Lessons from the Underdog

These remarks were shared at the Opening Belltower Ceremony on August 26, 2026.

Good morning everyone, and welcome to start of the year! When I was a young boy, one of my favorite TV shows was Underdog. The main character was a dog who worked as a shoeshiner. He was humble and lovable, and like Superman, when danger was near, he would transform to become a flying caped-crusading canine hero called Underdog. When he flew into danger, he would announce himself by saying, “There’s no need to fear, underdog is here.”

We often celebrate the underdog: the person or people who, despite all evidence to the contrary, are able to rise up and confront life’s challenges. We cheer for the underdogs whether or not they actually win the game, and if they do, we cheer even louder. That’s what happened this summer when I watched the soccer team from my family’s home country of Cape Verde, play in its first-ever World Cup. If you have never heard of Cape Verde, you are not alone; most of the world didn't either, until this summer. Cabo Verde is an archipelago of ten small islands off the coast of West Africa with a very small population. When this underdog team qualified for the World Cup, the government gave the country the day off to watch their first game.

Nobody expected much from Cape Verde. They were ranked near the bottom. The players played for small soccer clubs most fans had never heard of. In the first game they shocked everyone by tying against Spain, the European champions. They then tied Uruguay, a team that has won the World Cup twice. Then they tied against Saudi Arabia. Three games, unbeaten, and Cape Verde, remarkably advanced to the final 32 teams to play against the defending champions, Argentina and Lionel Messi. 

Cape Verde didn't win the tournament. They didn't even win that game. But nobody in Cape Verde remembers this summer as a loss. Here's what I learned watching Cape Verde this summer, and what I hope we can take with us this year.

First, being underestimated is not the same as being unprepared. Nobody handed this team anything. They earned every draw with discipline, with trust in each other, and with the kind of preparation nobody saw on TV. This year, some of you will walk into a class, a tryout, a stage, or a friendship being underestimated, maybe feeling like the smallest one in the room. That is just a feeling, it doesn’t get to define your story. Believe in what you bring to the table as the amazing wonderful person that you are, just as you are.

Second, a team of disparate, diverse people only works if everyone shows up for one another. Cape Verde’s players came from clubs scattered across Europe and Africa. They barely trained together at all. What made them a team was showing up for one another when it mattered. This school, from our youngest preK aardvarks all the way up to our seniors, is also scattered: different buildings, different schedules, different lives outside this campus. And yet, that diversity of perspective and experience can be our strength, uniting us as a team when we intentionally show up for each other in an inclusive and beloved community.

Third, winning is not the point: a draw actually can be a triumph, and a loss can be a beginning. Cape Verde didn't win any trophies this summer. But an entire nation of children now believes something they didn't believe back in May: that they could hold their own with the best; that they belong. I spoke with my 90 year-old godmother and my relatives after the World Cup this summer. All of us felt such pride. For the first time in our lives, we didn’t have to explain to others where we were from. The underdog helped us to see and be seen – not because they won the scoreboard, but because they won people’s hearts.

So, my hope in this 157th year of OES, is that every one of us, in Lower School, Middle School, Upper School, faculty or staff, parents, and friends, embraces the virtues of the underdog. This year, live from the truth of yourself, not based on others’ expectations. Be a team and show up for each other. Play with compassion and heart, and use your power for good. Then in this place, this year, there will be no need to fear: underdog is here!