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Possibly a song about NYC and how history repeats itself? The 99 year lease and wooden gate/real estate could refer to the first Dutch settlement where they got the land for a handful of beads.
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Thinkin' of a master plan
'Cuz ain't nuthin' but sweat inside my hand
So I dig into my pocket, all my money is spent
So I dig deeper but still comin' up with lint
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