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, in 2026 the UPW Foundation awarded a total of $14,000 in scholarships:

• Five (5) $1,000 scholarships to local high school seniors
• Five (5) $1,000 scholarships to students currently attending college
• Two (2) $2,000 scholarships to students attending college and majoring in Political Science, Labor Studies, or Labor Relations

The scholarships are available to children/dependents of active United Public Workers members who are graduating high school seniors in the state of Hawaii or current college students who are continuing enrollment in the following Fall semester. Current college students do NOT have to be attending a university or college in Hawaii.

The UPW member must be in good standing at the time of the scholarship application and the child/dependent must be enrolled or enrolling in secondary education (college, university, trade, or vocational school).

A key component of the application process is a 1,000-word maximum essay.

In 2026, for applicants who were a high school senior or current college student and applying for the $1,000 award, their essay had to answer the prompt: “How does your experience growing up in a union household influence your future career goals?”

For applicants who were majoring in Political Science, Labor Studies, or Labor Relations and applying for the $2,000 award, their essay had to answer the prompt: “How does today’s social and political environment shape your understanding of unions and their role in the future?”

Along with the essay, all applicants were required to submit a headshot photo of themselves in JPG, PNG, or TIF format. This photo is used for scholarship-related promotional purposes and would only be used if the applicant was selected as a recipient of the Jimmy Toledo Scholarship.

Applicants were also required to submit their parent’s/guardian’s contact information and workplace information as a UPW member.

The deadline for the 2026 Jimmy Toledo Scholarship was Friday, April 17, 2026.

Applicants who were selected as a recipient of one of the scholarship awards were required to submit proof of enrollment/commitment at their college/university/higher education for the $1,000 award or proof of major for the $2,000 award prior to sending the award check.

Stay tuned for the announcement of the 2027 Jimmy Toledo Scholarship in early 2027.

Essay grading:

• 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 demonstrates UPW values (10 points)
• Maximum score is 30 points

Each essay is blind-graded by five (5) judges for a maximum total score of 150 points.

For the five (5) $1,000 awards to local high school seniors, each award is given to the applicant with the highest-scoring essay from eligible applicants within each UPW Division (Hawaii Division, Kauai Division, Maui Division, Oahu Division, Private Sector Division). In the event there are no applicants from a UPW Division, that Division’s scholarship will be awarded to the applicant with the second-highest overall essay score and so on.

For the five (5) $1,000 awards to current college students, the awards are given to the five applicants with the highest-scoring essays out of all eligible applicants.

For the two (2) $2,000 awards to current college students majoring in Political Science, Labor Studies, or Labor Relations, the awards are given to the two applicants with the highest-scoring essays out of all eligible applicants.