Since the Great ’58’s 65th reunion, about 30 of the class have enjoyed comradeship through Zoom gatherings three to four times a year. Each of these sessions has been attended by 18-20 classmates, plus occasional wives who have been called in to assist non-technical mates. The prime objective has always been what Jim Guest describes as a “community of classmates….learning something new and experiencing fascinating exchanges,” with time for each participant to share personal news, books recommended, and travels undertaken.
On October 29, 2025, at Brian Rosborough’s initiative, we broke the pattern with a lively face-to-face Zoom interview with Dr. John Austin, Head of School. The hour was divided into thirds: we interviewed Austin, he questioned us, and then the class had time for their questions.
Brian Rosborough led off: “Should Deerfield be preparing students for life or for college admissions? Should we offer a more practicable curriculum?”
Austin explored what Deerfield strives to do in preparing students for life challenges as well as academic ones. Together, we explored how Deerfield might champion reading skills and reading comprehension to counter the AI effect of short-cutting reading in favor of AI algorithm-generated summaries and outlines to prepare for tests. Jim Guest challenged, “Does AI dramatically interfere with teaching and learning?” The Head responding: “It’s difficult……This is a Gutenberg-like moment. We’re in a post-literate screen age. A screen revolution. . .with individuals spending on average seven (7) hours a day on a screen. That’s about 25 years out of a lifetime. Community takes a hit. But we continue to emphasize deep reading and independent thinking.”
The second segment was the Head’s opportunity to ask the Class of ’58 a few questions. He led by asking, “What were the enduring lessons learned during your education at Deerfield. What had a lasting impact on your development?” Our answers included:
• Community: “The culture — classroom, athletics, listening to Mr. Boyden”
• Rigor: “Developing habits of thought”
• Family feeling: “Mr. Boyden made visits and even wrote us personal letters when he learned we weren’t doing well in college — having his driver take him to Amherst or Dartmouth or wherever close to give us a pep talk.”
• Determination: “Anything worth doing is worth doing right”
Sportsmanship: “After you knock them down, be sure you pick them up.”
• Structure: “I came from a hectic home. At Deerfield, I felt embraced, safe, structured.”
• Effort: “At our age, I’m more distracted, forgetful, and neglectful. When I don’t complete a household chore or a project I started, my wife invariably says, ‘Finish up strong, Jim.” That lasting impact lives on.
Dr. Austin’s time was abbreviated because our timekeeper, Peter Clark, moved the event to Part 3, the chance for classmates to ask questions of Dr. Austin. We explored topics related to technology (does it help or distract from learning), the COVID challenge (community is back), diversity (keep it going), and service activities (more farm work!).
Regarding today’s competitive secondary education world, George Carmany asked about the ‘value proposition’ of a school that charges $85K/year with only sixty (60) percent paying full boat. This was made palpable by the statistic Dr. Austin cited that “only 18 private schools out of hundreds are more than fifty percent endowment-income reliant.” Dr. Austin thanked the class for the lively exchange.
Following the program, the attendees expressed strong appreciation for the articulate leadership with which Dr. Austin is meeting the challenges of the 21st century.
• Bayley Silleck: “…by turns intellectually stimulating and powerfully moving as we all mentally compared our boyhood lives under the tutelage of the Quid and his great faculty to the modern and impressive school under Austin.”
• Bob Fernholz: “I was impressed by Austin’s focus and dedication to making Deerfield an extraordinary educational environment for every student. I was particularly struck — positively — by the no-cellphone policy.”
• Tiff Tiffany added: “….John Austin certainly sounds like the right person for these times for Deerfield. I credit Austin with courage to open the school in the fall of 2020 with national bewilderment pressing on whether to reopen schools, he was one of the few who ….did act on the instinct that there was no clear and present danger [from COVID] to students…..”
The twenty-four ’58 classmates attending were (in addition to those mentioned): Woody Chittick, Bill Cummings, Otto Doering, Tim Evers, Jerry Gibson, Bruce Grinnell, John Hayward, Roger Hoit, Spen Kellogg, Robin Mahar, Peter McCurrach, John Mendelson, Bob Murray, Warner North, Floyd Russell, Bill Webster, and Porter Wheeler.