The short answer is that the doctor wanted to have plenty of supplies in the stockade. He wanted to get as much as he possibly could off of the ship. This would allow him and his men to hold out in the stockade for as long as possible.
So, for example, on the third trip from the ship, they brought gun powder, pork, and biscuits. They brought pretty much the same kind of stuff on the fifth trip. These kinds of supplies would allow them to defend themselves and to have enough to eat.
The doctor didn't think it was much of a risk because his side had better long-distance weapons than the pirates.
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