The property was sold by John McDonnell to Terry Leavey Lemons and Walter Ziglar, who soon converted the school to non-profit status.

He was also the chair of the first Board of Executive Directors, which included Bill Badham of Curtis School and Vern Simpson of Montclair Prep.

The school primarily employs its own teachers as coaches and requires that students maintain a certain degree of academic standing in order to participate in sports.

In 2003, Brentwood-area resident Arnold Schwarzenegger was the Guest of Honor and presided over the Special Olympics Games' Opening Ceremony.

In 2016, Brentwood School formalized its on-going relationship with a commitment to the VA valued at close to $1.8 million annually in rent and in-kind services.

On August 29, 2013, U.S. District Judge James Otero responding to a lawsuit by the ACLU, ruled that the West Los Angeles Veterans' Administration Enhanced Sharing Agreements that allowed VA land to be leased to Brentwood School, UCLA, and other businesses were not valid[5] As of the start of the 2014–2015 school year, the ruling that the VA must terminate those leases was under appeal to the 9th Circuit Court of Appeals.

[citation needed] The 22-acre athletic complex, built by Brentwood School on VA land, is a shared space known as the VCRE (Veterans Center for Recreation and Education).

In addition to being home to Brentwood School athletics, it offers extensive recreational, vocational, educational, and wellness opportunities to veterans and their families.