
Photo by Danny Fulgencio.
Wen Anthony Benedetto first started coaching football at H. Grady Spruce, he had barely enough players to field a team. The squad went 1-9 his second season. But with hard work in the summer months, the team went 6-4 the following year and made the playoffs. “Coaches were hugging. Kids were crying,” he says. “They showed themselves what they could accomplish if they worked hard.” That’s what it’s all about for Woodrow Wilson’s new head coach and athletic coordinator. The Chicago native took over for Bobby Estes, who resigned in December after more than 20 years at the school. It may be Benedetto’s first head coaching job, but he has plenty of football experience. He played receiver for four years at the University of Sioux Falls before moving to Dallas and serving as offensive coordinator at Spruce for six years. Last year, he was the special teams coordinator at Mesquite Poteet, where he learned about mentorship opportunities for his players. He says, “When I left, I knew I could put those programs in place wherever I went.”
Taking over as Woodrow Wilson’s head coach and athletic coordinator is no small task, but Benedetto’s track record shows that he knows how to build a winning culture from the ground up. His players’ emotional response to making the playoffs at Spruce proves that hard work and commitment can transform a team — and those lessons extend beyond the field into every part of life.
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Why did you want to be a coach?
To be a head coach and an athletic coordinator, I have the biggest ability to impact the most kids. You can use high school athletics to teach responsibility, ownership and teamwork. You can put your stamp on a community for decades.
How did being an assistant prepare you for this job?
When you first start, you think, “I could be a head coach. I have so many ideas.” But then every year goes by, and you learn something new. You never know when you’re completely ready. Last year, (Mesquite Poteet coach) Kody Groves showed me how to delegate and how to lead strongly but not loudly. That prepared me to see the ins and outs of a successful program. It’s not just winning and losing. It’s how you impact the kids.
What do you love about Woodrow?
When you hear Woodrow Wilson, the name just means something. It’s a school with great tradition. It’s a microcosm of the country. It has affluent students. It has low-income students. We have a deaf population. They have the chance to make friends from all different cultures and learn to get along and work together. You can’t get that anywhere else.
How would you describe this Woodrow team?
Fundamentally sound players with discipline and energy. Kids who stick together through adversity. Our theme this year is brotherhood. I make the kids tell me something about somebody on the team. We put them through tough situations to see if they’ll crack.
“It’s not just winning and losing. It’s how you impact the kids.”
You come from a family of coaches. How has that influenced you?
My dad was a coach. I have an older brother who coaches in college and a younger brother who is a high school coach. We all played in high school and college. We ate, slept and breathed sports. Our wives get mad because when we go back, all we do is draw stuff up and talk about football. It unified our family. It helped us form our beliefs and work ethics.
What’s the hardest part about being a coach?
The hardest part is when you see a student-athlete that you invest so much in continually make the same mistake. We have a kid who skips class a lot. You sit down and talk to him, and he gets it. A week later, he’s skipping class again. The next hardest thing is someone who does everything right but doesn’t quite get a scholarship or a test score. That hurts your heart big time.
How do you handle the pressure of this job?
I’m not very good at that. The season is stressful. You want to win. The community wants you to win. Before I had kids, I’d come home and talk with my wife, but it would just sit with me. I’ve had a couple bad days here, but when I open the door, a 3-year-old and a 2-year-old are running to my legs to hug me. Whatever I was mad about, I’m like, “That’s stupid. It doesn’t matter.” The biggest way is to just enjoy my family, play with my kids and see their love for me whether we win or lose.

Photo by Danny Fulgencio.
What’s your favorite sports memory?
As a player, my dad was my coach. He was really hard on me and wouldn’t really tell me, “Good job.” One time I completed a pass to seal a game, and I looked over on the sideline, and my dad gave me a thumbs up. That’s something I’ll always remember.
What do readers not know about you?
I’m full Italian. My grandparents on both sides immigrated. At family parties, there’s a lot of pride. My grandma makes egg noodles and lasagna from scratch. She starts at 6 a.m. and will be done at 3 p.m. I have a unibrow that grows really fast. One year when I was teaching, I grew it out for my students because they passed a test. I didn’t play baseball in high school, but it’s my favorite sport. The Cubs are my favorite team. I used to know the starting lineup from when I was 7 to when I graduated high school.
This interview has been edited for clarity and brevity.