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17 Years at Holy Trinity School

By Declan Leonard


That all three of our kids went to Holy Trinity School started out as an afterthought. It was the early 2000s, and we were having second thoughts about the language immersion program at our local elementary school. On a whim we attended a Holy Trinity School Open House, having been parishioners of the Parish for many years prior. I still vividly remember sitting in what was then the Holy Trinity Theater, as we listened to a presentation about an elementary school that would become a school home for our family of three kids for the next 17 years.

As a parent, my first real interaction with Holy Trinity School was the annual Trivia Night the year our oldest daughter was in kindergarten, nearly a decade and a half ago. Back then, the school grounds were so limited at Holy Trinity that we had to borrow space at nearby Blessed Sacrament to accommodate what was consistently a large turnout of enthusiastic school parents. The parents we met that night, bonding over kegs of beer and paying “bribes” for trivia clues, would become life-long friends. Our unbeatable team, appropriately nicknamed “Dynasty” and equipped less with brains and more with checkbooks, would go on to dominate many Trivia Nights thereafter.

The first time I heard the Holy Trinity Jesuit school motto “children for others” I wasn’t entirely clear what that meant. I decided to get more involved with the parent association at the school, and soon I was charged with helping to organize service projects for the kids and school families. As a Jesuit school, Holy Trinity has always had a very rich tradition of giving back to the community, so I had large shoes to fill in this new role. We decided as a group that the best way to instill charity in kids was with hands-on work, and from that was born the annual Gleaning Project in which school kids and parents work on a nearby farm harvesting crops to be donated to local food banks. I still remember one of the earliest gleaning projects watching car after car with “HTS” magnets pull onto the fields of Miller Farms in Maryland, where over a hundred members of the Holy Trinity School community worked together to clear the field of vegetables to feed the needy in our area.

As my oldest daughter graduated from Holy Trinity School and went to high school down the street, the temptation was there for me to dial it back and step aside from any formal parent role at the school while my middle son made his way through. But somehow-and I am sure drinks were involved I was egged on to head up the entire parent association for the school. I remember friends from outside Holy Trinity warning me that getting too close to any organization, let alone an elementary school, was a bad idea. What they didn’t realize was that at Holy Trinity School, we had a legend for a principal, Charlie Hennessy, who made my relatively limited role that year a piece of cake. I was privileged that year to witness first-hand how parents, teachers, and administrators can work together to make a school experience worthy of our children.

What I have always found with Holy Trinity School is that, whatever we lack in space and amenities, we make up in community. Community is without a doubt the heart and soul of Holy Trinity School, much like it is with the Parish. When I attended a school Father’s Club BBQ event this past Fall, I realized with COVID that many of the more recent Holy Trinity School families have sadly been robbed of the opportunity to experience first-hand what a great and fun community that is Holy Trinity School. I really hope as time goes on that they get to see Holy Trinity School the way my family has experienced it—trivia nights, golf tourneys, galas, father/daughter dances, poker nights, beer…

Now I am down to my last few months of doing drop-off for my final child at Holy Trinity School. At what has long been an annual dinner gathering of some dads around Christmas Time at Fogo de Chao--these being many of the same dads I met at that first Holy Trinity School Trivia Night roughly fifteen years earlier--the talk turned to how things are going at the school these days. We realized that I was the only dad at the table who still had a kid at the school (and the only one whose hair wasn’t fully gray yet). I told them that as nice as our memories of the good old days might be, that in my experience in this final year as a school parent, with Kevin McShane now at the helm assisted by Charlie Hennessy and so many dedicated teachers and administrators, Holy Trinity School is as strong if not stronger than when our family entered it 17 years ago.3


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