UK grad surprised with prestigious Milken Educator award, $25,000 prize

LEXINGTON, Ky. (March 3, 2025) — A University of Kentucky alumna received the surprise of a lifetime last semester.   

Jenna Stewart, a fifth-grade teacher at Longbranch Elementary in Boone County, Kentucky, thought she was taking her class to a school assembly as part of a visit from the Kentucky Commissioner of Education. The event, however, was designed to surprise Stewart with the Milken Educator award – an honor, considered the “Oscar of teaching,’ that comes with a $25,000 cash prize.  

Stewart says she was in a state of shock and confusion after hearing her name called. When media began attaching microphones to her clothing and she was asked to speak, a whirlwind of emotions hit. 

“It was a moment and day that I will remember forever,” she said. 

Stewart’s journey to becoming a teacher began at the UK College of Education. She credits the significant amount of time UK’s elementary education majors spend in area schools as helpful preparation for becoming a teacher. 

“It opened my eyes to the diverse populations and unique needs of different schools,” Stewart said. “Throughout my experience, I gained invaluable insights from each mentor teacher I worked with. My student teaching placement was where I developed the greatest confidence in my abilities as a future educator." 

UK College of Education Dean Danelle Stevens-Watkins, Ph.D., praised Stewart’s commitment to her students, saying, “Her career and passion are great examples of what we strive to develop among aspiring educators in our college.” 

Prior to her career in Boone County, Stewart spent two years teaching at Julius Marks Elementary in Lexington before moving back to her hometown. As a teacher, Stewart focuses on building relationships with her students.   

“Having the opportunity to positively impact the lives of students and push them to reach their highest potential is what I am passionate about,” she said. “Creating positive interactions and connecting with students to help push them to be the best that they can also helps drive my teaching.” 

She encourages those considering a teaching career to not only have a passion for working with kids, but to be open minded, flexible and willing to try new things. 

"Teaching is a transformative journey, and the enthusiasm and dedication you bring into the classroom can significantly impact the lives of your students,” she said.   

In receiving the Milken Educator award, Stewart was praised for the high academic and behavioral standards she sets for her fifth-grade class. A quiet leader, she places emphasis on relationship-building and works to instill a strong sense of community amongst students and their families, providing a sturdy foundation for structure and success.  

Stewart has coached "Girls on the Run," building confidence in students through setting and achieving their goals and completing a 5K. She has co-chaired the Student Job Committee, a group that helps students obtain jobs. She also has led the school's Lighthouse Team – a group of students who represent the school in a myriad of ways, from morning announcements to helping others board the buses – that is part of the "Leader in Me" program. Her sense of community is evident: she holds "porch pop-ins" at students' houses at the beginning of the school year to meet and encourage them for the year ahead and frequently attends her students’ sporting events outside of school.  

"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," said Kentucky Education Commissioner Robbie Fletcher, Ed.D., who presented the award with Milken Educator Awards Senior Vice President Jane Foley, Ph.D. "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."  

The Milken Educator award is an affirmation of the dedication Stewart pours into her students. 

“It has given me a boost of confidence and a burst of energy to keep doing what I do each day,” she said. “I am excited to connect with and learn from various people within the Milken community, continuing my growth as an educator and leader."