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Astor lost money on the company. Astor asked a captain named Jonathan Thorn to lead his sea expedition. This was a bad choice. Thorn was impatient and wanted to find the passage as soon as possible. He sent a small dinghy to the mouth of the Columbia. At the time there was a rough storm happening. He killed eight men. He also left nine men on an island for being "unloyal". He had to be held at gunpoint to bring them back. On August 2, 1811, he also sunk the ''Tonquin'' and killed 61 men.

Only one of Astor's three expeditions, the second of his land expeditions, was successful. In that mission, the men sent out discovered the spot that eventually became Fort Astoria.