The 2025 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.

Learn more about the 2025 Jimmy Toledo Scholarship below and apply today.

The deadline to apply is Thursday, May 1, 2025.

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.

For 2025, the UPW Foundation is expanding its awards and offering nine scholarships with a total value of $10,000:

  •  Five (5) $1,000 scholarships for local high school seniors
  • Three (3) $1,000 scholarships for current college students
  • One (1) $2,000 scholarship for a college student majoring in Political Science, Labor Studies, or Labor Relations

The scholarships are available to high school seniors graduating in 2025 in the state of Hawaii and current college students who are children/dependents of an active United Public Workers member.

Current college students do NOT have to be attending a university or college in Hawaii.

The UPW member must be in good standing for at least one year at the time of submission and the child/dependent must be enrolling or 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 applicants who are a high school senior or current college student and applying for the $1,000 award, your essay must answer the prompt: “How has UPW helped or benefited your family while you were growing up?”

For applicants majoring in Political Science, Labor Studies, or Labor Relations and applying for the $2,000 award, your essay must answer the prompt: “Why is being a member of a union still important today?”

Along with the essay, all applicants must submit a headshot photo of themselves in JPG, PNG, or TIF format. This photo will be used for scholarship-related promotional purposes and will only be used if you are selected as a recipient of the Jimmy Toledo Scholarship.

The deadline to receive your application is 11:59pm HST on Thursday, May 1, 2025.

If you are selected as a recipient of one of the scholarship awards, we will require proof of enrollment/commitment at college/university/higher education for the $1,000 award or proof of major for the $2,000 award prior to sending the award check.

  • 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 will be blind-graded by five (5) judges for a maximum score of 150 points.

For the five (5) $1,000 awards to local high school seniors, each award will be given to the highest-scoring essay from an applicant from each UPW Division (Hawaii Division, Kauai Division, Maui Division, Oahu Division, Private Sector Division). 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.

For the three (3) $1,000 awards to current college students, the awards will be given to the three highest-scoring essays out of all eligible applicants.

For the one (1) $2,000 award to a student majoring in Political Science, Labor Studies, or Labor Relations, the award will be given to the highest-scoring essay out of all eligible applicants. 

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.