AN INSTITUTION WITHIN AN INSTITUTION

A look into the life of Arthur Sheriff as an inspiration for the Academy.

BELOVED EDUCATOR

Arthur N. Sheriff spent more than half his life at Cheshire Academy. During his 52-year career as teacher, dean of students, and headmaster, Sheriff ’s deft ability to guide students’ individualism was the impetus for the Academy’s studentcentered educational model.

Perhaps Sheriff ’s skill as a mentor and leader can be traced to his childhood in Chicago. Records from the 1910 U.S. Census show Sheriff, his mother, and his three younger siblings were supported by his father Arthur G., who worked as a selfemployed china painter.

A 1909 article about the 21-year old Sheriff from the “Marietta (Georgia) Journal” contains the headline, “Poverty a Spur to Education.” The article noted that when he was just 15 years old, Sheriff left school and went to work as a messenger boy for the “Chicago Examiner” newspaper. His shift was from 6:00 pm to 2:00 am.

The article from the Journal states that Sheriff was in the newspaper office one day when an editor saw a bulletin that a young man from Chicago had won a scholarship to Yale. When asked, “who is Arthur N. Sheriff?” the future headmaster replied, “that is I.” Sheriff then asked for a few minutes off so he could go home to tell his mother the news.

Moving to New Haven in 1909, Sheriff enrolled at Yale University and in 1913, he received a bachelor’s degree in education. A master’s degree in English followed in 1915. While at Yale, he tutored students at what he called the “Roxbury Apartment” on College Street. The name was to become synonymous with the Academy.

In a 1966 interview with the “Sunday Republican Magazine,” Sheriff said it was while tutoring at Roxbury that he first heard of the boys school in Cheshire. When he graduated in 1915, Sheriff joined the Academy as an English, chemistry, and physics teacher.

Some of the tutors from the Roxbury group affiliated with Yale formed a for-profit organization in 1917 and changed the Academy’s name to The Roxbury School (sometimes called the Roxbury Tutoring School). It began operating as a college preparatory school for Yale and other leading institutions.

Only 36 years old when he was named headmaster in 1922, Sheriff said in the magazine interview that the first years were not easy. “I traveled all over the country interviewing parents and enrolling students. Cheshire was a tiny village when I arrived. You had to take a trolley to get to Waterbury or New Haven and there were only a few buildings on campus,” he said. The atmosphere created by the faculty allowed for “a flexible curriculum, small group instruction,” Sheriff noted in the interview. His quote that. “education by contact of personality, and painstaking encouragement for the individual potentialities of each boy,” describes the emerging model of a student-centered education that is the core of the Academy’s mission today.

Just four years into Sheriff ’s tenure, Arthur S. Wolff enrolled at the Academy. Wolff was the father of two famous writers, Tobias and Geoffrey Wolff, both who wrote biographies about their childhoods. The 1979 book, The Duke of Deception, written by Geoffrey Wolff mentions the “venerated headmaster” at Roxbury School. A passage notes that Sheriff wrote to Wolff ’s father about his son, noting Arthur, “has not studied, but now means to get to work.” Despite Wolff ’s dwindling grades, Sheriff was still optimistic about the student’s abilities.

“Arthur’s instructors, in general, report that he has a good mind, woefully lacking in training. His understanding of original thought are good ... I have found also that the mistakes he has are due more to thoughtlessness than to premeditation.” Arthur Wolff did graduate from Roxbury School in 1928 and was accepted to the University of Miami.

The building blocks of a student-centered education are evident as early as 1928 when Sheriff wrote an article in the “Roxbury Record” that the school should focus on “the development of character—self reliance, self knowledge, self respect; a willingness to work to win and an unwillingness to win meanly.” In an early 1930s essay from the “The Academy Review” entitled, “The Headmaster Explains Cheshire Educational Policy,” Sheriff enumerates key points of his educational model:

- Flexibility of organization

- Opportunity for self expression

- Healthful activity

- Persistent discipline

- Friendship between teacher and student

By the 1930s, Sheriff ’s philosophy of teaching was reaching far beyond the Northeast. An article in the Greensboro [South Carolina] Record highlighted the headmaster’s insight. “The modern boy does not assume a pose because he thinks it is the right thing to do. He lacks the sheep-like quality of former generations and has more independence, less hypocrisy, and more real honesty.”

HE WAS A PEOPLE PERSON AND A FRIEND. HE WOULD SEE YOU STRUGGLING AND HE’D HELP YOU.

- LOU RICCIUTI ’52

REMARKABLE HUMAN BEING

A major change at the Academy came in 1937 when the school received a new charter from the state legislature. It was allowed to revert back to a non-profit entity and the name was changed to Cheshire Academy. As part of the charter, the school was required to provide four, one-year scholarships annually to a Cheshire resident. So began the “Town Scholar Program,” which was later altered to provide one, four-year scholarship annually. Presently, partial scholarships are also awarded.

In the late 1940s, Sheriff allowed returning WWII soldiers to finish their high school education utilizing the GI Bill. Horton Hall was donated to the school by the government as housing for returning soldiers. Under an accelerated program, which lasted until the early 1950s, a number of former soldiers studied at the Academy. Many classes had students ranging in age from 16 to 23 years old.

Lou Ricciuti ’52, whose family co-owned the Waverly Inn on Maple Avenue for about 50 years, remembers how kind Sheriff was to students. “He knew what you were trying to accomplish and he would help you academically with guidance,” Ricciuti said. “He was a people person and a friend. He would see you struggling and he’d help you.” Sheriff enjoyed dining at the Waverly Inn and arranged for the restaurant to stay open late on prom nights, Ricciuti said. “So the students wouldn’t get in trouble; they had a safe place to go.”

Thomas J. Dodd Jr. ’53, a former U.S Ambassador to Uruguay and Costa Rica, remembers Sheriff as a “remarkable human being.” In a 2001 interview with the Association for Diplomatic Studies and Training, Dodd said his interest in Latin America began at the Academy when he was assigned a roommate from Cuba. Neither student spoke the other’s language at first, he said, but within a few months, they were conversing easily.

Current events were discussed at weekend gatherings at Sheriff ’s House on the church green. The “headmaster was always interested in international affairs ... He always seemed to create an environment with a lot of students from abroad, from all over the world,” Dodd said. Former U.S. Sen. Christopher Dodd, of Connecticut, Thomas’ brother, entered a proclamation into the Congressional Record in 1994, to commemorate the bicentennial of Cheshire Academy. Mentioning Sheriff in the document, Christopher Dodd said the school “has never lost its dedication to excellence in education. But it is important to remember that the school’s mission is not only to educate men and women of Connecticut, but also to instill in them a sense of personal worth and character.”

A University of Connecticut professor, Albert E. Waigh, was the 1958 commencement speaker at the Academy. In his personal journal entry from that day, Waigh mentioned his meeting with Sheriff in the headmaster’s office in Bowden Hall. “It is a pleasant, long, narrow office … with a fireplace and many chairs and bookcases.” Waigh had lunch with Sheriff and then attended a garden party at the headmaster’s home on the church green before returning to Bowden Hall. “I found [Sheriff ] interesting. He has had one or two operations and seems to me rather weak, but mentally he is very alert,” Waigh wrote.

In 1966, Sheriff began letting colleagues know that he planned to retire. In a letter from November of that year, he wrote “I have seen the campus evolve through many stages from what to begin with in 1917 could be termed a small tutorial camp to the school of today, with a larger student body, although continuing to concentrate on close attention to all boys in small classes.”

During Sheriff ’s tenure, the Academy built Bailey Hall, the Alumni Memorial Building, the Alumni Auditorium (at the former south campus at the current Watch Factory Shoppes), Hurley Hall, the Richmond Infirmary, and Von der Porten Hall.

Despite having decades during which he could have given the commencement address, Sheriff waited until 1966, the year he retired as headmaster, to be the keynote speaker. He delivered the speech in the newly finished Arthur Sheriff Field House which was built to honor him.

An excerpt from that address sums up his 52 years at the Academy and his path to retirement. “Memories we shall carry with us wherever our destinies may bring us—and I know from my experience with thousands of alumni that this may be far and distant in time. We may not always be aware that these memories are with and us and as great a part of us. But often we are reminded. A brief glimpse of an almost forgotten scene, a face in a crowd in a distant place, the sound of music in the air, the touch of another’s words, will again enliven the past and you will again return for a brief, but happy few minutes to a scene you will never forget.”

STUDENT-CENTERED EDUCATIONAL MODEL

1. FLEXIBILITY OF ORGANIZATION

2. OPPORTUNITY FOR SELF-EXPRESSION

3. HEALTHFUL ACTIVITY

4. PERSISTENT DISCIPLINE

5. FRIENDSHIP BETWEEN TEACHER AND STUDENT