The headmasters and I stood on the track as rivaling JV boys soccer teams dribbled their way down the field. At 10:30 a.m., the stands behind us were filled with colorful team paraphernalia and excited cheers. I invited Joe Seivold of Berkeley Preparatory School and Kevin Plummer of Tampa Preparatory School to speak with me for roughly ten minutes about the ongoing Headmaster’s Challenge. The following is a transcription of our conversation after introductions and greetings.

ME: When did the Headmaster’s Challenge come into existence?

PLUMMER: We’re 4-10 and 1… so this is the 16th… so 2004. This is the 16th Headmaster’s Challenge.

ME: Who’s idea was it?

SEIVOLD: So it was begun by the two headmasters of our schools prior to our arrival.

ME: Who were they?

PLUMMER: Mr. Merluzzi at Berkeley Prep and Mr. MacLeod at Tampa Prep.

ME: What sports were played at the first Headmaster’s? Were they the same?

PLUMMER: Every one of them. The history of it says that there were 16 sports that were played… but we don’t actually have 16 winter sports, so it’s the exact same model that we have today.

SEIVOLD: So all the winter sports.

PLUMMER: It was modeled after the rivalry of Deerfield and Choate, that they have up in New England. When you go up north, they have a bunch of schools that have *this* coined moment where they play all of the schools. Each school plays all of the sports that the given season offers.

ME: Personally, what’s each of your favorite sports to watch here at Headmaster’s Challenge?

SEIVOLD: I enjoy all of them. I enjoy from the moment I get here until the moment the event ends. It’s so great to watch our students competing and I enjoy all the sports—I mean, they’re great spectator sports. But it’s most fun to watch our kids in competition. You know, these kids you see all day long, walking around the halls, and they’re really going after it here on the fields, and the courts and the mats. It’s a moment of great pride for me, for sure.

PLUMMER: I would agree with that. I really enjoy the sub-varsity level because for those students, to be able to have a crowd of this type for JV boys soccer… I’m not sure JV boys soccer ever has a crowd like this. I would say the same for middle school girls soccer and, you know, there’s a lot of great spirit, people there. You know the varsity teams get big crowds all the time, but all of the sub-varsity, middle school, they’re going to be seen by a lot of people.

ME: If you two had to compete in one of these events…

SEIVOLD: I’ll take him in soccer!

PLUMMER: I would probably pick basketball!

ME: In a wrestling match between the two of you?

PLUMMER: Someone asked us that this morning. I was like, are you kidding me? Look at the two of us together! We’re NEVER getting on that mat!

ME: Are you both familiar with Hemingway’s six-word-stories?

SEIVOLD: Yes.

PLUMMER: Remind me.

ME: So basically, a six-word story is when you take six words to describe a whole big picture. For example: Once worn shoes used no more. So, what I’m going to ask you to do, is come up with a six-word story that embodies your entire school.

PLUMMER: For this day?

ME: I would just say in general.

SEIVOLD: Really? On the spot like this? (A brief pause, the race to come up with the perfect six-word story creates competitive tension between the two men.) Spirited community making positive difference daily!

ME: I love it! You win!

SEIVOLD: That’s a point!

PLUMMER: We came, we worked, we loved!

ME: Aw, that’s awesome too! You’re both very sentimental.

PLUMMER: I take it you’re a senior? (At this point, all of a sudden, I was being interviewed.)

ME: No, I’m actually a junior.

PLUMMER: One more year to go.

ME: One more year.

SEIVOLD: Don’t be in a hurry, Tess.

ME: I’m not, I like it here. Final question: If you could take any class, or join any club at your school, right now, which class or club would you like to be a part of?

SEIVOLD: See, you’re asking us to pick favorites, that’s a tough deal for us.

ME: It’s not picking favorites! It’s playing on your personal skills, you know? You communicate well, I could see you both being debaters…

SEIVOLD: Well, because it’s not possible anyway, I’m going to say Martha DeWeese’s Microbiology. It is infamous for being the most challenging, most interesting and most transformational class for so many people, so many hundreds of our alums. I could never handle that class, I don’t think, but you’re giving me a hypothetical so.

PLUMMER: I’m going to have to go with Doug Smith’s AP U.S. history. It’s infamous at our school for being very very difficult, very very bulky, but highly an enjoyable class. Mr. Smith is just a beloved teacher, so I probably would have to go just to see what the legend of AP U.S. is all about.

After we said our goodbyes, I returned to my place in the stands, alongside my friends. As I watched JV boys soccer, I caught the two headmaster’s standing next to each other, laughing, out of the corner of my eye.

The real Headmaster’s Challenge: Allow competition to bring you closer to the people around you.