So, Staples High School is looking for a new principal.

James D’Amico — the popular administrator who held the post since 2016 — is moving north to his alma mater, New Fairfield High.

D’Amico succeeded another popular principal. John Dodig, recently retired after a long stint at one of Fairfield’s high schools, was hired in 2004 as an interim. He liked the school and town so much, he applied for the permanent position. He stayed 10 more years.

Overall, Westport has done an excellent job hiring high school principals (no easy task). From Doug Young and Stan Lorenzen — firm but fair men, perfect for their 1940s through early 1960s times — to Jim Calkins, another interim choice who turned out to be a progressive, modernizing force while shepherding Staples through the turbulent late 1960s and early 1970s — our district has, more often than not, put the right people in charge of our flagship school.

Of course, hiring practices have changed since Horace Staples founded his school in 1884.

The first principal, James Tufts of Amherst College, lasted just one year. He found it difficult to work under Mr. Staples, and developed typhoid fever.

In 1885 Wilbur Cross — a young man who, upon graduating the previous month from Yale University, planned a literary career, yet understood the necessity for a teaching career so he could support himself — heard that Staples needed a principal for his new school 30 miles away. In his autobiography “Connecticut Yankee,” written 58 years later, Cross recalled calling at Staples’ office.

The young man spoke into the mouthpiece of the older man’s ear trumpet. The school benefactor made clear “with cold civility” that he preferred an “Amherst man” from Cape Cod for the position. However, the appointment would be made by a committee, comprised largely of clergymen.

Cross sought out Rev. Alonzo Lewis, rector of Holy Trinity Church. The reverend was an 1852 Yale graduate and a member of the same Psi Upsilon fraternity to which Cross belonged. The two men talked in Lewis’s library, smoking corncob pipes and sipping hard cider until 3 a.m. Cross got the job.

When he called on Staples to accept the position, the housekeeper was away. There was nothing in the pantry to eat but bread, butter and fig pie, so they enjoyed a cask of excellent cider instead. As they discussed their impending partnership, an important issue arose: the salary.

The founder said he would contribute $600 toward operating expenses of his school, while Cross would receive all tuition fees. With an enrollment of 60 students, that was expected to be $800. However, Cross also had to pay for heating the building ($400), and a part-time janitor ($300). “If all went well, there would be left $700 for my services,” Cross later recalled.

At that point Cross, 23, and Staples, 84, “began to dicker.” In the end, Cross said, the “old Yankee ... promised to pay for the janitor.”

Cross took the job. He stayed only a year, but it was memorable enough that he devoted seven pages to it in his autobiography. Enrollment increased, which “pleased the old man.” They developed a close relationship.

Cross appreciated some of Staples’ thrifty quirks. Staples, in return, agreed to pay $300 for chemistry and physics equipment, simply because his principal asked for it.

Following the custom of the day, Cross was an active principal (“principal,” in fact, meant “principal teacher.” His assistant was simply the second — and only other — teacher). Cross taught Latin, Greek and geometry, and introduced English literature “at a time when the study of English in high schools rarely extended beyond grammar and composition.”

He recited great passages from Shakespeare, Milton, Wordsworth, Byron, Keats and Shelley, and encouraged his students to memorize something from every poem.

At the end of the academic year Cross accepted a fellowship at Yale to study English literature and philosophy. He stayed in New Haven for many years, becoming a professor of English, the first dean of Yale’s graduate school, and a well-known critic of English literature.

In 1930, age 67, he was elected Connecticut’s first Democratic governor in 15 years. In 1941, in recognition of the governor’s support for the Merritt Parkway, its extension toward Hartford was named for him. His name also graces a building at the University of Connecticut, whose growth he supported during his term in office.

Apart from Cross’ autobiography, few records remain of the earliest years. In 1886, he recommended fellow Yale man Thomas C. Stearns to replace him as principal.

Nearly 135 years later, we’re looking again for a new principal. Perhaps another Yale man — or woman.

Dan Woog is a Westport writer, and his “Woog’s World” appears each Friday. He can be reached at His personal blog is