Kent was one of the first schools to provide tuition discounts based on what a family could afford to pay.

The school's list of notable alumni includes philosopher John Rawls, Secretary of State Cyrus Vance, and three winners of the Pulitzer Prize.

Kent School was founded by Anglo-Catholic Episcopal priest Frederick Herbert Sill in 1906.

[1][2] It arrived at the tail end of the wave of British-style boarding schools set up at the turn of the twentieth century.

[3] Sill admired England and wanted to spread English influence within the United States.

[1][5] Sill realized that many of his students would have to come "from families of moderate means who could not afford the tuition fees at the then established boarding schools of the [Episcopal] Church.

[1][21] Following Kent's 1943 disassociation from the Order of the Holy Cross, the school retained its broader affiliation with the Episcopal Church.

However, the apartheid-era South African government refused to grant the student a passport, causing an international incident.

[29][30] When Kent began admitting girls, it dropped the sliding-scale tuition model and shifted to a more conventional financial aid system.

[31] Schell improved Kent's financial position by raising a large endowment, which stood at $87 million in 2017.

He was previously Kent's assistant director of admissions in the 1990s, and most recently served as rector of St. Paul's School in New Hampshire.

[41] Kent follows a trimester system in which a school year is fall, winter, and spring terms.

Kent competed for the Thames Challenge Cup in 1933 with the support of President Franklin D. Roosevelt who sent a letter to Sill offering his "good wishes for a successful trip" and commenting on how "the presence of a crew of American school boys will be helpful in strengthening the ties between good sportsmen of the two countries.

The Times in Britain wrote, "Kent School were almost certainly the best crew that ever rowed in the Thames Cup.

In 2010, Kent Boys Crew won the New England points trophy and placed 1st at Youth Nationals.

The team traveled to Henley and were the runners-up for the Princess Elizabeth Cup, losing to Eton College.

[53] Reportedly, Schell helped persuade companies like Coca-Cola, Philip Morris, KFC, and Sprint to withdraw their advertising from the show.

[55] To commemorate the occasion, the school commissioned a Kent student to create a video in which MacFarlane's friends and family recounted episodes from his childhood.

The reporters noted faculty alleged as abusers being relocated to different schools, including Kent.