By Andy Hutchison

WESTPORT — Two key contributors to the success of the Staples High football team this season are brothers who have been attending games and supporting the Wreckers since long before their high school playing days.

Caleb Smith (Class of 2024) and Nathan (2025) have helped the Wreckers to an 8-1 record and No. 3 spot in the Class LL State rankings heading into the annual Thanksgiving battle with Greenwich (on the road at 10 a.m. Thursday).

Caleb is the Wreckers’ quarterback, and in addition to being a captain of the football team, he is a captain of Staples basketball team and member of the lacrosse team. 

Caleb has received CIAC All-State recognition, as well as the following accolades: Walter Camp All-State Second Team, FCIAC Top 45, Walter Camp FCIAC Player of the Week in Week Three this fall.

Nathan is a wide receiver and also plays QB, safety and cornerback. He plays basketball along with his older brother and also plays baseball.

“What a blessing to watch our boys play for Staples after so many years rooting for the Wreckers as a family,” said Dave Smith, father of the Staples football siblings.

“As a family, we went to lots of Staples football games — support the local team. Thanksgiving morning at the game was a big deal for our family,” Dave added.

And in recent years the games have had extra meaning with the brothers on the field. What’s more, younger brother Noah is a ball boy for the Wreckers.

The varsity Smith athletes played football together in first and second grades for the PAL Flag football team. Their dad was coach. Due to the youth program going year by year. the siblings did not reunite on the gridiron until high school.

They have opposed one another only once, in Westport Little League fall baseball when Caleb was 12 and Nathan 11. They pitched against each other.

They have worked well together on the football field, connecting for touchdown pass plays, helping the Wreckers pile up wins as they eye state playoff success.

Following is a Q&A with the Smith siblings

How much fun is it playing with your brother?

Caleb: It’s a dream come true. After all of the years of playing in the backyard and watching the Staples High games when I was younger — actually being on the field and throwing passes to Nathan has been really special and I am very thankful for the opportunit.

Nathan: It’s a lot of fun. And even better since he is the best quarterback in the state. We have both dreamed for times like these and it’s amazing that it is all coming true. 

What is the hardest part? do you push each other to do better?

Caleb: As a leader, I feel as if my responsibility is to push my teammates, including Nathan. However, I think Nathan does get pushed harder than others just because he is my brother and I have high expectations for him. 

Nathan: Caleb is a great leader and he’s not going to go easy on anyone. He does this to make the team better as a whole. As much as Caleb pushes me to be the best version of myself, I try to do the same for him.

What do you like about football in general?

Caleb: Being a part of a team of my friends that I have been close with my entire life. There are pictures of me and multiple teammates playing football together from back in first and second grade. The fact that this game can give me friends for life is why I love it so much.

Nathan: Football is the ultimate team sport. It’s impossible for any one player to win by themselves. It takes the whole team to be successful. It takes a lot of trust with your teammates which is what I love about football. Working so hard all year helps make close friendships between everyone on the team that last a long time.

Plans for college?

Caleb: Planning to play football in college — likely study business at school.

Nathan: I plan to play football in college and to study business.

Best memory from your days at Staples thus far, and/or best youth football memories?

Caleb: Beating Greenwich last year on Thanksgiving was a special game for me. With such a big crowd and coming back from behind. A game I will never forget.

Nathan: My first touchdown catch against Ridgefield in Week Two. It was so special for me because after having a rough Week One, the team bounced back and had a statement win against Ridgefield. And it was Caleb and my first touchdown connection of the year. I will never forget the feeling I had the moment I stood up and celebrated with my team and Caleb.

Andy Hutchison has been covering school sports — including Staples athletics — as well as news and feature stories in Fairfield County, since the 1990s. Learn more about us here.