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The Contessa

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Now, just lay back and relax. Go to your happy place... and stay there... forever.
— The Contessa to Carmelita in the re-education tower[src]

The Contessa is a black widow, and a secondary antagonist in Sly 2: Band of Thieves. She was a famous, wealthy warden working for INTERPOL that was secretly a member of the Klaww Gang. She was the main antagonist of Jailbreak and A Tangled Web of Sly 2.



While a student majoring in criminal psychology, she fell in love and married a wealthy aristocrat. Nevertheless, only a few weeks after the ceremony, her beloved died of poisoning. Using her knowledge of criminal thinking and her newly inherited estate, she opened a rehabilitation clinic for criminals. The Contessa supposedly used hypnosis to cure criminals of their illegal urges, and gained a prominent position within INTERPOL.

Sly 2: Band of Thieves

The Contessa first appeared in Episode 2 at Rajan's ball, accompanying Inspector Carmelita Fox and Constable Neyla undercover. She later appeared with them at Rajan's spice temple, where she placed Sly, Murray, and Carmelita under arrest (after Neyla betrayed all three of them). Following her to Prague, Bentley bugged her with his sleep darts, which he had discovered would transmit the sound of her voice after making contact, resulting in her unwittingly revealing Sly's location in her prison. Later on, the two discovered that Murray was being held hostage by the Contessa who was working on controlling his mind with her hypnosis. Murray discovered her to be a secret member of the Klaww Gang, hypnotizing criminals to learn the location of their loot. She was also using illegal spice to help with the hypnosis and contributed hypnosis light wave generators to Arpeggio's blimp.

After failing to hypnotize Murray, the Contessa fled from her clinic and escaped to her castle estate, where she held possession of the Clockwerk Eyes and had Carmelita bound to an Iron Tech 250 in her re-education tower, where she tortured her and attempted to brainwash her with the Eyes.

Contessa Confronts Sly

Whilst the gang headed there to get the Eyes back, a war broke out between the Contessa and Constable Neyla, in which both had their own respective armies at their disposal. The Contessa's immediate plan, and one Sly and his friends would not allow, was to brainwash Carmelita with a Mind Shuffler into becoming her personal slave, so that she would take the fall at INTERPOL. However, Sly, Bentley, and Murray stopped her plans and Sly defeated her in combat.

Apparently, the Contessa knew all about Sly's family line, and even taunted him into fighting. Even after losing once and playing the innocent routine, she still declared herself mentally superior to Sly's gang. However, after fighting and defeating her for a second time, it is clear that Sly, Murray, and Bentley are a much tougher match. The Contessa is then arrested and stripped of her title.

She is mentioned by Arpeggio later on in the game when he reveals his master plan to Sly, speaking of her skills in hypnosis aiding the plan to hypnotize Paris. During the credits of Sly 2, it is said that after her incarceration, the Contessa became a highly successful real estate broker, with her clients displaying eerie hypnosis-like symptoms.


Physical appearance

The Contessa is a spider, possibly a Black Widow spider due to the recurring theme of an hourglass symbol associated with her character. She has the upper body of a human woman where the spider head should be and has claws instead of hands. She wears a red dress and also has a pocket on the back on her abdomen. It was assumed Contessa was Italian in origin, given her name means Countess in Italian. But further reseach showed she is of Czech origin, given the thickness of her voice and locations in which she chooses to live.


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Contessa defeated

The Contessa is highly intelligent and manipulative, able to trick INTERPOL into sending her criminals who she then steals from. She is also an accomplished hypnotist, able to hypnotize criminals into revealing where they hid their treasure. She is able to spawn spiders that can explode or attack her enemies. Her hypnosis is also increased by the Clockwerk Eyes, although strong minds, like Sly and Carmelita, are able to resist her. She is also skilled enough in fighting to temporarily hold her own against Sly, before being defeated.


Guard Type Weapon Description
Wolves Rooftop guard Mace Found in Episodes 4 and 5. Occasionally spawn from statues.
Bats Rooftop guard Fists Found in Episodes 4 and 5. Can call other guards.
Vultures Flashlight guard Crossbow Found in Episodes 4 and 5.
Shadow Guard Flashlight guard Crossbow Found in Episode 5. Elite variant of the vultures.
Tanks Vehicle Cannon
Found in Episodes 4 and 5. Invincible.




  • Contessa means countess in Italian.
  • The Contessa's estate, along with Jean Bison's logging camp and Mz. Ruby's swamp, is one of the paintings in Octavio's coffee houses in Sly 3: Honor Among Thieves.
  • The Contessa shares some similarities with Mz. Ruby: they are both cold-blooded animals, their levels have obviously mystic vibes to them, and they are both the only females in their gangs.
  • The Contessa is the only arthropodic boss in the series.
    • Although the Contessa is a [black] widow spider, she only has six legs instead of eight.
  • Across the bridge at the Contessa's Rehabilitation Center, a projector projects an hourglass, the symbol of a black widow.
  • The Contessa was originally planned to make a cameo in a cut-scene for Thieves in Time. At the end of the game where Bentley tells the players where all the character are now, Carmelita was shown beating up and arresting a criminal. The artist for the game said that he original planned The Contessa to be the one Carmelita arresting but but that didn't work out for various reasons. One of the artist on Deviant Art confirmed this on the artwork for the particular scene.
  • It is presumed that the Contessa poisoned her husband in order to obtain his fortune:
    • It fits in with the Contessa's animal theme, as the female widow spider is known for eating her mate after laying eggs.

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