School under construction, 1930s

In 1933, Trinity College School's newly appointed headmaster, Philip Ketchum, found himself in charge of an institution on the brink of bankruptcy. He spent the first few years of his tenure "cap in hand," trying to raise the funds to pay off a very onerous mortgage. But, through the generosity of a handful of alumni, the debt was finally retired.

Throughout the mid-century period, the School experienced tremendous growth in both admissions and facilities under the leadership of Headmaster Ketchum and Junior School principal Charles Tottenham.