The Striker Sisters is one of about twenty known works painted while Earl was in debtor's prison. From September, 1786, until his release on January 29, 1788, he resided in New York's City Hall jail. What might have been a nightmarish episode was first alleviated and later ended by the passage of An Act for the Relief of Insolvent Debtors, April 13, 1786, and the formation of a Society for the Relief of Distressed Debtors, January, 1787. Members of this society sent their wives, children, and friends to be painted by the prisoner, thus furnishing him with the means to secure release. Earl's most famous sitter during his confinement was Elizabeth Schuyler, daughter of one of George Washington's generals and wife of Alexander Hamilton. While incarcerated, Earl also painted many of the presiding officers from his trial.