Harold Woodson Lorin was born in Christiansted, St. Croix to Ebenezer (deceased) and Claudia Willocks. Willocks attended the public schools of St. Croix and graduated from the St. Croix Central High School in 1975. He enrolled at Morgan State University in Baltimore, Maryland, in the spring of 1976 and earned his Bachelor of Arts degree two years later in 1978. In 1979, Judge Willocks attended the Howard University Graduate School of Political Science. The following year, he attended Howard University of Law. He interrupted his studies and returned home for two years. He resumed his educational pursuits and enrolled at Antioch School of Law, completing his Juris Doctorate in 1987.

Judge Willocks' experiences and service stretch over thirty years. For periods of time between 1978 and 1985, he enjoyed the rewarding profession of teaching at Elena Christian and Arthur Richards Junior High Schools and at his alma mater, St. Croix Central High School. In 1987, he became a local prosecutor. To further his challenge, he then switched in 1988 to become a territorial public defender. In this capacity, Judge Willocks handled hundreds of cases involving the indigent population of the Virgin Islands. After four years, he ascended to the rank of Chief Public Defender of the Virgin Islands, where he took on the challenges of bringing the Public Defender's Office into the 21' century. For a period of time during his tenure as the Chief Public Defender, the office of the Territorial Public Defender had one of the highest jury trial win ratios for a Public Defender's office in the nation.

In August 2009, Willocks was nominated by the Honorable John P. de Jongh, Governor of the Virgin Islands of the United States, to serve a six-year term as a Judge of the Superior Court of the Virgin Islands. Willocks was later unanimously approved by the Legislature of the Virgin Islands.  He was reappointed by the Honorable Kenneth Mapp, Governor of the Virgin Islands of the United States, for a second term and reappointed by the Honorable Albert Bryan, Jr., Governor of the Virgin Islands of the United States, for a third term.  He has served as Administrative Judge, Presiding Judge, and as a Senior Sitting Judge of the Superior Court. 

On January 22, 2024, Judge Willocks was nominated by the Honorable Albert Bryan, Jr., Governor of the Virgin Islands of the United States, to serve a ten-year term as a Justice of the Supreme Court of the Virgin Islands.  On March 25, 2024, Judge Willocks was unanimously confirmed by the Legislature of the Virgin Islands. 

Judge Willocks has written over twenty books. His most well-known books, The Umbilical Cord, from Pre-Columbian to the Present, Civicus, Over the Horizon, and The Virgin Islands, are currently used as textbooks in many public and private schools throughout the territory.  In addition to his many books, Judge Willocks has also written numerous articles and papers.  He is a lecturer and presenter in Virgin Islands History and law.

Judge Willocks has assisted various community organizations, especially those dealing with the youth. He spearheaded the Virgin Islands History, Geography, Civics and Character Enhancement Bowl and the Prevention through Education Summer Camp. Some of the honors bestowed upon him include the Virgin Islands Humanities Scholar and a Virgin Islands Cultural Bearer. He has been one of the leading advocates for educational programs and activities for the youth of the Virgin Islands. He played a vital role in the establishment of an expungement statute for the Virgin Islands, and the Virgin Islands Behavioral Health Bill.