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Gregory Alan Isakov – That Sea, The Gambler Lyrics 14 years ago
I may be way off, but it's worth a shot.

Perhaps it's about self discovery? The ocean is him, and he is sailing with all his might to try and find his way to land, where he will then understand himself. The journey he is choosing to take is a gamble, and the sea is a gambling fool, so would it make sense that the sea is just a part of him that he hasn't discovered yet? Could Mary be the person who he needs to make the journey work (for sometimes people have to find the right person in order to find themselves)?

I'd really like to know for sure what this song is about, because I highly doubt my cognition is good enough for me to do it on my own...

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