Headmaster of Conn. prep school placed on leave amid IRS probe

By the Editorial Team · Sunday, October 25, 2026

Suffield Academy’s headmaster, Charlie Cahn, has been placed on leave amid an undisclosed IRS investigation. The school plans to have Jennifer Bobo succeed him as head of school in July 2027, following his announced departure two years prior.

The headmaster of Suffield Academy in Connecticut has been placed on leave amid an ongoing Internal Revenue Service (IRS) investigation, according to sources familiar with the matter. Authorities have not publicly confirmed details of the investigation.

Charlie Cahn, who has led the prestigious prep school since 2001, was the highest-paid staff member in 2024, receiving more than $1.3 million in total compensation as reported in the school’s most recent tax filings. Earlier this year, Cahn announced plans to step down from his position in June 2026.

Cahn’s leadership at Suffield Academy spans more than two decades. During his tenure, he and his wife, Hillary—an alumna and former head of the school’s alpine ski program—established the Cahn Scholars Fund, a financial aid initiative that has contributed to the school’s growing endowment. In September, the academy reported that donations to the fund helped push its endowment beyond $100 million. The couple was honored at a campus event on October 16, marking the conclusion of their 23 years of service.

Before becoming headmaster, Cahn joined Suffield as an English teacher and lacrosse coach. He later served as faculty dean and admissions director. Throughout his career, he traveled extensively to promote the school, including visits to Seoul, Shanghai, and Hong Kong, according to the academy’s public communications.

Suffield Academy, founded in 1833 originally as a Baptist seminary, today operates as a secular institution. It enrolls approximately 420 students across grades 9 through 12 and offers postgraduate studies.

The school announced that Jennifer Bobo, who joined the faculty this year, will succeed Cahn as head of school effective July 1, 2027. Bobo’s late husband, Michael, raised their three sons in North Andover; one of them, Jake Bobo, currently plays professional football for the Seattle Seahawks.

The IRS has not provided comment on the investigation, and no public records currently indicate the specifics or scope of the inquiry involving Cahn. The academy has not released a formal statement regarding the matter.

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