Octavio: Ah, Mr. Tomato Fertilizer. You got a death wish?
Bentley: I couldn't resist showing you up at what you love most... opera singing!
Octavio: You're a vocalist? Fine, a duet is coming up. We'll sing first and then I'll gut you.
― Before their duet[src]
The time has come for the gang to put an end to Octavio's tar-pumping schemes and get Murray back on the team.
Part 1 - Destroying the tar vacuum
The first objective is for Sly and Bentley to get inside the Opera House and destroy the tar pipes. Sly uses his disguise on the guard standing at the front entrance. Once inside, he makes his way through a room, then a hallway leading to a double-button security door. Octavio comes through the door and, not recognizing Sly, asks him for a password. When said correctly, he orders Sly to pass it on to his other men that he does not want to be disturbed during his recital for any reason. Sly abides by his command and asks for assistance in getting the door open. Octavio helps him get the door open and tells him to be quick in there so he will not miss out on the recital.
Once inside and away from Octavio, Sly heads downstairs to the pump room and lets Bentley in through the side door. He then takes off his disguise. Bentley now needs to quickly destroy the six tar pipes in the room. Once done, the main tar vacuum will start to lose suction. As Bentley bombs each tar pipe, reinforcements show up and Sly fends them off, leaving Bentley to continue destroying the pipes. Once done, the two head outside for the next objective.
Part 2 - The recital
Bentley must now get on stage with Octavio and sing in the recital with him. Meanwhile, Sly must cut the ropes to the chandelier to drop it on Octavio's head, which will allow them to swipe the demolition switch from him. Bentley confronts Octavio walking onto the stage. He tells him he cannot resist showing him up at his own talent. Octavio lets him perform and threatens to gut him when it's over. Bentley gets on the stage next to Octavio. Sly hops onto the top of the stage, ready to cut the ropes to the chandelier.
The recital now begins. As the two are singing, Sly starts cutting the ropes. Within each quarter of the performance, Octavio draws closer to Bentley, readying to finish him. Once the recital ends and right as Sly cuts the final rope, Carmelita crashes the party and shoots out the chandelier, before it hit Octavio. She tells everyone to freeze. One of Octavio's men arrive in a boat and Octavio hops in, still in possession of the demolition switch. Sly and Bentley hop into the police boat they used earlier and chases after them. Carmelita starts shooting at them, then calls her mercenaries for an immediate helicopter pickup.
Part 3 - Boat chase
Once in the canals, Bentley must shoot out Octavio's engine to disable him. During the chase, Carmelita shows up in her police chopper and tells them to stop their engines or she and her squad will be forced to use lethal force. They then double back to town. The chase continues and Bentley finally shoots out Octavio's engine, causing his boat to lose control and start swerving all over the place.
Part 4 - The fight
When they return to town, their boat jumps the curve and crashes into the stage, bringing the whole thing down. With Octavio beat, Sly bargains with him, saying they will all ditch the cops together if he gives up his demolition switch. Despite spending 6 months to prepare the device, Octavio does not mind, stating he has more where it came from. Murray, who watched the incident from atop a building, comments on how cool the destruction was. Octavio shows him what cool really is and presses the demolition switch, which blows up a building on the outer edge of town. Octavio then approaches Bentley and knocks him out of his wheelchair. Sly asks Murray for his help as he has never seen anyone move that fast. Murray is still reluctant due to the promise he made to his Guru. Sly tells him the water will clear up any minute, and insists that they both of them take Octavio out. Bentley, slightly conscious, softly cries for help. Seeing him in pain is finally enough to break Murray out of his peaceful rut and draw the line. He even deliberately breaks the teeth on his necklace, proclaiming that he will use Octavio's spine as a floss. He jumps downs and gives Octavio a good punch, briefly knocking him unconscious.
Murray and Octavio engage in a fight. Octavio is too fast to be fought, unless the gang uses the tar to slow him down. Once half of Octavio's health is gone, the tar valves become empty and they must run to the police station to find another one. The fight then continues there. Murray finally knocks out Octavio, who then passes out. With the demolition switch in hand, Murray and Sly run back to get Bentley before the cops close in. Octavio is now defeated and the operation is a success.
- It is possible for Murray to land hits on Octavio while he is free of the tar, but they do no damage to him.
- Murray can use his Temporal Lock move on Octavio, but the latter will break free from it to avoid a punch thrown at him.
- The secret soprano password that Octavio asks for is the same as the Carnevale password.
- In alpha versions of the game, it was Sly, not Bentley that was knocked down, and Bentley was the one helping Murray defeating Octavio. This was later changed in the final game to be the reverse.