Lyric discussion by thriggle 

This is probably too specific to be the only possible meaning of the song, but the lyrics make me think of Stede Bonnet, the gentleman pirate who palled around with Blackbeard and whose criminal career was little more than the series of failures. He left a good place in society (not to mention his home and wife) in order to pursue the adventurous life of a pirate. He and Blackbeard were obtained pardons together, but while Bonnet was waiting for a letter of marquee to become a legal privateer against Spanish shihpping, Blackbeard took off with his ship (which for some reason prompted Bonnet to return to a life of piracy instead of getting the letter of marquee).

Similar to Bonnet, the singer rejects a comfortable life ("don't sell me anything," and "I don't want your life insurance"), expresses a desire to be alive and exciting, and seems to fear being forgotten ("speak of me in the present tense"), powerless ("or rather, fistless"), and left behind (the way Blackbeard, a real "profiteer," left Bonnet behind).

As for the confession, Bonnet's own boatswain, Ignatius Pell, somewhat reluctantly testified against him. Bonnet was put to death (despite begging for mercy and his promise to have his own arms and legs cut off), dying with neither glory nor dignity.

The song comes off as a rejection of material security in favor of some other life, possibly a life of adventure and comradery. But it also seems to encompass a sort of sadness associated with the end or failure of some glorious endeavor (both in the line about the leaves having fallen and in the multiple references to an ominous, pending confession). There is also a sense of betrayal in the lines "I can see you're just a little privateer/profiteer as your confession draws near."

Pretty and sad.

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