Peachy now asks who's going to sit out for Drake, and he's told that Jon and Michelle will be the chosen ones. The team members now arrange themselves in the little boats. Ryan-O, Osten, Rupert, and the Best Buds (Shawn and Burton) are each taking charge of a boat, with the chicks and Andrew scattered among the boats. I say that only because that's the way they shoot and present the thing. The first notable event once the boats get tangling with each other is that Osten almost falls out of (and sinks) his own boat. Nice. Trish manages to pull a plug out of one of the Morgan boats. Osten pulls a plug from the Rupert boat. What Osten, Lill, and Tijuana don't seem to realize is that once your boat gets a couple of plugs pulled, it's mostly a race against time to keep your boat afloat as long as possible, and one of the things you want to do here is keep your boat as level in the water as you can, which minimizes the water coming in. Osten instead positions himself in the corner of his boat, and Lill winds up near him, so they've got the corner of the boat pushed so far down in the water that they're basically sinking themselves. Once Osten gets his boat backed away from everyone and his group once again gets the boat more level in the water, things start to look up for them. Elsewhere, Rupert works on pushing the Ryan-O boat down with the hook.
Osten continues to miss the point completely, and he stands up in the very corner of his boat in order to push down on the Best Bud Boat with the hook. This causes his boat to dip below the surface again and start to fill rapidly with water. The S.S. Osten quickly sinks, leaving the two Drake boats to once again gang up on the Ryan-O boat. I want to point out here that Rupert is, as usual, relying entirely on what a stud he is by pushing down with the hook, which doesn't look like it works very well. The Ryan-O boat seems pretty unaffected by Rupert's pushing, and only gets in trouble when there are two boats ganging up on them. What actually happens is that Ryan-O gets himself standing up (not smart), and Andrew gets himself cornered on the side of the boat that's next to the Best Bud Boat, and specifically, next to Sandra. Ryan-O and Andrew start to tip the boat over in that direction, and Sandra capitalizes by pushing down on that side of the boat with the paddle. In an overzealous effort to keep the boat balanced, freaking Andrew leaps over to the other side of the boat so fast that he makes Ryan-O trip and tumble over to that side of the boat as well. When Ryan-O and Andrew hit the same side of the boat at the same time, that throws that entire side of the boat (the Rupert-boat side) underwater, and once that happens, the boat sinks quickly. Up until that point, Rupert's approach wasn't working, because he was determined to just try to force the boat underwater, which you really can't do, because you just can't apply very much force unless you stand up, and if you stand up, you sink yourself. Oh, and Darrah was also throwing buckets of water when she should have been bailing. So in the end, Drake did win this challenge, but mostly because Osten the Physical Asset and Andrew the Rotting Fish Head are stupid. Anyway, Peachy calls the challenge for Drake, giving that tribe four in a row. Trish raises her arms in victory. Jon and Michelle happily dive into the water to help their team celebrate the victory they had nothing to do with. Peachy reminds Drake that they will be getting the pillows and stuff, and that they will be sending somebody to collect from the very nearly judgment-proof Camp of the Damned. The members of Morgan look around miserably. Rupert pumps his fist, of course. Trish triumphantly raises her arms again. Or else they just show it again.