To defeat Don Octavio, wait for Sly's signal to lure Octavio to the tar pit. Get close to the tar pit and wait until he gets stuck in the tar, then punch him rapidly. Don has three attacks. He will ram you, punch you, and when half his health is depleted, he will send a sonic boom toward you. Once his health is half depleted, you will have to run to another tar pit. Hold R1 to sprint and follow Sly to the next pit. Run away or sidestep when he tries to charge at you, and back away when he punches you. To dodge the sonic boom, jump over it or back away from it.