Our School

Principal, Thomas J. Pompei was honored at the Catholic Academy of Waterbury's Annual Dinner with the Sisters of St. Francis Award. Prior to the awards dinner, Mr. Pompei's achievement was celebrated by the students and faculty at Holy Cross in a surprise school assembly. The Crusader community dressed up like their beloved Principal which included latex bald head caps. 

"We at Holy Cross have always known Thomas J. Pompei to be deserving of this award because of so many attributes," said President, Dr. Thomas C. Pellegrino. "(This includes) but not limited to his exceptional leadership of our classrooms and co-curricular experiences, his boundless energy and enthusiasm, his unwavering embrace of growth over achievement, his unconditional support of our exceptional teachers, his ceaseless attention to human relationships, his humility, selflessness, intelligence and huge heart." 

Watch below as Mr. Pompei gets his big surprise.

Mr. Pompei is a proud graduate of the Class of 1989 from Blessed Sacrament School and Parish. After nine wonderful years on Robinwood  Road, Tommy was accepted into the Class of 1993 at The Taft School where, in addition to his studies, he was a four-year member of the basketball and lacrosse teams, a two-year member of the soccer program, a four year member of United Cultures at Taft, and a member of Student Council. Tommy continued his education as a member of the Class of 1997 at Boston College as a student, a four-year member of the club/intramural basketball program, and a member of the BC Sexual Assault Crisis Network. He earned his BA in English Literature and Education.

After leaving Boston, Tommy moved to Dallas where he met his wife, Tracy, in 1998. They were married on September 30, 2000. They have shared 25 joyful years together between Dallas, Waterbury, and Oxford, and have been blessed with three outstanding children: Myles, Thomas Jr., and Layla. Both boys were educated at Blessed Sacrament School, and all three children have graduated/will graduate from Holy Cross High School. In addition, Myles and his wife, Alyssa, blessed the family with their first granddaughter, Paisley Pompei, in 2023.

After returning from Texas, Tommy earned his Master’s and Administrative degrees from the University of Bridgeport. He worked at Naugatuck High School for 18 years where he taught English for five years before he became an administrator serving as Dean of Students, Athletic Director, Assistant Principal, Director of Adult Education, and President of the Naugatuck Valley League.

In 2019, Tommy proudly became Principal at Holy Cross High School, the vocational position he had long desired in the place where he spent the majority of his high school years with his best friends, where he received his first teaching opportunity, and where he and Tracy sent all three of their children. He is honored to continue to serve the Holy Cross community in this capacity to date.

Through the years and experiences above, Tommy considers his greatest happiness to be the loving family and extraordinary friends with whom he has shared his life from his childhood on Terrell Road and the halls of Blessed Sacrament, to Boston, to Dallas, and back home again.