What is known today as Jamaica College was opened in 1789 in the courthouse as the Drax Free School in the parish of St. Ann using a bequest from Charles Drax, a planter in the parish. He had come to Jamaica from Barbados in 1721 and when he died left money for the establishment of a charity school in St. Ann. Legal proceedings had delayed the handing over of the money to the St. Ann Vestry. In 1806 Walton Pen was purchased as the site for the school, which was given the name the Jamaica Free School by the Assembly in 1807.
In 1879, while Sir Anthony Musgrave was Governor, a law was passed to bring the school, then to be called the Jamaica High School, under the control of the recently constituted Jamaica Schools Commission. A new headmaster was appointed, the Rev William Simms, and the school was relocated from Walton Pen to Kingston in 1883. It was temporarily housed in the Barbican Great House, but in 1885 moved to the new buildings on Hope Road, which were opened on July 9 of that year.