I beat him and got a trophy as well as a special gear item. Then the cutscene continued as if normal. So no matter what you end up losing, kinda. It's a scripted loss. Then the game begins. Took me 3-4 tries.
Commodore Matthew Perry was the American who led the initial "trade envoy" (you can read that as military occupation force if you like) to Japan that eventually triggered the Meiji restoration.
why would he be on a ship talking about Claiming Japan as if it's a Whale? He's a Forigner come to open it's trade borders to the rest of the world. learn history.