Bentley arrives in Prague to rescue Sly and Murray from the Contessa.
- All Up to You: The mission begins as Bentley as he attempts to rescue his friends.
- Arc Villain: The Contessa.
- Black Widow: Unsurprisingly, the opening cutscene implies that the Contessa poisoned her wealthy husband to gain control of his estate and fortune.
- Bleak Level: The level starts with poor little Bentley alone in the middle of an incredibly fortified Interpol Prison area with vultures, werewolves, gargoyles, spiders and a goddamn tank patrolling the streets, Bentley worried that his only friends will be reduced to nothing by the Contessa's brainwashing. Plus the music is pretty foreboding as well.
- Breaking Out the Boss: Bentley's first objective is to rescue Sly.
- Brick Joke: Bentley telling Sly that the Contessa's water tower was actually a robot. Sly doesn't believe him until the very end of the mission.
- Hellhole Prison: The Contessa's Prison was a maximum security criminal rehabilitation center located in Prague. The facility is heavily guarded and housed a large number of criminals whom the Contessa had collected over time. It also doubles as a Bedlam House, as Contessa uses hypnosis to "rehabilitate" the criminals there, the methods used being very psychologically questionable, made even more so when it is revealed that the Contessa uses these "treatments" so that they could tell her where they hide the things they steal and keep the profits.
- Highly Visible Password: One mission requires you to trigger the alarms to lure a guard to deactivate them, at which point you can photograph the passcode, which is displayed in enormous digits just above the keypad.
- Humongous Mecha: The Contessa has a giant attack robot to guard her prison. It's cleverly disguised as a water tower.
- Meaningful Echo: In the prologue mission, Bentley gives himself the codename "Wizard" to deal with his nervousness. After Sly gets out of jail, he decides to call Bentley that.
- Operation: [Blank]: "Operation: Trojan Tank". Using the Contessa's keys, Sly and Bentley will steal one of her tanks (Bentley drives and Sly hides under it) and the guards will allow them inside. Bentley blasts the security doors open for Sly who will then sneak his way to the control center and frees Murray from there.
- Punctuated! For! Emphasis!: "What did I tell you? Giant. Attack. ROBOT!"
- Überwald: Set in Prague, the entire level is a massive nightmare full of gothic architecture, perpetual snow and red-lightning, spiders and a Hellhole Prison owned by an anthropomorphic black widow spider guarded by werewolves, gargoyles and vultures.