I just can't lose when I was young I was like Fresh
Poppa raised me to chess moves
This references the 1994 movie “Fresh” in which the protagonist, a 12 year old drug dealer, isn’t allowed by the court to see his father. To get around this, his father meets him in the park where they play chess against each other. His father tries to teach him about life by using the chess pieces as metaphors for real life.
Notice all of the chess references at the end of the verse. Some of these statements are similar to lessons imparted by Samuel L. Jackson, who plays the father in the movie.
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