Charlie Cahn III, the longtime head of Suffield Academy, was reported missing the day before the Connecticut boarding school announced on Oct. 22 that it had placed him on leave over an IRS investigation into him. Police had searched the academy's property looking for him but did not find him there.
According to The Boston Globe, Cahn's disappearance and sudden leave capped a dramatic turn for a man who had led the 350-acre campus near the Connecticut River for 22 years. Suffield Academy, which has operated for nearly two centuries and enrolls about 420 students — roughly two-thirds boarders and about one-fifth from abroad — announced his leave that same day, with board chairman Frederic B. Powers III signing the original statement. Suffield charges $79,400 in annual tuition for boarding students, according to facts compiled from the Boston.com report by Mike Damiano.
A Rapid Fall for a Towering Campus Figure
Cahn joined Suffield in his 20s as an English teacher and lacrosse coach before rising to head of admissions and dean of faculty, then became head of school in 2004 at age 34. He was regarded as a transformational figure at the academy, where he and his wife, Hillary Rockwell — herself a Suffield teacher and ski team coach who was raised on the campus — raised their two children, who also attended the school. The couple helped select recipients for the Cahn Scholars Fund, a scholarship program for lower-income students that the school said would carry on the Cahn family's legacy beyond his planned retirement.
Cahn's compensation placed him among the highest-paid boarding school leaders in New England. A 2014 ranking based on IRS 990 filings listed him third among the region's highest-paid heads, at $664,679, trailing Tabor Academy's headmaster, who topped the list at $822,011, according to Boston.com's 2014 analysis, which also found the average pay among the 50 highest-paid heads exceeded $420,000 annually that year. By 2020 through 2024, his total compensation exceeded $1 million every year — more than double his 2014 level, according to the school's tax returns — after the Suffield board approved a retention agreement that increased his pay. The New York Times reported that figure placed him at the top of the prep school pay scale.
Endowment Growth and a Namesake Chair
Suffield's endowment surpassed $100 million last year, doubling in value over the preceding six years. Daniel R. Tisch said growing the endowment had been a central focus for both Cahn and the board during that stretch. The school invested $120 million in construction and renovations during his tenure, according to the Globe, and created the Charles Cahn III Head of School Chair endowment, which Suffield said was meant to honor his historic impact.
Cahn had announced in 2025 that he planned to retire at the end of the 2026-2027 school year, and trustees named Casey Bobo as his successor that December, with her term set to begin July 1, 2027. Bobo assumed the head of school's day-to-day responsibilities once Cahn went on leave, Patch reported. She emailed the school community on Oct. 27 without mentioning Cahn or the investigation into him, according to the facts compiled for this report. Shortly before the leave was announced, the school had hosted a celebration honoring Cahn during Parents' Weekend; one Suffield parent said graduates' families loved him. Cahn had also been scheduled to appear at alumni events in Seoul, Shanghai, Beijing, San Francisco, Boston and New York in the months ahead, traveling frequently for fundraising both domestically and abroad.
School Says It's Cooperating, Even as Questions Mount
Powers told the New York Times that Suffield was cooperating with investigators but did not have insight into the full scope or direction of the government's efforts. He said the school had separately retained outside counsel to investigate matters involving its leadership and finances, and that he could not comment further because it was a private matter. Suffield also hired a crisis public relations firm and declined to answer questions from the Globe.
Tracy O'Keefe said school officials told the board that the investigation concerned Cahn's personal finances rather than the school's, and that Suffield was cooperating with the IRS and providing information. Current and former board members said the school had assured them its own finances were not under investigation. The Globe reported that it could not independently confirm the details of the investigation, and it is not established what exactly the IRS is examining.
Cahn's China Events
Separately, the Globe reported that a Suffield board member resigned the month before its report, according to school spokesperson Amy Randall. Cahn had headlined at least half a dozen events in China beginning in 2018; Shanghai and Hong Kong were among the locations of events in 2024 and 2025.
