Tell my brother, "Go to school in September"
So he won't mess up in summer school in the summer

from Wyclef Jean – Gone Til November Lyrics on Rap Genius

Meaning

He wants his girl to tell his brother to go back to school when school starts and do good so he won’t have to go to summer school and mess up.

Again, because of the nature of the work, he isn’t able to relay the message to his brother himself. He wants someone to tell his brother to actually concentrate on his studies during the year. If he doesn’t he will be back in school during the summer months when its fun.

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