But soon as all the money blows, all the pigeons take flight
With money comes fairweather friends. As long as you are wealthy, people are going to be friendly with you, but they would just as easily leave you when you lose it all: fairweather friends.
Mike Tyson is a big fan of pigeons and here Jay uses it to symbolize the loss of things a person may love when they go broke — such as material possessions, pets, lovers, etc.
Tyson specifically talked about this comparison between women and pigeons various times in his interviews, he even broke up with one of them for eating one of his pigeons!
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