after him again very soon. Shortly after Clockwerk's defeat, Sly restored the Thievius Raccoonus to its original state (if all the pages are found) and felt that he had truly earned the title of "master thief".
The Adventures of Sly Cooper, Issue 1 / To Catch a Thief
Sometime after restoring the Thievius Raccoonus, while trying to steal the Mona Lizard by Leo Rhino, Sly came across an invitation to a wedding in Monaco between Dimitri Lousteau, a nightclub owner, and Madame D'Oinkeau. Unable to pass up the chance to steal D'Oinkeau's gift to Dimitri, the Venus de Whalo, the gang headed to Monaco. With everyone downstairs, including Carmelita (who was invited by D'Oinkeau to protect all of Dimitri's art), Sly entered the manor through the attic via skylight. He unwittingly discovered a forgery operation by Dimitri, but easily dispatched the guards as they try to attack him. However, security closed in and seemingly captured him. Several security guards headed downstairs and alerted Carmelita to the situation, who jumped at the chance of arresting Sly Cooper. Dimitri tried to keep Carmelita from heading upstairs, but was unable to stop her, and so left to "get some ice."
Arriving in the attic, it is revealed to Carmelita and D'Oinkeau that Dimitri is an art forger and that Sly Cooper was not apprehended. Realizing that the security guards were the Cooper Gang in disguise, Carmelita charged back downstairs but was too late to stop them from escaping with the Venus de Whalo in tow. Outside, still in costume, the gang stuffed the statue into the van. Bentley revealed that, despite their success, they are twelve minutes over schedule and the next and the final ferry out of Monaco wouldn't leave for another 45 minutes. Sly took the opportunity to stall Carmelita while Bentley wondered if Sly purposely put them over schedule just so he could mess with her.
On his way to where he knew Carmelita would be, Sly reminisced about the gang's first job, the "Cookie-Steelin' Plan." Carmelita traced the Cooper van's tracks outside of the mansion, wondering out loud what kind of an asset Sly would be if he worked for the police. Sly dropped down from above and asked where the fun in that would be. Before she could shoot him, he knocked the shock pistol out of Carmelita's hand and pointed out that he only steals from criminals. Carmelita retaliated with the fact that the criminals he steals from take from the common man, so by stealing from them Sly is perpetuating the cycle. They both think to themselves that the other is obsessed with them. Sly begs to differ, and uses their first meeting as an example of his good intentions. The two of them tell the story of how they met, with minor differences. At the end of it, while Carmelita doesn't admit to Sly's goodwill, she states that she is no longer the rookie of that time.
As they were telling the story, Carmelita had been inching closer to where her shock pistol lay, and Sly gives her permission to go for it, pointing out that he has nowhere to go on the bridge, as he can't swim. She dove for the gun and said that Sly will be in handcuffs along with Dimitri. However, while she was looking away, Sly jumped off the bridge. Afraid that he would drown, Carmelita rushes to the edge and looks over, where it is revealed that he had landed on the last ferry out of Monaco with his gang. Carmelita yelled out that she'll get him if it was the last thing she did, and Sly thinks to himself that his father would have liked her.
Sly 2: Band of Thieves
Two years after Clockwerk's defeat, Sly and the gang discovered that the untarnished parts of the owl had been salvaged from the Krakarov Volcano and were being held in the Museum of Natural History in Cairo, Egypt, where they were to be restored in the "Clockwerk Restoration Project." With the help of Bentley and Murray, Sly broke into the museum in order to steal the parts so they could be properly destroyed once and for all. As Sly entered the Clockwerk exhibit, he discovered that the parts were already gone. Carmelita and her new partner Constable Neyla, hiding in a pair of sarcophagi, revealed themselves. While Carmelita was sure that Sly was thief responsible, as he had the motive, and crooks "always return to the scene of the crime." However, Neyla was not so sure Sly was the culprit, as she let slip that the guard casualties and method of entry pointed to it being a Klaww Gang job. As Carmelita reprimanded Neyla, stating that she only allowed her to be apart of this case as a favor to the Contessa, Sly and his gang escaped the museum.
It did not take long for the gang to discover the location of the Clockwerk tail feathers. They tracked them down in Paris, where Dimitri, the forger previously met in Monaco, was using them (due to their indestructible alloy) to constantly print counterfeit money. Over the course of the night with help from Neyla, who let it be known that she purposely tipped Sly off to the Klaww Gang, the gang destroyed Dimitri's operation and left France with the tail feathers. They spent some time in Monaco before heading off to the next location: a palace in India owned by another Klaww Gang member, Rajan.
Sly crashed a party being held at Rajan's palace while in disguise, dancing with Carmelita (who was undercover along with Neyla and the Contessa) to distract the crowd while Murray cut the Clockwerk wings free from a large statue. After Carmelita discovered that the one she was dancing with was Sly, she broke cover and started making arrests left and right. Rajan retreated to his spice temple while the gang headed to Bollywood. During their small vacation, they learned that Rajan also had the Clockwerk heart, which he was using as a pump to water his spice plants. Eventually, the gang got their hands on one half of the heart, but were betrayed by Neyla while attempting to collect the other half. Sly, Murray and Carmelita, who Neyla claimed was allied with the Cooper gang, were all arrested and imprisoned in the Contessa's Prague-based rehabilitation clinic while Bentley escaped.
Sly was thrown into "the hole": a chamber that was used to break criminals' minds with days of isolation. Bentley, working on his own, eventually broke Sly out. He also discovered that the Contessa was a secret member of the Klaww Gang that used her powers of hypnosis to reveal the location of criminals' fortunes. The two set to work on freeing Murray, who was being held in the prison area of the clinic. After freeing him, the Contessa escaped on her blimp to her castle estate, and the gang celebrated their breakout. After a relatively long break, the gang followed the Contessa to her castle, where she was being attacked by Neyla, who had now betrayed her, and her army of mercenaries. Carmelita was being held in the Contessa's "re-education tower" where she was being bombarded by the hypnotic effects of the Clockwerk eyes. Against Bentley's advice, Sly freed Carmelita while collecting the Clockwerk eyes, before defeating the Contessa. Now a fugitive from the law, Carmelita accepted Sly's help in escaping from Neyla.
Now fully committed to taking down the spice empire, the gang headed to Canada where Jean Bison, the Klaww Gang's chief of transport, was located. They discovered that he was in possession of the Clockwerk stomach and both lungs, which he was using to run his three "Iron Horses": trains that carried spice all across North America. After three successful train heists, Sly decided that he needed to help clear Carmelita's name without turning himself in. Following the robbery of his trains' power sources, Bison headed to his lumber camp where he was holding a series of challenges called the "Lumberjack Games," with the Clockwerk talons as the prize. Realizing that Bison had the judges so scared as to always give him perfect 10s in score, the gang took out all of the judges and replaced them. Giving him all zeroes, Bison caught on to the trick and captured the gang. They defeated him inside the prison where they were held, before escaping. Realizing that Bison had taken all of their Clockwerk parts and sold them to Arpeggio, the gang rushed to the northern lights battery before Arpeggio's blimp could pick it up.
As soon as the battery was hooked into the blimp, Sly headed to the smaller balloon that was holding all of the Clockwerk parts. It was there that he learned that Neyla and Arpeggio were conspiring the entire time to collect the robotic bird for themselves. In an impassioned attempt to stop the construction, Sly accidentally locked the parts into place. Neyla and Arpeggio confronted him, and Arpeggio revealed his master plan of using the northern lights (which were stored in the northern lights battery) to hypnotize everyone below the blimp into a fit of rage. As rage is what kept Clockwerk alive for centuries, Arpeggio was planning to use this hate to remain immortal inside of Clockwerk for eternity. However, before he could enter the Clockwerk frame, Neyla attacked him and entered for herself, becoming "Clock-La." She then killed Arpeggio and escaped the blimp, preparing to absorb the hatred that would come as soon as the blimp passed over Paris. Sly, along with Bentley and Murray, toiled to dismantle critical parts of the blimp before finally sending out a signal to Carmelita, who arrived shortly after in a police helicopter.
Carmelita agreed to join forces with Sly in order to defeat Clock-La. Jumping into her helicopter, Sly took control of its gun and attacked her. Before she could be defeated, however, she located and captured Bentley and Murray within the battery, destroying the blimp in the process. Sly glided to Clock-La and attacked her head, forcing her to the ground. As she crashed to the ground, Bentley recalled that Neyla mentioned a "Hate Chip." While trying to remove it from the frame, Bentley was crushed by the beak and paralyzed from the waist down. With the Hate Chip removed, Clockwerk's body exploded. Despite this, none of the individual pieces were damaged. Carmelita, having just arrived and being angry at not being able to attack Neyla herself, stomped on the Hate Chip, which caused all of the parts to disintegrate on the spot.
Sly and his family were finally free from the menace of Clockwerk. In spite of this, Carmelita needed to uphold the law and put the gang, Bentley included, under arrest. Realizing that his gang was in no shape for a quick getaway, Sly promised to surrender with no trouble if Carmelita let Murray walk with Bentley in his arms. She agreed, and was soon after given a reinstatement and promotion by her boss, Inspector James Barkley. While on the short helicopter ride across town, Carmelita quickly loosened up and the two shared stories about their interests. Some time later, she realized that the "short ride" had already taken two hours. While she checked on the pilot (who was gone, thanks to Murray), Sly picked his handcuffs and escaped with his paraglider. As he flew off, Carmelita swore that she'd get him and quietly remarked that she'd see him again soon.
The Adventures of Sly Cooper, Issue 2
After receiving a messenger pigeon, Sly headed to Heathrow Penitentiary to meet Jim McSweeney. He sneaked into the prison and found McSweeney's cell and, after passing a test to prove his identity, learned the location of map to Kaine Island where the Cooper Vault was located.
After trying and failing to get the map from a museum in Italy, Sly and Murray realized that they would need Bentley, who was currently in the hospital after the accident at the end of their last adventure. While they broke him out, Carmelita took over the investigation of the failed museum heist. She retrieved the painting that Sly had touched and took it to her apartment. Sly, planning for this, broke into her apartment and stole the map, which had been hidden underneath the canvas.
After escaping from the scene, Sly met back up with Bentley, who had made modifications to a wheelchair to suit his needs. As the two talked about the upcoming heist, Murray entered the safe house and told them that he was leaving the gang so that nothing like Bentley's accident would ever happen again. Despite having just lost one third of their team, Sly and Bentley headed out for Kaine Island. When they arrived however, they saw that the island had been transformed into a fortress by a mandrill scientist named Dr. M. With security "as tight as Fort Knox," Sly realized that it would take a team of specialists to be able to sneak onto the island and reach the Cooper Vault.
Sly 3: Honor Among Thieves
They set out for Venice directly to re-recruit Murray, who had been seen in the area. With the help of Dimitri (who had been imprisoned there), Sly found Murray, who promised to rejoin the gang after making the "black water [run] pure" as part of his Aboriginal dreamtime training. The "black water" was the pollution of the canals around the city, caused by the crime lord Don Octavio in an attempt to lure in an "audience" for his opera. Sly and Bentley, with Murray's help, foiled the plans of the Don and, with his Guru's request fulfilled, Murray rejoined the gang.
Despite this, Murray felt bad for never returning to the Guru, so to find closure the gang headed to Australia. However, miners in the area had since destroyed the surrounding land while searching for opals, and had inadvertently released the Mask of Dark Earth, an ancient cursed mask that the Guru was tasked with keeping dormant. Though the mask did escape its confines, the gang destroyed it (with Carmelita's mercenaries' help) and the Guru agreed to join the gang, becoming the first new member since the gang's creation.
As Bentley's RC skills were not sufficient for the heist, the gang went looking for a specialist. They found one in Penelope, a mouse from Holland and the crush of Bentley, but before she would join, the gang needed to prove their worth by beating her boss, the Black Baron, in aerial combat during the ACES competition. It is revealed, after his defeat by Sly, that the Black Baron was Penelope in disguise. She joined the gang and took a liking to Sly, despite him being completely oblivious to her crush.
Despite Sly's reservations, Bentley assured him that the next member to be recruited must be one with supreme demolition skills. It was decided that the gang would head to China to recruit the Panda King. He was found in a deep meditative trance, which he was snapped out of thanks to Sly and the Guru. He had been meditating after his daughter, Jing King, had been kidnapped by General Tsao, who was forcing her into marriage with him. Along with the arrival and help of Carmelita, Tsao was arrested and Jing was saved. The Panda King and Sly both put aside their differences and the team gained another member.
Finally, after a call for a favor from Dimitri (which Sly owed him after he gave Sly the location of the Black Baron's flight roster back in Holland), the gang headed to Blood Bath Bay to help him retrieve his grandfather's diving gear. However while retrieving the gear, Penelope was kidnapped by pirate captain LeFwee. The rescue attempt, despite its hitches, ended with LeFwee falling into shark-infested waters and Penelope rescuing Bentley. She then realized that she was attracted to Bentley for his smarts, despite Sly's athletic ability.
The Cooper Gang sailed their newly acquired pirate ship to Kaine Island for the heist. Sly made it up to the vault's door, but Dr. M interfered. In a fight with Dr. M's mutant primate Sly both lost his cane and was severely injured. Carmelita arrived just in time and battled the mutant, saving Sly.
Sly recovered from his injuries and, after battling Dr. M's mutant Whale-Fly, entered the vault with Bentley and Murray. As the vault was meant for Coopers only, Sly continued alone while Bentley and Murray guarded the entrance. Sly overcame many challenges based on the Cooper family's thieving abilities, with each test built by one of Sly's ancestors. Sly even learned a new skill, the laser slide, in a chamber built by his late father.
At the heart of the vault, Sly was confronted by Dr. M, who had followed him inside. It was revealed that Dr. M was actually a member of the Original Cooper Gang with Conner Cooper and Jim McSweeney. He considered himself to be a tool to Conner at best and claimed that all Coopers must be the same. Sly objected, vehemently maintaining that he was not his father or any of his ancestors. The ensuing battle led to the vault's collapse, and Carmelita arrived to arrest both Sly and Dr. M. The doctor fired a laser blast at Carmelita, but Sly jumped in front of it and took the blast himself. Stating that "No one hurts my criminal!", Carmelita finished off Dr. M and jumped up to help Sly. As Sly came around, she discovered that he had amnesia, and had no memory of who he was. When he asked her, Carmelita lied and claimed he was her partner in law, "Constable Cooper." Believing her words, Sly and Carmelita escaped the vault, leaving Dr. M to his fate as it collapsed on him.
The gang looked for Sly to no avail. However, before going off with Carmelita, Sly managed to leave them with some of the Cooper treasure, his signature pouch and his cane. The Cooper Gang then went their separate ways, with Murray becoming a racing driver, Bentley hoping to build a time machine with Penelope and Sly beginning a new chapter of his life with Carmelita.
Some time later, Bentley is seen spying on Sly and Carmelita at a party with his binocucom. He catches a glimpse of Sly glancing back at him with a wink, revealing that he did not have amnesia. Bentley remarks on this with a closing remark: "That sneaky devil!"
Sly Cooper: Thieves in Time
After an undisclosed amount of time, Bentley contacts Sly and tells him that the Thievius Raccoonus was losing its contents, and that the only explanation is that somebody is messing with the past. After Murray is contacted, Bentley shows the two an invention that he and Penelope, who had gone missing some time before, had been working on: a time machine. However, due to the short time frame that they had to prevent further damage to the book, the design had been modified to fit into the Cooper Van and required an item from the desired time period to work. This prompted the heist of a nearby Parisian museum, which Sly was already eager to steal from, as his kleptomaniacal urges were coming to the surface. The gang broke into the museum and stole a Japanese dagger. As Sly was replacing the dagger with his signature calling card, Carmelita burst into the room, angry at Sly's switch back to crime. Dimitri was left in charge of the Thievius Raccoonus, as well as being in charge of determining where next to go in time.
The gang headed to feudal Japan and found that a dictator-for-hire, the tiger El Jefe, had set up and arrested Sly's ninja ancestor, Rioichi Cooper, for a crime that he hadn't committed. Sly entered the prison where he was being held using a disguise and rescued Rioichi. Back at the hideout, Rioichi filled the gang in on the workings of El Jefe. The gang then began working to free the village from the dictator's grasp. As they broke into El Jefe's stronghold, the tiger stole Rioichi's cane. Sly chased him up the fortress and battled El Jefe atop it. Before he could retrieve Rioichi's cane after beating El Jefe, he was ambushed by several rat troopers that were seen previously during the museum heist. They took the cane and were pulled up into a large blimp where a shadowy figure stood watching Sly. One of the rats carelessly dropped a sheriff's badge, which Sly took for use in the time machine.
The gang used the badge, which took them to the Wild West, the home of "Tennessee Kid" Cooper, who had also been thrown in prison by another time traveler, "Sheriff" Toothpick. To meet up with and rescue Tennessee, Sly got himself thrown in prison by vandalizing posters of Toothpick. In prison, Sly rescued Tennessee, who then told the gang about what Toothpick had been doing. Much to the entire gang's surprise, Carmelita was in the past with them, taken hostage by Toothpick. Tennessee, using his Rail Walk ability, rescued her, but in his absence, the rest of the gang was captured by Toothpick. Tennessee and Carmelita eventually rescued them, and Sly tried to explain himself to her, but she was still hurt by his betrayal. It turns out she had been sent back in time by Cyrille Le Paradox, the owner of the Parisian museum and the shady figure from before, while she was investigating his black market art dealings. In an attempt to stop Toothpick's gold train, the gang was sent over the edge of a cliff in the van. Thinking quickly, Bentley threw Murray's Aboriginal necklace into the scanner, which sent the gang to Australia, 10,000 BC.
Trapped in Gungathal Valley due to the crash sending parts of the time machine around the valley, the gang begins a search for the pieces. Carmelita, however, leaves the gang due to her anger at Sly. While performing recon on the area, Sly discovers that a black bear, Grizz, had been sent back to the ice age as well. Much to Bentley's surprise, Sly also finds a prehistoric raccoon who turns out to be his ancestor. Calling him "Bob," the gang promise to help him remove Grizz from the area, who had been stealing Bob's tribes only food source, pterodactyl eggs, for use as paint. Carmelita returns in time to help raid Grizz's base. After Murray defeats him, the gang uses Grizz's crown to travel to the medieval ages. Carmelita agrees to stick it out, as the Cooper Gang is the only way she'll be able to get back to the present.
Arriving in fourteenth century England, it is soon revealed that something is amiss. Robotic wolves are patrolling the streets and Sly's medieval ancestor, Sir Galleth, has been forced to work as a jester in the circus. Sly frees Galleth and tells the gang about the Black Knight, the tyrant who had arrived and taken over the kingdom with his robotic weaponry. He also had stolen Galleth's cane, which Sly quickly retrieves for him. As Galleth goes to a nearby cave to take on the Moat Monster, Carmelita follows him, which Sly notices, as he claims she never watched his back before. Carmelita responds, saying that she has, when she's tried to catch him. It is discovered by Bentley that the Black Knight is actually Penelope in disguise, which sends him into a depression. She had stolen Bentley's time machine plans and built the blimp that Le Paradox was using. Sly vowed that Penelope will pay for her betrayal of not just the gang, but Bentley. Taking on the giant Black Knight mech, Sly is able to defeat it, but is trapped by the debris. As Penelope comes closer, Bentley appears atop the castle in a mech suit of his own, built from the parts of the defeated Moat Monster. Bentley defeats Penelope and overcomes his demons, apologizing to Sly for not being there for him. Sly tells him to not worry about it and the gang heads to Arabia using a coin Carmelita had pocketed as evidence in the museum.
In Arabia, Sly finds a senior Salim al-Kupar. Salim was in a slump due to three of his friends and members of his gang, the Forty Thieves, being kidnapped. The gang set out to rescue the three. It is discovered that Le Paradox's plan is to forge documents in the past, which Salim's gang members had been forced to do, to give himself a royal lineage in the present. Finding where Le Paradox's blimp was docked, the gang headed there. Sly battled with the hypnotic Miss Decibel, Le Paradox's girlfriend (or so she thought), before the blimp took off with Carmelita as a hostage.
Back in the present, Sly sneaks aboard the blimp and finds Carmelita tied up in the darkness. Trying to release her, they are both trapped with a glass container. Le Paradox reveals that this container will be sent bouncing throughout time forever using his "time tunnel." As the two are trapped, Bentley and Murray travel back in time and collect all of the ancestors to help with releasing Sly and Carmelita. Sly fights Le Paradox as the time tunnel tears the blimp apart. Defeating the skunk, Sly is tricked by him and has his paraglider stolen. Without a way off the blimp, Sly turns back and heads inside.
Some time later, Sly wakens to the hot sun. It is revealed that Sly is now trapped in an unknown time period.
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