Jenna Stewart smiles and hugs kids in her class

Jenna Stewart, a 5th-grade mathematics teacher at Longbranch Elementary School (Boone County), celebrates with her students after she was named a Milken Family Foundation National Educator Award winner. Photo by Joe Ragusa, Kentucky Department of Education, Dec. 11, 2024

(UNION, KY) – Jenna Stewart, a 5th-grade mathematics teacher at Longbranch Elementary School (Boone County), was celebrated on Dec. 11 as the latest Kentucky educator to receive the Milken Family Foundation National Educator Award.

Stewart was presented with the award, which includes a $25,000 unrestricted cash prize, in a surprise ceremony at her school that included students, faculty, and district and community leaders.

The prestigious award, hailed as the “Oscars of Teaching,” was presented by Kentucky Commissioner of Education Robbie Fletcher, First Lady of Kentucky Britainy Beshear and Milken Educator Awards Senior Vice President Jane Foley. This school year, up to 45 recipients across the country will be honored and celebrated as part of the Milken Family Foundation’s journey to the 3,000th Milken Educator, which was named earlier this year.

“It is teachers like Ms. Stewart who are helping us move forward with our United We Learn vision to provide vibrant learning experiences for our students,” Fletcher said. “She is a role model as she focuses on the whole child, ensuring that every student receives the care and attention they need to thrive–not only in their learning but socially and emotionally.”

Stewart said she was shocked when she heard her name called in an assembly that included all of her school colleagues and the entire student body.

“I couldn’t be the teacher I am today without the support from the other teachers and staff members,” she said. “And my students are what make me want to continue being a teacher.”

Stewart graduated from the University of Kentucky in 2014 with a bachelor’s degree in elementary education and is currently working on a master’s degree in school counseling from the University of the Cumberlands.

Longbranch Elementary is one of 15 elementary schools in the Boone County school district. The school prides itself on its Leader in Me initiative, which is a whole-school improvement process based on the idea that everyone can be a leader.

Beshear said she was excited to join in celebrating Stewart. She described some of the qualities that make her a special teacher.

“Ms. Stewart’s dedication to the field of teaching is evident in her daily actions,” she said. “She consistently goes above and beyond to create innovative methods of student learning, ensuring that her classroom is a place where every student, regardless of their abilities, feels not just included, but genuinely valued.”

Jenna Stewart holds a check signifying her $25,000 Milken Educator Award prize while posing with Jane Foley, Robbie Fletcher, Stephanie Stambaugh, Britainy Beshear, Jeff Hauswald and Glyptusann Grider Jones

Jenna Stewart holds a check signifying her $25,000 Milken Educator Award prize while posing with Milken Educator Awards Senior Vice President Jane Foley, Kentucky Commissioner of Education Robbie Fletcher, Longbranch Elementary School Principal Stephanie Stambaugh, First Lady of Kentucky Britainy Beshear, Boone County Superintendent Jeff Hauswald and KDE Director of Education Policy Glyptusann Grider Jones. Photo by Joe Ragusa, Kentucky Department of Education, Dec. 11, 2024

From her colleagues, Stewart is known for connecting with her students on a personal level by understanding their unique needs and strengths. This rapport extends beyond the classroom, as she fosters a strong sense of community and trust among parents and colleagues. Relationship-building is known as the cornerstone of Stewart’s success and makes her a strong teacher.

Through her positive reinforcement and encouragement, Stewart celebrates her student’s achievements both in and out of the classroom, building her students’ self-esteem and motivation by making them feel valued and supported in their educational journey.

“Jenna Stewart shapes the minds and futures of her students, inspiring them to reach their full potential,” said Foley, who herself is a 1994 Indiana Milken Educator. “Her unwavering leadership, supportive learning environment, and strong community relationships make her a role model for students and colleagues alike. Congratulations, Jenna, and welcome to our national Milken Educator Network!”

Created by Lowell Milken in 1987, the Milken Educator Awards publicly recognize excellence in teaching not only to inspire educators but also students and communities to “Celebrate, Elevate and Activate” the American K-12 teaching profession. 

Milken recipients do not apply to receive the award. Candidates are selected through a confidential process and are then reviewed by blue ribbon panels appointed by state departments of education.

This season, the Milken Educator Awards will reach more than $75 million in individual cash prizes since the awards’ inception in 1987 and more than $145 million invested in the Milken Educator Award national network overall, empowering recipients and encouraging young, capable people to consider a career in education.

The Milken Educator Award is not a lifetime achievement honor. Recipients are sought out while early to mid-career for what they have achieved – and for the promise of what they will accomplish given the resources and opportunities afforded by the award.

In 2025, Stewart and the other award recipients from across the country will attend the Milken Educator Forum, where they will network with their new colleagues and exchange ideas with state and federal leaders on the future of education.

In addition, they enter the Milken Friends Forever mentoring program, where freshman Milken Educators receive personalized coaching and support from a Milken Educator veteran on ways to elevate their instructional practice and take an active role in educational leadership, policy and practice.

For more information about Stewart and links to photos and a video from the ceremony, visit the Milken Educator Awards website