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His family joined the Great Migration, when tens of thousands of blacks left the South to seek opportunities in the more economically prosperous northern and mid-western industrial cities.
After his mother became incapacitated by a stroke, Richard was separated from his younger brother and lived briefly with another uncle.
Later, he was called to the principal's office, where the principal gave him a prepared speech to present in place of his own.
Richard challenged the principal, saying "..people are coming to hear the students, and I won't make a speech that you've written." The principal threatened him, suggesting that Richard might not be allowed to graduate if he persisted, despite having passed all the examinations.
In September that year, Wright registered for mathematics, English, and history courses at the new Lanier High School, constructed for black students in Jackson.
(The state had segregated schools under its Jim Crow laws.) He had to stop attending classes after a few weeks of irregular attendance because he needed to earn money for family expenses.
In 1916 his mother Ella moved with Richard and his younger brother to live with her sister Maggie (Wilson) and her husband Silas Hoskins (born 1882) in Elaine, Arkansas.