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The trustees now decided to improve the status of the Monoux School. They advertised for a grammar-school master, able to teach the classical languages in accordance both with the 1659 Commission and with what they conceived to have been Monoux's intentions. The person appointed was Rev. F. Parsons, who lasted no more than a month or so, and he was replaced by Rev. J. F. Roberts, who appears to have arrived in March 1820. He was previously Second Master at Felsted School, where the First Master, Rev. E. Squire, had at that time (1813-29) completely run down the charity school provisions and substituted a fee-paying boarding school of his own devising in the premises.

The name of Roberts has been much vilified, and some strange misconceptions have been accepted of the running of the school during his time, the most popular of which is that the numbers taught were reduced at one time to five boys. Roberts, it is certain, ran the school for his own profit. After his arrival, he changed the course of instruction, such that the boys then in the school were taught quite different subjects. He also increased the charges for extras to between 20s. and 44s. per year, with the result that most of the scholars left forthwith. From then on, he taught Latin and Greek free of charge, but made a charge of six guineas a year for instruction in English, History, Geography, Mathematics. In doing this he had adopted the Felsted system in its entirety. Roberts therefore altered the whole outlook of the school. His real purpose was to take boarders, outside the foundation, and teach them at a much more remunerative rate, together with a few local boys. He took a house in Church Lane, identified as the Walnuts, opposite the Ancient House. The Chestnuts nearby has also been suggested as his base; perhaps he moved about as the size of his establishment varied. There he ran a boarding establishment, seemingly holding some thirty boys at any one time. Teaching, however, took place in the building belonging to the foundation.

Of this period we have a remarkable narrative by Edward Berthon, clergyman and marine inventor. He was the son of a London merchant, with Walthamstow connections, who had become bankrupt. Edward was sent to the Monoux School in 1820, after a spell in a larger private school in Wanstead. He was nine at the time and the youngest in the school. The boarders seem to have been ill-fed and strictly taught, but Berthon himself later went on to Cambridge, as did some of his contemporaries. The schoolroom over the almshouses is described as "a wretched draughty loft, with a steep open-tiled roof". He describes a riot in the boarding house and its consequences; Roberts threatening to flog the whole school and, after some hectoring, commuting the sentence to a thousand lines. One of Berthon's memories concerns the long board, still in the present School's possession, reading "Georgius Monox, Eques, hanc Scholam fundavit, AD 1527", which he says "was nearly three hundred years old". If so its inscription must have been renewed, for the "s" of "Eques" is painted as "f ", in the style of the eighteenth century. Roberts was doing no more than schoolmasters up and down the country were doing. Many a Tudor institution was converted into a reputable school by the same process; but he might have succeeded more had he been less restrictive in the course of education offered to the free scholars. Something of the kind happened at Chigwell School and at the Colchester Royal Grammar School, these schools prospered greatly later in the century. As it was, his method of expanding the profitable boarding side at the expense of the foundation led eventually to his removal in 1836, shortly after the Charity Commissioners' Report.