For Kalaheo native Jason Caldeira, life is good.
As a youth, he spent countless hours at the neighborhood center nearby his childhood home. He now looks after it as the facility manager.
He’s coached local youth football for several years. Today, he’s in his fourth season as the head coach of the varsity football program at his alma mater — Waimea High School.
Caldeira said he always wanted to be a family man. He’s happily married and has three young children. He even said taking on fatherhood has helped him become a better coach.
Caldeira sat down with The Garden Island and talked about working on the same grounds he spent his childhood on, and how becoming a parent made his change his approach to coaching.
What do you do here at the neighborhood center?
I’m the facility manager.
I organize and manage the facility. I’m, pretty much, in charge of all the activities that go on here. I start programs for kids and the elderly, the kupuna. I just do the daily services from here.
So, what do you have here at this center?
All centers are different, yeah? For our center, it’s really big with the youth programs. Every year, we do a County of Kauai winter basketball league that starts up around January and finishes right before April. That goes from the ages from fourth- grade up to the eighth-grade. We have over 300 kids, boys and girls.
After that season, it’s not a county-sponsored program, but it’s one of these groups that we represent — Ho’o Hui. They hold a termite basketball league. They go from kindergarten up to second- grade. That can be well over 500 kids.
We got other basketball leagues from random, different entities. We have a 35-and-over men’s league here, basketball. We have workout, like aerobics and workout programs. We have Zumba twice a week here. We have kupuna wellness, which is for the senior citizens, twice a week. We have tai chi once a week. We have a Hit Booty Camp, which is fast-paced, like cross-training. That’s more for the 18-and-over. That’s twice a week. We have kaju kenbo class over here.
We have a lot. We have taiko drums. We have a Japanese music class. We have our senior ukulele class. We have badminton during the daytime. And the biggest one lately, the biggest craze, is pickleball. We have pickleball twice a week, and that brings in more than 200 people.
Is it overwhelming? Dealing with 300 or 500 kids?
You say 300-500 kids, but it’s not like 300-500 kids at one time. The games will go from 8 a.m. up to 3 p.m., and then you have all the people go through it. I mean, it can be overwhelming but it’s usually fun. And then our job is recreation. We also participate in the county track meets.
We just got done doing a senior fun day at Lydgate. We do a senior Valentine’s Day dance, and senior arts and crafts. … We have Summer Fun here, where it’s 100 kids running wild over here and going nuts every day. We have Spring Fun. We have Winter Fun.
How long have you been working here?
I’ve been here about four years now.
You mentioned you spent a lot of time here as a kid. So, you have a lot of history here.
Very much, yeah. Mr. Tommy Nakamura was the manager here. I used to live right over there (nearby the center) in those two-bedroom apartments. It was, sort of, like low-income housing kind of deal. I’d play here in the morning, or even throughout the day. Whenever there was availability, Mr. Nakamura would let me shoot baskets, you know? And I would watch the older guys play. By the time I was 13, I was just as tall or taller. So I’d be playing open league games with them, or open gym games.
I used to come to the Summer Fun over here. It used to be a baseball park before it was a center. They used to have a lot of baseball games out here. These hills (pointing toward fencing around the parking lot), they never had this fence lined. It was kind of like hills. Everything was higher. We used to make bike ramps and jump up the bike ramps.
We used to do a lot of things.
Is it surreal that you spent so much time here as a kid, and now you work here?
It’s a trip. I’ll tell you right now, yeah. That’s why I feel like I’m lucky, you know? I grew up right there. I used to play here. It’s, like, sentimental a little bit. Or, I’ll say a lot.
Other than football, or unless you’re one of those guys who’s about football 24/7 all year long, what other interests do you have?
Growing up, I was a basketball guy. I love basketball. I love watching basketball. I used to love playing basketball. I play in these 35-and-over leagues.
I have a wife and three kids. In my off time, it’s spent usually just being dad — doing the normal day-to-day things. And whatever free time we have, we try to find something to do. Go to the beach, go fishing or just catch up at home. Clean the yard, you know? Just try to do the normal things, and try to catch up on the things we miss when we’re out there on the field.
Does it get tough balancing everything? Family, work and then football?
Yeah, it can get tough. But I got good support from my wife, Darrellyne. … She’s the coach’s wife. She knows how to support me in the right way, and I support her. It’s a team thing, you know? She puts out a lot, and I have to catch up and put out a lot, too. So whenever I do have free time, it’s to her and the kids. Just to have balance at home, you know?
How old are your kids?
Seventeen, 14 and 9. … And they’re my step-children. I was raising them for the last seven years.
What was it like stepping into that father role? From zero kids to three?
Oh, yeah. It’s a change of culture, you know? Change of lifestyles. But I couldn’t ask for a better group of kids. Couldn’t ask for a better wife. It’s funny how things worked out. It doesn’t sound like the most (ideal situation) — you’re stepping into a role and all of a sudden you’re a father, you know? Doesn’t sound like the most exciting thing, but it really has been. It was the best thing that ever happened to me.
I really believe without meeting my wife, I wouldn’t be where I’m at today. I’d still be a little lost, trying to find out what’s my purpose here on this earth. With my wife, I know why I’m here now. She made me a father and a husband, and I think that’s helped me be a better coach. I was a coach before I met her, but now I feel like I understand thing a whole lot better. She completes me.
How did you meet her?
We actually knew each other from when we were kids. We grew up in the same town, and we went to the same school. She’s a grade above me. … She grad in ‘97 and I grad in ‘98, but we’re basically the same age the majority of the year. So techically, I’m with an older woman.
Her first cousin was my best friend growing up. … So, I knew her since I was little but we weren’t that close. We became friends when we were 15. We both went to Holy Cross Church, and we both went to the same confirmation class. That’s when I got to know her better. That’s why years later when we hooked up, or re-met I guess, I kind of knew already on my first date what kind of girl she was.
I always thought she was a good girl, pretty, you know? That kind of helped me pursue that, pursue her. I was looking for somebody different. Darrellyne’s different. She’s mellow. She’s not out partying. I know she’s a responsible girl with a good head on her shoulders.
So there wasn’t any mystery? You already knew everything about her?
Oh, yeah. Like I knew her, yeah. That’s why after our first date, I was like I kind of knew already. Like, “I’m going to marry this girl.”
I knew pretty fast. Like, after a week. And if you ask her, she’ll tell you the same. It was just like that.
You said parenting helped you become a better coach. In what ways?
I was a coach before I became a parent, but they kind of helped each other at the same time.
Before I was a parent, I approached the kids as an older brother kind of deal. My sympathy for them or the way I would give them advice, it came off as an older brother because I looked at them like my younger brothers, you know?
When I became a father, and as I’m starting to get older, all of a sudden I started viewing these kids like my sons. Then I have these different worries about them all of a sudden. It just seems like I’m thinking about it more, like, “I hope they grow up for this, man.” Or, “This guy, he really got to change this. He’s going to have a hard time when he gets older.” My worries and my sympathies were completely different. It was like a father.
When you’re an older brother, it’s like, “Brah. If you don’t do this, it’s going to be like this.” And then it’s like, “Well, I told you.” Now when you’re a father, you tend to be like, “Don’t do it.” I don’t know. I guess I worry more about the little things. … Like, I really want them to turn out to be functionally in this society, you know? Like I do for my kids, I just want them to be (good). I don’t want to see them fail in anything.
What was it like changing the way you approached coaching?
You just got to adapt, just like anything. I’m lucky, you know? I had good parents and stuff. I just kind of knew it was my time to be like them. I have to be that way — that solid foundation at home, or now for football, that solid guy that’s going to be there every day. I got to make sure I got the answers for them. Like how I got to make sure for my wife, there’s needs to be addressed, and I got to make sure I got the answers for her and for my kids. I just got to be able to provide that. Whatever it is, I just got to make sure I can help provide what it is for them.