DURING HIS formative years in Maryland, Kasey Kesselring’s mother and three siblings gathered around the dinner table each evening, taking turns reading from the devotional “Our Daily Bread.” Despite being a promising athlete who did well in public school, Kesselring’s older brother struggled with reading.
“My siblings would often volunteer to do the reading because it would take too long and cut into our time to go outside and play with the neighborhood children,” recalled Kesselring. “My father was a military colonel and ranger in the U.S. Army, so he was gone during most of my childhood. We lived in a rural community that happened to be a few short miles from Saint James School, a small Episcopal boarding school founded in 1842. Our first acquaintance with the school came by way of George Shank.”
Shank was the caretaker for Saint James but moonlighted as a house painter.
“My mother hired George to paint the exterior of our farmhouse. At his urging, she took on the responsibility of washing and ironing the laundry for the priest/ headmaster as a way of supporting the family finances. Once a week, George would show up at the back door to drop off and pick up the laundry. During these colorful interactions, he encouraged my mother to consider sending my brother to Saint James School.”
With the help of a financial aid program and their parents’ willing sacrifice, Kesselring’s brother enrolled, and four years later, so did he.

“Latin was a requirement for all eighth graders, but in the ninth grade, you could choose to transition to French or Spanish. I continued studying Latin and, upon entering college, continued to study Latin and Greek with a double major in music. This experience at Saint James shaped me as a person, developed my faith, and further inspired me to be a part of such a special experience.”
In order to provide a “well-rounded” childhood, Kesselring’s parents required each of their children to play a musical instrument. Kesselring chose piano, but he also began playing the saxophone and tuba and sang in the church and school choir.
“I continue to be a strong advocate for music in schools, and I completed my doctoral dissertation studying the effects of music in the classroom setting and specifically using music as a learning technique. Setting learning information to familiar tunes in elementary classrooms increased performance scores exponentially as compared with those who learned through traditional memorization techniques.”
His junior year of college, Kesselring returned to Saint James School, but this time he wasn’t a student.
“I had the opportunity to complete an internship program. That experience further solidified my interest and passion to continue in education.”
After earning a bachelor’s degree in classical languages and music from Dickinson College, he accepted the position of director of college counseling and assistant director of development at Saint James School.

In 1993, he married his wife, Maureen, who is also an educator, and they moved to Bell Buckle, where Kesselring served as the assistant head of school at The Webb School until 1999. During this time, he earned a master’s in education from Middle Tennessee State University in administration and supervision. They moved to Orlando, Florida, so that he could serve as the president of Montverde Academy. Under his leadership, enrollment swelled from 103 students to over 1,400, and the school completed $90 million in capital improvements and renovations. He also completed his doctorate in educational leadership from California Coast University and completed a post-doctoral certificate in management and leadership from Harvard Business School and Harvard School of Education.
In 2001, Kesselring received the unsettling news of a cancer diagnosis, but he didn’t allow that to stifle his passion for learning or volunteering within his community.
“This experience gave me a window of understanding into the needs and demands of health care, which led to several rewarding experiences. I was fortunate to serve as chairman during the transition and sale of Orlando Health and helped establish the Live Well Foundation with $150 million in assets to support health and wellness initiatives in Central Florida.”
After moving back to Wartrace, Dr. Kesselring completed a project for a health care community in Manchester and was later recruited to First National Bank of Middle Tennessee as the vice president.
Kesselring’s journey is a testament to the transformative power of education, the impact of dedicated mentors, and the enduring influence of family values and faith. His legacy continues to inspire and shape the lives of those he serves. GN