The plot of The Piano Lesson by August Wilson develops in 1936 at Pittsburgh after the historical background of World War I followed by the period of ‘The Great Depression’ and later World War II, actuating ‘The Great Migration’. A large number of African American populations relocated from South to North America in a quest of better life, economic welfare, freedom from slavery, job opportunities, good status, sophisticated neighborhood and security in that period till the migration got reversed around 1965. Our essay sets out to review significant features of ‘The Great Migration’, its implication on lives of African-Americans and challenges they face to survive economic devastation, through analysis of the play ‘The Piano Lesson’ that represents a clash between two siblings, Berniece and Boy Willie, over a century old piano with emblem of African sculpture, symbolizing a conflict over preserving their legacy and finally conveying the lesson of embracing their history to pioneer a positive and hopeful future. The drama starts with Boy Willie and his partner Lymon entering Pittsburgh from Mississippi to make money by selling watermelons and a piano for purchasing Sutter’s land where his ancestors worked as slaves. These youngsters exemplify the first of their generation whose ideas were driven by capitalism drifting away from culture, since they believe that “freedom is defined by money”.