Since the passing of A. Leon Higginbotham, Jr. in 1998, many have wondered what the award winning author, longest-serving black federal judge, first black to head a federal regulatory agency, recipient of the Spingarn Medal and the Congressional Medal of Freedom, and author of the famous “Open Letter to Clarence Thomas” would think of the state of race relations today. Appointed to the Federal Trade Commission in 1962, Higginbotham served in several powerful federal positions including Vice-Chairman of the National Commission on the Causes and Prevention of Violence, member of the first wiretap surveillance court, and chief judge of a United States Court of Appeals. Known as the conscience of the American judiciary on race issues, Higginbotham caused controversy in 1992, when he publicly reminded Justice Clarence Thomas of his predecessor’s contributions to racial equality. In the 18 years since this public letter, much progress has been made, including Higginbotham’s former student, Michelle Obama, becoming the first black first lady. This article presents what might have been Higginbotham’s letter to President Obama after one year in office.