Chesterton Wins Yass Prize, the “Pulitzer of Education”

March 25, 2026

Chesterton Academy of Orlando

We are excited to share that the Chesterton Schools Network (CSN) has been awarded the $1 million Yass Prize. Considered the Pulitzer Prize of education innovation, the Yass Prize is devoted to identifying and elevating the next generation of education change-makers.

The award recognizes our parent-powered model that enables communities nationwide to launch joyful, rigorous, and affordable classical high schools. You can read the press release here.

Even more excitedly, Chesterton Academy of Orlando was chosen as the feature location to receive this award! Watch the video below:

The Chesterton Schools Network was selected from a final group of 23 contenders—out of thousands of applicants—for its innovative model empowering parents as educational entrepreneurs to launch joyful, rigorous, and affordable classical high schools in their own communities.

The prize announcement also noted the Network’s rapid expansion to more than 70 Chesterton Academies currently and its proven model for restoring deep thinking, virtue formation, and joy to the high school experience.

The Chesterton Schools Network will use the $1M Yass Prize to expand capacity dramatically to meet surging demand from parents and families, driven by school choice and the CSN’s growing reputation as a leader in renewing Catholic education in our time.

On track to reach 150 schools by 2030, the CSN’s long-term vision is to serve 1,000 schools globally by 2040, with over 100,000 students. The Network’s leadership sees the Yass Prize funding as a crucial catalyst to achieving this goal.

Chesterton Academy of Orlando


Chesterton Academy of Orlando is a classical high school, grounded in the Catholic faith. Our mission is to help students recognize the true, imitate the good, and adore the beautiful, falling in love with the source of it all—God himself.

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