The James “Jimmy” Toledo Scholarship

The Next Generation of Leaders​

The United Public Workers Foundation launched the James “Jimmy” Toledo Scholarship in 2024 as a testament to the enduring legacy of a revered union leader and advocate for workers’ rights in Hawai’i. This scholarship aims to support the educational aspirations of United Public Workers member dependents, fostering the next generation of leaders and thinkers in the labor movement.

Stay tuned for details on how to apply for the 2025 James “Jimmy” Toledo Scholarship.

Everything You Need To Know

This is more than just financial assistance; it’s an opportunity to grow, learn, and carry forward the torch of leadership and commitment that Jimmy represented.

The United Public Workers Foundation is proud to present the James “Jimmy” Toledo Scholarship, a testament to the enduring legacy of a revered union leader and advocate for workers’ rights in Hawai’i. This scholarship, launched in 2024, aims to support the educational aspirations of UPW member dependents, fostering the next generation of leaders and thinkers in the labor movement.

To support educational advancement across our diverse membership, the UPW Foundation awarded five scholarships in 2024, each valued at $1,000. One winner was selected from each UPW Division to receive financial assistance designated for higher learning.

The scholarship is available to current graduating high school seniors in Hawaii who are children/dependents of an active United Public Workers member. The UPW member must be in good standing for at least one year and the child/dependent must be enrolled in secondary education (college, university, trade, or vocational school).

A key component of the application process is a 500 to 1,000 word essay. For scholarship applications in 2024, essays addressed the prompt: “How has growing up in a union household influenced your perspective on work and labor rights in Hawai’i?” This question invited applicants to reflect on their experiences within union households and the impact of such environments on their views regarding labor rights and work ethics.

Details on how to apply for the 2025 Jimmy Toledo Scholarship will be coming soon.

  • Central idea is clear and developed in answering the prompt question (10 points)
  • Usage of grammar and mechanics (i.e. spelling, punctuation) effectively communicates idea (10 points)
  • Essay demostrates UPW values (10 points)


Each essay is blind-graded by five judges for a maximum score of 150 points. In the event there are no submissions from a UPW Division, the scholarship will be awarded to the second-highest overall score and so on.

The United Public Workers Foundation is a private corporation designated as a 501(c)(3) organization by the Internal Revenue Service. It is a legally separate entity from United Public Workers, AFSCME, and AFL-CIO. However, the United Public Workers Foundation works closely with these organizations and others in the community exclusively to further the education of past and current United Public Workers members and members families by providing scholarships to help with educational programs, opportunities, and schooling as determined by the Board of Directors.

2024 Jimmy Toledo Scholarship Recipients

Isabella Clay, Kalaheo High School

Carma Tabilisima, Keeau High School

Maddox Tyau, Maui High School

Melina Espino, Kamehameha Schools Maui

Kiana Cueto, Damien Memorial School

About James “Jimmy” Toledo

The scholarship and golf tournament honor James Toledo, affectionately known as Jimmy, a figure synonymous with leadership and dedication within United Public Workers. Toledo’s contributions were manifold; as Chief Steward of the Board of Water Supply where he worked for over 30 years, a member of the State Executive Board, and the BU 01 Executive Negotiating Committee. 

He was instrumental in securing protective provisions for working families in the union’s contract legislation. His unwavering commitment to the well-being of UPW members and their families left an indelible mark on our union and its legacy. Toledo sadly passed away in 2013 at the age of 72.