The question wasn’t whether or not she would be an athlete, but rather, what sport she would play when she grew up. “The joke among my family was ‘I wonder what Nawai is going to do?’” she recalls.
As a child, her father exposed her to all types of sports - volleyball, track and field, and boxing, before landing on softball’s closely-related cousin, baseball. On the baseball field, Kaupe again found herself surrounded by other males and was the only female on the team. “Playing with boys encouraged me to give out more than my 100 percent,” she said.
She eventually became comfortable with this and it prodded her to separate herself as a competitor. It wasn’t until later on in high school that Kaupe would switch to softball — a transition that would prove to be rather uncomfortable at first. “When I joined the softball team and was surrounded by other girls and all that drama, I always secluded myself because I didn’t know how to handle it,” she recalled.
And it did make it any easier that her father Bernard was also involved in a stressful situation. He, along with the rest of the softball coaching staff at Baldwin High School was let go. WIth her father’s departure, Kaupe felt the pressure to transfer schools, going from Baldwin to Maui High, where her father would also join her as a softball coach for the Sabers. While the rest of her family had graduated from Baldwin High, she would eventually become the first to graduate from Maui High.