James Waugh was chairman of the school committee from foundation until 1883. James Corrigan was the first of seven Headmasters in Wesley's first 35 years. The school struggled for numbers over some of this period. The Depression of the 1890s provided a particular challenge when Arthur Way was Headmaster, and came to a head in 1896 under Arthur Stephenson when enrolment dropped to 90 boys and closure was threatened. Thomas Palmer's tenure as headmaster was curtailed early in 1902 after he was found to have embezzled more than £1,000 of the school's funds.