Leo Caires, a 1996 graduate of Maui High School, played professionally with the El Hospitale Pioneers in Barcelona for a season after a standout career at the University of Wyoming. — Photo courtesy of Leo Caires
Leo Caires doesn’t have time for much sleep.
The former Maui High School, University of Wyoming and pro linebacker has grown into a family man, farmer, entrepreneur, business man and community leader on the Valley Isle.
“I think about all the folks who contributed to where I’m at today, just kind of reflection,” the 42-year-old Caires said this week. “Family, the journeys that they’ve made to put me where I’m at, so everything I do is to honor all those people, my family, who have helped me to get where I’m at.
“Crazy journey, crazy story, for sure. It’s been a hell of a time, it’s just unreal.”
In 2015 Caires was selected for the First Nature Futures Program through Stanford University and Kamehameha Schools — it went a long way to shaping his mindset today.
Leo Caires (back center) is pictured with his ohana on their 25 acres of land in Kula, where they have started the Kaupakalua Wine and Liquor Company. — Photo courtesy of Leo Caires
“The objective of the program was to bring young, indigenous leaders from their communities together from Alaska, the Alaska natives, the Maori from New Zealand and Hawaiians,” Caires said.
At the program he met a gentleman from New Zealand “and we were having dinner one night and I described how sometimes you want to see so much results in your lifetime and you’re so driven and so determined to see results now. He quickly put it all in perspective to me.
“He said, ‘That’s exactly how we do it, but in a longer term, Leo. I know that all this effort and transformation that I’m trying to do now is not going to happen for the next three generations, but that’s how I look at my life. You do things for folks that are not even here today.’ “
Caires focused on building leadership among Native Hawaiians “and when I came out of that, I focused on my life and now the things that I do today are really for my great grandchildren. Unborn people, and that’s how I look at my life now. … The generations before me, I pay a lot of honor and respect to them as well.”
Patricia Keonaona Atay Caires and Joseph Caires Jr. clearly raised a special son. Leo Caires also helps take care of a fish pond in Hana from his mother’s side of the family, an 11-acre pond called Hokuula.
A bottle of Kaupakalua Wine andLiquor Company’s lilikoi wine is shown. — Photo courtesy of Leo Caires
“That really instilled a lot of respect for culture, respect for land,” Leo Caires said. “And children and kupuna and having another long-term view on the world as well.”
He has four children with his wife, family court judge Adrianne Nalani Heely-Caires.
“Being a father is like football camp every day, you’re tired, get little sleeping, you’re sore, but you just keep getting up every day excited to play another day,” he said. “The only difference as a father is that you love it more than anything else.”
Caires originally went to Wyoming for rodeo, but soon after arriving there, he walked on to the football team. Soon after that, he earned a scholarship and was a two-season team captain.
“My college roommate at the time said, ‘Hey man, you’re from Hawaii and you ride bulls and steer wrestle, why don’t you come out and try come out to the football team?’ “ Caires said. “Then, I did.”
A severe broken right leg at Wyoming didn’t stop Caires from leading the Cowboys in tackles as a senior and landing a spot in the Hula Bowl, held on Maui.
On Feb. 2, 2002 — the date rolls off his tongue — he broke his left leg worse than the right leg late in the college All-Star showcase at War Memorial Stadium despite being named Defensive Player of the Game.
The left-leg injury, which included a fibula fracture and dislocated ankle, and the six months of rehabilitation that followed knocked Caires off the NFL draft boards of every team.
“I had to get plates and pins, which I still have today,” he said. “The ankle just took me a very long time to rehab, to get the flexibility and get the stiffness out.”
Once reasonably healthy, he did get a hard look in the Canadian Football League’s tryout camp and later played a season in Barcelona for the El Hospitale Pioneers.
“It wasn’t as competitive as the NFL by any means, but what I really got out of it was an all-expense-paid opportunity to really go see the world,” Caires said. “It was really culturally enriching and really gave me kind of a global perspective.”
That perspective led to the path he has traveled for the past 16 years.
“Every college Division I-A football player goes through it, you’re pursuing this dream, and for me, it ended short after my injury,” Caires said. “However, I was still given a few opportunities to pursue football, but because of my position as a linebacker after my tenure in Barcelona, I just felt that my body was ready to rest. I was at peace.
“I knew there was another kind of game to pursue for me.”
Retired Maui High football coach Curtis Lee remembers starting Caires as a quarterback when he was a sophomore before discovering that he was a rodeo cowboy.
“I found out that he was doing bull riding and I said, ‘We cannot have this, I don’t need my quarterback riding bulls,’ “ Lee said. “So, I said I think maybe we’ll try this kid as a linebacker if he does that for pleasure — we did and like they say, the rest is history.”
The undefeated 1995 Neighbor Island Football Championship team when Caires was a senior, along with eventual Hawaii standout Robert Kemfort, was special.
“The greatest team I ever coached,” Lee said.
Lee looked at Caires as nearly a son of his own.
“Amazing, he’s one of those special kids, just really talented, committed,” Lee said. “He’s one of those guys that once he makes up his mind he’s going to do something. And he’s going to give it all he’s got. He’s loyal. I don’t know what words I can say that haven’t been said.”
After Barcelona, Caires moved to Honolulu where he worked in finance for about a year and a half before coming back to Maui. He then went into the solar energy business, starting Genex Energy.
“We spent the next six, seven years, all the way up to 2013 working on projects like the Maui County Solar Project — we did the project that today saves the taxpayers money on county sites through solar energy,” Caires said. “This project was a huge, aggregated project where we had to install and to develop solar at no cost to the county, at all kinds of different places.”
Those locations included the Kihei Aquatic Center, several fire stations, the waste water treatment plant and Kaunoa Senior Living Center, Caires said.
“It was just a massive undertaking and we had to do it in just a very short time and we were able to pull it all off,” Caires said.
He graduated from Wyoming with an animal science degree. While running Genex, he earned his masters of business administration over two years studying online with Chadron State College in Nebraska in 2014. He later got a doctorate of education degree in leadership and innovation, also online, from St. Thomas University in Miami in 2018.
He did his doctorate dissertation on the financial literacy of Native Hawaiians.
“I also looked at how to help my family with their agricultural lands,” Caires said. “We were looking at different initiatives and then I asked my dad, ‘I remember you always making wine, making homemade wine.’
“My dad used to always talk about this old winery in Kaupakalua, so now here I am, very interested in this and we discovered that the original winery got started in 1905. So as a family business today, we actually relicensed the winery. It was called Kaupakalua Winery and Liquor Company. So with my dad’s permission and blessing I went ahead and we went ahead and pursued all the licensing. … It took us about five years.”
While working on the permits for the winery, Caires was hired by the U.S. Department of Commerce in 2018.
“My job, my tour of duty was Census Bureau and local organization of local government to help promote and educate the public and provide support for the large census that happens every 10 years,” he said. “It was challenging and a very rewarding experience.”
On that job he went to Kalaupapa to help the count.
“Just that experience, an overwhelming experience of emotion,” Caires said. “When I returned I shared my whole experience with my children. It just kind of changed my view on being a father.”
After finishing his two-year run with the Census, he currently works for the U.S. Small Business Administration.
Now with his father’s help, the winery makes fruit brandy and fruit wines. Caires bought 25 acres in Kula a few years ago for the fruits that go into the winery. The family still has cattle on the family’s Kaupakalua land, which also takes a lot of Leo’s time.
The first wine and brandy are ready for sale after two years of fermentation. They are made with lilikoi, guava, strawberry guava, panini and black cherry.
“We just finished the first aging of our wines and our spirits and I’m just sending the first shipment to Japan as we speak,” Caires said. “The fruits of our labor. … We’re still just a family-style, boutique winery.”
* Robert Collias is at rcollias@mauinews.com
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