All College
Joseph Cunningham (’07)
Joseph Cunningham (’07)


Joseph Cunningham (’07) is the newly appointed academy director for Joseph of Cupertino Classical Academy (JCCA), a hybrid Catholic school in Orange County, California. 

In one sense, the appointment came as no surprise: Mr. Cunningham’s credentials include a thorough training in theology, extended experience in teaching, leadership roles in curriculum design, and over six years of work in financial management. Yet for Mr. Cunningham, the appointment is the latest step in an unforeseen journey which began many years before — with one small choice. 

In high school, a friend decided to attend Thomas Aquinas College’s High School Great Books Summer Program and suggested that they go together. Joseph took his advice and headed to California.

 “My time at TAC was providential. It was a time of study, but also of personal conversion — through the example of the tutors and priests, the kindness and mercy of the friends that I found, the education, and the sacramental life of the school.” 

It was a new world. He fell in love with the College and, after the close of the two-week program, eagerly looked forward to returning as a student. “I was an argumentative and inquisitive high schooler,” he recalls. “When I got to TAC, I finally found people who were willing to put up with my arguments.” But it wasn’t just the fun of matching wits with his fellow students that drew him back. The College had introduced him to the sacramental life in a way he had never known before, and the experience was a gentle call to revisit his view of education. 

Previously skeptical of Catholic schooling, Joseph became convinced of a vital relationship between learning and moral virtue. To him, coming to Thomas Aquinas College meant a recommitment to becoming a good Catholic man, and he decided to take the challenge. “My time at TAC was providential,” he reflects. “It was a time of study, but also of personal conversion — through the example of the tutors and priests, the kindness and mercy of the friends that I found, the education, and the sacramental life of the school.” 

All the while, he had no notion of one day being himself a leader in bringing such an education to others. “I never really thought about teaching,” he concedes. “I simply had this desire to learn, to pursue the truth. After the Summer Program I knew I needed to go back to TAC.” 

Over the course of his four years, however, he began to discern a special calling to theology. The work of St. Thomas Aquinas and St. Augustine held a special fascination for him, and as he explored and discussed their writings together with his classmates, he felt content. 

But that alone was not what drove him to pursue the subject further after college. “I would say that, most of all, falling in love with Jesus in the Eucharist really pushed me to seek Him more through continued study in theology,” says Mr. Cunningham. This search led him to earn a master’s degree in sacred theology at the International Theological Institute in Austria, after which he began his work as a teacher. 

“After school, when I got engaged, I decided that I needed to get a job, so I’d better become a teacher,” he laughs, “so it all came very naturally.” His first teaching job was with St. Francis Academy, a startup Catholic classical school dedicated to restoring the bond between faith and scholarship. 

Mr. Cunningham continued teaching for about seven years, until he discerned that God was calling him in a new direction: He took a position with the Knights of Columbus, and for the next six and a half years worked with insurance and financial planning for Catholic families. Looking back, he sees in this time the training he would later need to carry out his office as Academy Director. “In order for us to establish a strong Catholic classical learning community we have to be able to sustain it — to pay teachers, to handle the practical aspects of running the school, so that the beautiful work of education can be carried on. In other words, we have to combine the more practical side, business, together with the plan of education in order to be successful.”

Today, Mr. Cunningham directs JCCA in the midst of a growing movement of Catholic families returning to classical education. The school strives to combine the strengths of homeschooling and of traditional classes by introducing a partnership between parents and teachers. “What’s unique about Joseph of Cupertino is that it’s a hybrid model,” he explains. “Parents continue in their role as primary educators and stay involved in their children’s schooling, but at the same time have assistance from professional teachers to expand and deepen their instruction.”

As Mr. Cunningham sees it, the school’s mission is to provide both intellectual and moral formation: “The education we offer is really about helping them to become saints. For us at St. Joseph of Cupertino Classical Academy, that is the number one goal.” The structure of the program springs from a firm belief that “Catholic” and “academic” are not only non-contradictory, but also mutually dependent. 

To Mr. Cunningham, Joseph of Cupertino is a faithful response to a real need.  “You start to realize there’s a correlation between friendship with God and your ability to learn,” he says. “If we really are falling in love with the truth, then we have to live it. This was the challenge of TAC, and this was the great grace of God’s mercy to me — ultimately to be brought down that path and set up for success in my vocation as a result.”