Winthrop "Toby" Dakin (after whom Dakin House was named), was one of the original trustees of this institution. In 1965, he was a charter member of the Trustees of Tinker Hill, incorporated to acquire land for the new college. Tinker Hill is one of the foothills of the Holyoke Range located just to the south of the main campus, and was the site of an Amherst College ski slope at the time. Lacking a name for the new college, then just in the early planning stages, the body was named obscurely to prevent land prices from soaring, as the trustees feared they might if the landowners discovered that a new college was in the works. Toby Dakin, a Harvard educated lawyer with a long time practice in Northampton, was of immense assistance to the fledgeling college in negotiating with landowners, drawing up contracts, and dealing with the state bureaucracy.
After the trustees hired Franklin Patterson as the first President and settled on the name Hampshire College, Toby continued to serve as a trustee, giving the college the benefit of his local and legal knowledge and the wisdom of his experience. A Latin scholar, he took on the task of devising a motto for the new college, working from a suggestion by Dick Lyon, the first Dean of the College, who quoted a line from Santayana, "It is not wisdom to be only wise..." His Motto Memo, in which he details the results of his research and consultation with other Latinists, is a classic.