VERDICT: He was heading to an active Fort when a skeleton sloop popped up so he tried to ram them. He had the barrels stacked on the spar by that point, and none of them blew up on impact, so he shot them, which did sink the skeleton sloop but also sunk him. He was all JUST AS PLANNED and hopped into his rowboat to collect the skelly loot, but then could not find it, and also lost his rowboat. He also did not know which direction the nearest outpost was.
I will let you draw your own conclusions.
Haha, sounds about right. That was definitely a stupid thing to do, but it was still funny and fun. Any other ship could have easily sniped one of those barrels, or a single skele cannonball, a single Megalodon bite, even a collision could have set them off.