Two longtime Neighbor Island leaders of the Hawai‘i State Department of Education will retire at the end of the school year, concluding a combined 77 years of service to public education. Kaua‘i Complex Area Superintendent Daniel Hamada and East Hawai‘i Complex Area Superintendent Esther Kanehailua have led distinguished careers defined by steady leadership and a deep commitment to community.

“Mahalo to Danny and Esther for their decades of leadership and dedication,” Superintendent Keith Hayashi said. “They’ve led with heart, purpose and deep pride in their schools and communities. Their legacy will continue to shape generations of students and educators, and we are grateful for their incredible service.”

Daniel Hamada: A pillar of Kaua‘i education

Hamada’s career with the Department spans an impressive 47 years. From his early days as a teacher to his role as principal at Kapa‘a High for eight years, and later as Kaua‘i Complex Area Superintendent for seven years, he’s helped shape the island’s educational landscape. He also served four years as HIDOE’s Assistant Superintendent for Curriculum, Instruction and Student Support.

After retiring in 2018, Hamada returned to lead once again in 2022, stepping in as interim complex area superintendent. That same year, he was honored as the first University of Hawai‘i College of Education Alumni Association Kaua‘i Distinguished Alumnus.

Reflecting on nearly half a century working with students, Hamada said it’s the strength of the Kauaʻi community and their respect for the public schools that gives him faith in the island’s youth. He hopes students recognize this and “choose to come back (home) and give back to support the community” that has given them so much.  

As a mentor to many Kauaʻi teachers and administrators, including his successor, Leila Maeda-Kobayashi, Hamada has this advice to rising educators: “Build trust and relationships with your students. Learn what type of learner they are and walk the talk. Students are always watching.”

Maeda-Kobayashi, currently deputy complex area superintendent for Kauai‘i, will step into the lead role on July 1. A Kaua’i High graduate, she began her education career in special education at Waipahu Elementary before returning home to Kaua‘i as a special education teacher at Kōloa Elementary.

She comes from a distinguished educator lineage; her mother, Amy Maeda, held positions as the district superintendent of Kauaʻi and Leeward Oʻahu districts. 

In her 28 years with the HIDOE, Maeda-Kobayashi served as a principal at Koloa Elementary for seven years and was named a semi-finalist for the Masayuki Tokioka Excellence in School Leadership Award in 2023. Prior to that, she was the vice principal at Wilcox Elementary for three years. 

Her vision for the complex area: Success for All. She aims to instill in her students the knowledge and confidence that when you come out of a Kauaʻi public school, whatever path you choose – college, career or trade school – you can make it anywhere. 

Esther Kanehailua: Leading with heart in Hilo

Kanehailua retires with 30 years of service to Hawai‘i public schools. A proud Hilo High alum, she returned to her roots as a teacher, then rose through the ranks as a vice principal, principal and eventually, complex area superintendent overseeing 13 schools in East Hawai‘i.

Kanehailua started her education career as a teacher at her alma mater and later served as vice principal for Hilo High, Hilo Intermediate and Waiākea High and principal at Haʻaheo Elementary and Hilo Intermediate. She became the Hilo-Waiākea Complex Area Superintendent in 2019, and also served four years as a commissioner on the Accrediting Commission for Schools, Western Association of Schools and Colleges, representing HIDOE. 

Looking back, Kanehailua says it’s the people who left the biggest impression.

“I’ve been super blessed to work with a lot of good educators – that is my biggest takeaway. There’s just so many good people that I’ve worked with over the years – teachers, counselors, custodial staff, cafeteria staff, vice principals, principals, educational assistants, you name it. I’ve gotten to work with so many people who are committed to public education. So many of our kids are in our schools and we want the best for the community and it’s their commitment to the community and what public education can provide.”

Succeeding Kanehailua is Kasie Kaleohano, currently deputy complex area superintendent and a former student of Kanehailua’s at Hilo High. Raised in Keaukaha, Kaleohano brings a strong connection to the community she now serves.

“She’s a great problem solver, she gets in there and wants to help,” Kanehailua said of her successor.

Kaleohano was raised in the small homestead community of Keaukaha on Hawai‘i Island and is a respected kumu hula. She earned her bachelor’s degree in education from the University of Hawai‘i at Mānoa and a master’s degree in teaching from National University. After 11 years as a teacher at Waiākea High School, she transitioned to school administration spending time as vice principal of Prince Jonah Kūhiō Kalaniana‘ole Elementary & Intermediate School and later served as principal of Waiākeawaena Elementary. She then became a district educational specialist for the Hilo-Waiākea Complex Area before stepping into the deputy CAS role in January.

As for what’s next, Hamada is looking forward to traveling and hitting the tennis courts. Kanehailua is eager to spend more time with her family and dog — and maybe learn how to bake focaccia bread.

Both Maeda-Kobayashi and Kaleohano will start their new roles on July 1.