Though there is nothing political or colonial about Squire Trelawneys expedition, flags appear frequently in this novel. Since Treasure Island is not being claimed as a British Terittory, the function of the flags seems more symbolic than political.
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The flags are symbolic in that they represent authority. There are two types of flag in the novel..... the skull and crossbones, which is the pirate flag, represents Silver's authority, and the British Union Jack. While the pirates control the ship, Silver flies the skull and crossbones. The pirate flag is quickly replaced when Smollett and the other men retake the ship...... and Jim makes sure that the pirate flag is the first thing to go.