Sly and Bentley head to Venice, Italy to bring Murray back to the team.
Tropes:
- Arc Villain: Octavio.
- Bad "Bad Acting": Bentley marvels how Sly's disguise in the level is able to fool anyone because of his bad impression of an Italian accent.
Word of God claims that since Kevin Miller's attempt at an accent was legitimately terrible, so the developers had a joke written about it in the game itself. - Batman Gambit: The final step in "Operation: Tar-Be Gone!" relied on Bentley appealing to Octavio's pride as a singer and agree to a a singing contest with him, a turtle with no notoriety in such a field. Not only does Octavio actually take the bait, the plan would have gone off as intended if Carmelita didn't interrupt.
- Berserk Button: Don Octavio kicking Bentley out of his wheelchair causes Murray to snap and break his vow of pacifism.Murray: That does it! I'll floss my teeth with your spine!
- Blood Knight: Murray becomes this by the end.
- City of Canals: This being Venice, Italy, the whole level is built around this.
- Do Wrong, Right: When Sly threatens to knock Octavio's teeth out and force feed them to him, Octavio's only remark is how lame his threat is and that back in his day, he knew people would make you "pee [your] pants just by looking at him."
- Gangster Land: While there are the police (including Carmelita), its Octavius' task-force patrolling Venice.
- Guilt Complex: Murray took his vow of pacifism because he blames himself for Bentley being in a wheelchair. Bentley does not think the same. It takes Octavio attacking Bentley for Murray to break this vow.
- Hoist by His Own Petard: The Cooper Gang use the same black tar Octavio has been flooding Venice with against him in their fight against him.
- Living MacGuffin: Murray. Help him stop the pollution in Venice and he'll rejoin the gang.
- Old Master: On-top of being a skilled opera singer, Octavio is fast and strong for his age, able to do back-flips and get into a fist-fight with Murray on equal footing.
- Operation: [Blank]: "Operation: Tar-Be Gone!" involves Sly sneaking into the opera-house in-disguise and let Bentley into the pump-room where he destroys the tar pumps there. Bentley challenges Octavio to a singing competition as a distraction while Sly undoes the support to the chandelier, dropping it on Octavio. Bentley swipes the detonation switch from Octavio and they leave with Murray, Murray's pilgrimage complete.
- Putting the Band Back Together: The mission is all about bringing Murray back into the Cooper Gang. Taking down Octavio is just how they're going to do it.
- Rhythm Game: Bentley challenges Octavio to a duet as a distraction in "Operation: Tar-Be Gone!"
- Set a Mook to Kill a Mook: Sly and Bentley pit Interpol and the Vincenetti Gang against one another in "Turf War!" so that Carmelita would get rid of Octavio's security team for Carnivale.
- Skewed Priorities: In the Interpol Police Station, Sly comes up with the reasonable plan for him and Dimitri to disguise themselves as cops and just walk out the front door. Dimitri refuses on principle that it would cramp his style.Dimitri: Come on Man, I'm a fashion all-star! No way, no how I'm dressing up in a polyester pig suit... some things are worse than jail.
