Prep Talk
Rooted in Richland: Kenny Pressley’s Journey of Faith, Family, and the Prep Community
Posted November 5th, 2024
Welcome to “Rooted in Richland,” a series highlighting the people who truly make St. Augustine Prep such a special place. Through this series, we aim to share the stories of members of the Prep Community who embody the Augustinian values of Veritas, Unitas, and Caritas—Truth, Unity, and Love. From alumni and students to faculty, staff, and friends of the Prep who have built the school’s legacy from its early days in 1959 to today, these stories will express how our shared mission has shaped the lives of many and strengthened their Augustinian roots.
We are honored to begin this journey with Kenny Pressley, a cherished member of our Facilities team. Mr. Pressley’s story is a testament to how faith, love, and community thrive throughout our campus, reflecting the very essence of what it means to be “Rooted in Richland.”
Mr. Pressley has become an integral part of St. Augustine Prep. Each morning, students greet him warmly, and their joy always fills him with gratitude to start the day. Coming out of retirement to join the Prep family, “Mr. Kenny” — as he is affectionately known to all — has found a renewed sense of purpose and belonging among our students, faculty, and staff. Reflecting on the deep admiration he holds for the Hermit Brotherhood and the school itself, he mentions, “I see every student here as already being successful, simply for balancing their days at a school as rigorous as the Prep.”
Mr. and Mrs. Kenny and Maxine Pressley pose for a quick photo before making the trip to the Prep for Convocation.
Before joining St. Augustine Prep, Mr. Kenny served as the Supervisor of Facilities and Grounds for the Stratford School District. His experience, expertise, and dedication are evident in every corner of our campus, but it’s his unwavering faith and love for God that truly sets him apart. A devoted husband to his wife, Maxine, and the proud father of two sons and two daughters, Mr. Kenny’s life is a testament to the power of a loving family. His appreciation for his beloved Maxine, whom he credits as a daily reminder of God’s love, is central to his story. His wife’s support and insight have always been a source of strength, especially as she’s witnessed first-hand the transformation the Prep community has brought to Mr. Kenny’s life. During a conversation at the dinner table in the Pressley home, Maxine lovingly remarked to her husband, “Your walk is different, your talk is different.” Her observation captured the profound effect the kindness of the students and the Prep experience has had on him.
Mr. Kenny’s gratitude extends to the entire Prep community, which welcomed him with open arms. He fondly recalls how he was provided the opportunity to publicly express his gratitude serving as a guest speaker during Convocation. The special day allowed him to openly acknowledge the warmth and support he’s felt since his first day in Richland. For Mr. Kenny, his Prep family embodies the Augustinian value of caritas, the selfless love of seeing the face of God in others — a cornerstone of the Augustinian mission of the school.
Kenny takes a moment with Max Watson (Left) and Noah Plenn (Right) before last year’s Commencement ceremony.
He personally holds dear three core ideals: live with purpose through God, trust in His guidance, and never be afraid to ask for His help. These principles have shaped his daily interactions, whether he’s sharing a kind word with a student-turned-alumnus like Max Watson ’24, who made it a point to check in with him every day, or offering a listening ear to any student in need. Mr. Kenny finds immense joy in witnessing the mutual respect and care between students and teachers, a dynamic he believes is the magic behind the school’s tradition of success in developing Christian Gentlemen and building everlasting relationships.
Mr. Kenny’s story is a powerful reminder of the transformative nature of faith and the Augustinian emphasis on building a community. His journey at St. Augustine Prep is a living testament to the values that shape our mission. “Let God into your lives and allow Him to help you,” he advises, underscoring the importance of gratitude and trusting in God’s plan.
Mrs. McHugh, Dean of Academics, poses for a photo with Mr. Kenny who donned a Prep blazer for his convocation address.
Maxine, also sharing her perspective, beautifully captured this sentiment when addressing students: “I am very grateful to see the reciprocation of God’s love through Mr. Kenny and through all of you, the students and faculty and staff of St. Augustine Prep. Gratitude is something special, as we sometimes take things for granted. You all have a long way to go in life, so much to see and experience, so many challenges, but always remember, if you keep God at the center of your heart, and allow Him to direct your path, you will be successful. Don’t ever give up on your dreams and be grateful for everything that comes your way.”
Mr. Kenny’s presence at the Prep and the caring heart of his wife have not only uplifted him but have also profoundly impacted those around him. His story is foundational for the “Rooted in Richland” series, reminding us all that every member of our proud community, from faculty to staff to students, all play a vital role in living out our shared mission and impacting the lives of our Hermits.
Through Mr. Kenny’s example and Truth, Unity, and Love, we are all “Rooted in Richland.”