Villains

The chief inventor and leader of the Klaww Gang. He was the mastermind and strategist behind the Klaww Gang’s plan in Sly 2. Arpeggio grew up as a genius, however his body fell behind physically and he never developed the ability to fly. This made him angry and led him in search of a cure. At some point Arpeggio would develop an obsession with Clockwerk, and his desires became not only to fly, but immortality. He hid this part of his plan from the rest of the Klaww Gang, as well as his partnership with Neyla. After getting all the parts for Clockwerk’s body, Arpeggio would be betrayed by Neyla after she merged with Clockwerk’s body herself. Arpeggio would be crushed shortly after as Clock-La began to take flight.

Clock-La is a combination of the body of the infamous Clockwerk along with the mind of Neyla after betraying and deceiving both the gang and Arpeggio to get in this position. Taking down Clock-La is the last act for the Cooper Gang in the 2nd game, and it didn’t come without a cost, as a malfunction in the machine’s mouth after Bentley retrieved the Hate Chip powering it resulted in the paralysis in his legs. Once the Hate Chip was destroyed by Carmelita with Sly by her side, the still pristine metal body parts began to disintegrate before their eyes.

The ultimate villain of the Cooper Clan. Clockwerk is believed to be thousands of years old, and it was revealed was powered by a Hate Chip made from his hatred and envy for the Cooper Clan. Clockwerk is responsible for the murder of Sly’s parents and is believed to have killed numerous members of the Cooper Clan across time. Clockwerk was also the leader of the Fiendish Five, which were the villains of the 1st game. His body was used in the 2nd game by Neyla, before ultimately being defeated and having the Hate Chip destroyed. Clockwerk can be seen from a distance in Thieves in Time spying on the numerous Cooper Ancestors the Gang encounters in their respective time’s.

The Contessa was a secret member of the Klaww Gang while posing as a warden for Interpol. She was very intelligent and possessed hypnotic powers, which she would use to “reform” bad guys at Interpol, and she even tries to use it on Murray and Carmelita. Her hypnosis was also a crucial part in Arpeggio’s plan involving the body of Clockwerk as he was going to hypnotize all of Paris. However, Contessa would be arrested after being defeated by the Cooper Gang and her dark hypnotisms being brought to light.

Main antagonist of Thieves in Time. Traveled back in time to attack Sly’s ancestors and steal their canes, in hopes of erasing the Cooper Clan and replacing their lineage with his own. Sly would ultimately best him in the final showdown of the game.

Before joining the gang in Sly 3, Dimitri was a member of the Klaww Gang. He was the owner of a nightclub in Paris and used the Clockwerk tailfeathers as a way to print money.

Main antagonist of Sly 3. Dr. M turned out to be a member of Sly’s Father’s old version of the Cooper Gang alongside McSweeney. However, Dr. M came to resent Sly’s father and Cooper’s, and made it his life mission to break into the family vault on Kaine Island and steal the family fortune and legacy that had been stored inside.

El Jefe was a part of Le Paradox’s time traveling crew to take down the Cooper’s. El Jefe went to Japan to deal with Rioichi, and it’s likely that El Jefe is the one who poisoned the Shogun’s sushi to frame him. Despite his background as a high-ranking mercenary and military strategist, Sly would get the better of El Jefe and send him back to the present to be arrested.

The one responsible for kidnapping the Panda King’s daughter. General Tsao was an awful person, Sly even calls him the worst villain he’s ever face due to his lack of morality. Bentley even says that he saw Tsao kick a puppy twice.

Grizz is one with many unique interests from ice-skating, to painting, to graffiti, to rapping. He was one of Le Paradox’s crew in the time travel plan. He would go on to harass Bob Cooper in prehistoric times before the Cooper Gang would show up to assist Bob. Grizz would ultimately be defeated in a one-on-one encounter with Murray.

Member of the Klaww Gang. Jean Bison was entrusted with 4 parts of Clockwerk, the stomach, both lungs, and the talons. He used these on his trains in Canada so that they could run with no stoppage, dubbing them his “iron horses”. Jean Bison would ultimately capture the Cooper Gang after they had stolen 3 of his parts on the way to stealing the 4th and find that they had every single Clockwerk part. He would then sell all parts to Arpeggio for a wealthy price, and would then be confronted by Bentley. Bentley wasn’t happy with him selling the parts or Bison’s undermining of him, and Bentley would ultimately be victorious over Jean Bison in battle.

Captain of the vessel Death’s Head, LeFwee is known as the smartest man of the Seven Seas. He caught the gang’s eye due to the fact that he had stolen the diving gear that belonged to Dimitri’s father, and were helping him get it back. LeFwee was extremely self-centered and arrogant, however this would get him nowhere as he was bested by Penelope in a duel after he attacked Bentley.

A part of the Le Paradox’s time travel plan against the Cooper’s. Miss Decibel once had a bad performance, which resulted in her getting booed and caused her to throw a temper tantrum. This would result in her trumpet getting stuck in her trunk, and when she tried to remove it she realized that it now had the ability to hypnotize people. She would go on to use this to get people to do what she wants, including Salim Al-Kupar’s three fellow thieves. The gang would assist Salim in stopping Miss Decibel.

Member of the Fiendish Five. Muggshot grew up being bullied for his size and then hit the weights so that he could show the bullies what for. He ends up owning his own casino in Mesa City, before ultimately being arrested after being defeated by Sly. After some time, it’s revealed that Muggshot was somehow able to get out of prison when he makes a minor appearance at the ACES flying competition in Sly 3.

Member of the Fiendish Five. Mz. Ruby grew up as an outcast as most kids her age found her interests such as voodoo a little strange. She would go on to reside in the swamps of Louisiana before Sly would defeat her to take back the pages of the Thievius Raccoonus she possessed.

Turns out to be the main antagonist of Sly 2 and was a secret member of the Klaww Gang. Neyla was simply someone who couldn’t be trusted. She betrayed legitimately everyone who trusted her in the second game, from the Cooper Gang to her mentor Arpeggio. She would ultimately be the one to merge with Clockwerk’s body and form Clock-La. However, she would meet her fatal end shortly after as she was defeated by the Cooper Gang and Carmelita.

Mob boss in Venice, Italy. Octavio was a former opera singer turned mad man after the genre ended up losing popularity which resulted in his fame to decline. He was responsible for a black tar crisis in Venice that had completely ruined the water in the area. Octavio is also what ultimately what sent Murray back into action of his altercation with Bentley. The gang ultimately put an end to Octavio’s crime run and it resulted in him being behind bars.

Before assisting the gang in Sly 3, Panda King was a member of the Fiendish Five. In the first game he can be seen running cruel fireworks experiments that would often result in avalanches causing snow to completely encase towns with innocent civilians. After beaten by Sly, Panda King would at some point get out of prison, and go on to become a monk. However the history between he and Sly was still present and made their first few encounters tense in Sly 3 while recruiting him.

Penelope was technically a villain in Sly 3 as well however the Black Barron was primarliy just a way for her to bypass the ACES age restrictions for flyers. In Thieves in Time however, her intentions cannot be disputed. She takes on the mantle of the Black Knight and is aiding Le Paradox in his tirade against Coopers throughout time. She also claims that Bentley is too weak because of his morales, and won’t use the full potential that his mind is capable of. She was ultimately defeated by Bentley in a mech battle, but she certainly did significant damage to his heart.

Member of the Klaww Gang. Rajan started his life of crime at a young age selling spices on the black market, and it would expand as his business. He would dub himself the “Lord of the Hills” and attempt to convince others of his royalty. After his reputation was ruined at the ballroom party, he fled into the jungle to the heart of his spice operation and took on a noticeably more aggressive side. Rajan was ultimately defeated by Murray, and was arrested. However it is mentioned that after his prison sentence Rajan would go on to reform and establish a well-respected business across North America selling rugs.

Member of the Fiendish Five, serving as their chief machinist. Raleigh the only member of the five whose criminal origin story doesn’t originate from a rough childhood, and instead his own developed interest in piracy. Raleigh also had a blimp set above the sea that would cause harsh rain and winds to throw sailing ships off course known as the storm machine. Once the gang tracked him down Sly was able to take down Raleigh in the first stop on his journey in Sly 1.

Cohort in the attack on the Cooper Clan by Le Paradox. Toothpick grew up loving cowboys and gold, which led to him becoming specialized in gold robberies. With these things in mind, it’s no surprise Le Paradox wanted Toothpick going after Tennessee Kid Cooper. His trigger-happy combat style didn’t prove to be enough as the gang along with Tennesse were able to stop him. Toothpick is the only member of Le Paradox’s crew that gets permanently stranded in the past.