Apparently, in order to complete the crossing, you have to start in the middle of the night and with very calm conditions. There's a boat out ahead of him and a kayak paddling next to him. Both are using floodlights so that they can see where he is, and that begins drawing attention from squid.
OK, that's all the setup you need. Now here's Spalding telling the story of what happened when the cookie cutter attacked:
Spalding: I was swimming along in perfect conditions. The wind kicked up a little and I was hoping that it was a local condition that would disappear. We were on 30 min feeding schedule. At 8:15 I was trailing the boat by about 80 to 100 yards. The boat captain liked to run ahead and then go out of gear and wait for me to catch up. On the previous feeding stop he complained about not being able to see the Kayak and requested we turn on our emergency light so he could see us better. He also turned on his cabin lights at the same time. 15 minutes after we turned on the lights and I had my feeding I started to feel squid bumping into me. I assumed they were squid as they felt soft. I did not like this at all it worried me. It felt eerie and was waiting for something more dramatic. There was nothing I could do at this point but put my head down and do my job. After the 4th bump I felt a sharp prick just to the left of my sternum. It was excruciating and I gave a yelp. As soon as that happened I knew I had to get out of the water and the swim was over. I reached the front of the kayak and turned off the light and started climbing into a one person kayak. As I was about to push onto the kayak I felt a hit on my left calf. I ran my finger down my leg and felt a 2.5" by ¾ inch hole where I had been hit. I continued getting out of the water with blood everywhere. We called the boat on our radio and they were on us in a minute. I got off the kayak and into the boat and they put gauze and duct tape on the bite as the boat charged full blast to Kehei boat ramp. I was extremely disappointed to have to abort the attempt. As soon as I could get my wits about me I know it was a cookie cutter bite and the captain also concurred.
Dove: Did you go back and try the swim a second time?
Spalding: I waited 2 years for my second attempt. The healing process took 5 months and then I had to regain the conditioning that I lost in the healing process. I also had a number of other things that I had put on hold training for the first attempt that came up on the agenda limiting the amount of time I could commit to training. Again I started looking for the ideal window of weather and this time planned the swim to avoid being in the same place in the dark. I planned the departure for 3 am which would keep me in shallower water in the dark and allow me to land with minimal dark swimming. At almost the same location as the bit I encountered an oceanic white tipped shark. They are more feared to me than a tiger shark. I knew their reputation as a opportunistic hunter and became wary when it showed up on the scene. I watched it as it came in to get a look and then disappeared only to reappear at my rear some minutes later. It finally left for good but I was on full alert for the rest of the swim. The biggest obstacle to completing the swim was getting hit by a Portuguese man of war 5 hours from the end of the swim. This was very painful and created spasms in my leg and stomach. I kept swimming and a few hours later the pain subsided. Three miles from shore in the dark I was bumped by a fish. This got my speed up and I was thankful it did not return.
[Mr. Spalding completed the swim in 19 hours and 43 minutes, landing at Nu'u on February 27 at 10:43 PM]
Want to avoid a similar fate to Spalding's? A shark researcher offered this appropriately snarky response, "Don't swim at night, over a deep sea trench, while being lit from above by boat-based floodlights."
I think I can manage to avoid this situation.