Kapa‘a High’s Tommy Cox Named Top DOE Principal, Receives $25K from Island Insurance Foundation - Island Insurance | Island Insurance

Kapa‘a High’s Tommy Cox Named Top DOE Principal, Receives $25K from Island Insurance Foundation

Tommy Cox, principal of Kapa‘a High School on Kaua‘i, has won the 18th Masayuki Tokioka Excellence in School Leadership Award, announced earlier this evening at the Public Schools of Hawai‘i Foundation annual gala.

As the year’s top DOE principal, he receives $25,000: a $10,000 personal cash award and $15,000 toward a school project of his choice.

Principals Sheldon Oshio of Waikele Elementary and John Wataoka of Wai‘anae Intermediate were named semi-finalists from among the 15 outstanding principal nominated. Principals Oshio and Wataoka each received a $2,000 cash award for the honor tonight.

Island Insurance Foundation Chairman Tyler Tokioka announced the three top principals.

“With his Career Academies and Early College initiative, Principal Cox exemplifies the type of leadership and innovation that is transforming our public schools into model learning institutions for students of all abilities, no matter their post-graduation plans,” says Tyler Tokioka, grandson of Masayuki Tokioka. “By recognizing Principal Cox’s accomplishments and highlighting those creative programs, we hope to inspire others in public education across the state.”

Hawai‘i DOE Superintendent Keith Hayashi, other DOE leaders and a wide array of statewide business leaders and elected officials were among the approximately 625 guests at the Public Schools of Hawai‘i Foundation annual dinner at the Sheraton Waikiki Hotel.

Principal Tommy Cox
Raised by parents who were both longtime teachers, Principal Cox initially took a different path and worked for almost three years as an accountant before deciding that he was destined to be an educator. He actually began his educational career in the Kapa‘a district – the largest geographic district on the island of Kaua‘i – 20 years ago when he accepted a position as an uncertified math teacher at Kapa‘a Middle School. Inspired after just that one term with sixth-graders, he went back to school to earn both a teaching credential and Master of Education. After teaching at both Kapa‘a Middle and Kapa‘a Elementary, Principal Cox has now led Kapa‘aHigh for five years.

Principal Cox believes that all challenges can be surmounted as Kapa‘a High guides its students to success. He shared, “As a school leader, I can clearly see that education is constantly evolving, and it is my job to ensure that each student gains the skills and knowledge to be successful no matter what path they choose to take after high school.”

School Project Supported by Award Funds: Model Tiny Home for Future Teacher Housing
Last year, Kapa‘a High’s Building and Construction Academy students approached Principal Cox with the idea of building sustainable tiny homes for their teachers new to the island – and those students actually built a model 10-foot by 12-foot home with a shingled roof, windows and door; the finished structure was eventually transformed into a counselor’s office.

With that experience under their belts, the administration and students now want to build a tiny home from a 20-foot shipping container. Kapa‘a High has already acquired the container, and the students have found community partners who will assist with the project’s construction and sustainable-energy elements. With the Masayuki Tokioka Excellence in School Leadership Award monies, Principal Cox will now be able to fully fund the project and purchase photovoltaic panels, a sustainable restroom facility, water hook-ups and furnishings for the home. The award will also fund a trailer to tow the tiny home as Kapa‘a High will showcase it around the island to pitch the idea to possible business partners.

18th Masayuki Tokioka Excellence in School Leadership Award
The award honors the late Masayuki Tokioka, founder of Island Insurance Company, Ltd. and a proud graduate of Hawai‘i public schools. It is presented annually by the Island Insurance Foundation to a local public school principal who is visionary, community-minded and innovative – all qualities that Masayuki Tokioka exemplified as a business and nonprofit leader. The award was established in 2004 and is underwritten by the Island Insurance Foundation.

Each of the 15 nominees for this year’s Masayuki Tokioka Excellence in School Leadership Award – who lead public elementary and secondary schools in all four counties – previously received a $1,000 cash award from theIsland Insurance Foundation at an event at the Island Insurance Center in Downtown Honolulu. The other outstanding nominees for 2024 were:

  • Lynne Ajifu, Mililani ‘Ike Elementary School
  • Allyson Doherty, Kailua Elementary School
  • Eliza Loha Kanahele Kaka, Lā‘ie Elementary School
  • Gary Kanamori, Nāhiʻenaʻena Elementary School (Lahaina)
  • James Kau, ‘Aiea Intermediate School
  • Marc Kawahara, Kalihi Kai Elementary School
  • Hannah Loyola, Kohala Elementary School
  • Ty Ogasawara, Pukalani Elementary School
  • Joseph Passantino, Keʻelikōlani Middle School (Downtown Honolulu)
  • Tiffany Pratt, Kaʻūmana Elementary School (Hilo)
  • Wilma Roddy, Nāʻālehu Elementary School
  • Kim Sanders, Ewa Makai Middle School

Masayuki Tokioka
After graduating from McKinley High School, the late Masayuki Tokioka – a fervent believer in the power of education – earned a Bachelor of Arts from the University of Hawai‘i at Mānoa and a Master of Business Administration from Harvard University. Over a business career that spanned seven decades, he founded a number of highly successful local enterprises including Island Insurance Companies, International Savings & Loan Association and National Mortgage & Finance Company. He was also dedicated to the community, serving as the driving force behind the Japanese Cultural Center of Hawai‘i, the Crown Prince Akihito Scholarship Foundation and the Hawai‘i Immigrant Preservation Center.

About Island Insurance Foundation
The Island Insurance Foundation is the charitable arm of Island Insurance, Hawai‘i’s only locally owned and managed property and casualty insurance carrier.

Since 2003, the Foundation has donated over $13 million to a wide array of non-profit organizations across Hawai‘i. It donated almost $1.4 million to over 100 local non-profits in 2023 and is recognized as one of the top 25 most active private foundations in Hawai‘i.

Founded in downtown Honolulu, Island Insurance has been serving Hawai‘i’s families and businesses for over 80 years. Island Insurance is the only Hawai‘i-based company to be recognized as a Top 50 property & casualty insurer in the nation by the Ward Group for an unprecedented 16 consecutive years. It holds a financial strength rating of “A” (Excellent) from A.M. Best Company.