Archie Douglas, a previous headmaster of The Montgomery Academy, said in 2004 that he believed the school was started in reaction to desegregation and "that those who resented the civil rights movement or sought to get away from it took refuge in the academy." He noted that the school, by 2004, had a philosophy of openness and did not discriminate with regard to race. As of 2014, the student body of The Montgomery Academy is more than 10% percent non-white. In June 2020, during the protests that followed the killing of George Floyd, headmaster John McWilliams said, "We must be willing to confront the uncomfortable fact that The Montgomery Academy, like many other independent schools founded in the South during the late 1950s, was not immune to the divisive forces of racism that shaped this city and community over the course of its history".