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Supporting Tomorrow’s School Leaders

November 26, 2025

Kathy Jaycox dedicated her career to advancing education as a high school teacher, university professor and community college administrator. Now in retirement, she’s proud to continue that support, including with a new scholarship that honors her uncle—a longtime educator himself.

The Andrew J. Penn Endowed Scholarship at Chaminade’s School of Education and Behavioral Sciences targets aid to students pursuing a master’s degree in education. While many scholarships are for undergraduates, Jaycox said it was important for her to help graduate students who are returning to school and looking to build on their skills and advance as leaders in education.

Jaycox says her “Uncle Andy,” who passed away in 2010, inspired her to pursue a career in education and often spoke about how he taught school during the day and earned his master’s degree at night. Penn served as a principal in Chicago for more than two decades.


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Penn, who started teaching in the 1950s, was also a Korean War veteran and something of a big brother to Jaycox. “He was a really big part of my life for as long as I can remember,” she explained.

“He put other people ahead of himself so much.”

Jaycox and Penn not only shared a passion for education. They also both fell in love with Hawaii, visiting for vacation and vowing to move there someday.

That’s exactly what they did in the early 1990s during a particularly chilly Chicago winter. Penn was retired by that time and Jaycox was able to secure a position at Honolulu Community College focused on continuing education.

Jaycox served at the University of Hawaiʻi for nearly 20 years and also led the Hawaiʻi P-20 Initiative to strengthen the education pipeline from early childhood to postsecondary education.

She said during her years in education leadership, she learned about Chaminade and its service-focused mission. Penn also supported the University as a donor. Jaycox said the endowed scholarship not only celebrates her uncle’s legacy, but her own pursuit of lifelong learning.

“I know this scholarship is what Uncle Andy would have wanted,” said Jaycox, who returned to Chicago after her retirement.

“He would often talk about how important it was to help people who wanted to do something more. As a lifelong learner myself, it’s nice to help somebody do that.”

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Posted by: University Communications & Marketing Filed Under: Campus and Community, Education, Featured Story, Homepage Tagged With: Master of Education

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