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You never do kill him : he always escapes.

When you have the most powerful ship (Phoenix Warbird), the Shipwright and the Cannoneer, sail around the new island, Skullduggery, and the recognizable ship of Captain Crawfish will attack. If you are able to reduce his ship's "health" to zero, he sails away in defeat. Then you can return to Fort Ridley and get the shovel and treasure location.

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Q: How many times do you have to kill captain crawfish on Skullduggery Island?
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