UNION, Ky. — It’s called the “Oscars of Teaching,” and a Boone County teacher at Longbranch Elementary, has received the national Milken Educator Award, an award founded by the Milken Family Foundation. 

What You Need To Know

  • The Milken Educator Award honors teachers who demonstrate exceptional teaching skills and inspire their students.

  • Jenna Stewart is the sole recipient in Kentucky this year

  • Stewart was awarded a $25,000 prize and national recongition

  • This year, 45 educators nationwide will be awarded

Jenna Stewart, a fifth-grade math and social students teacher in Union, was named the 2024-25 Milken Educator recipient in Kentucky. 

The announcement came during a school assembly where students, staff and community members gathered for what they thought was a celebration welcoming Kentucky Commissioner of Education Dr. Robbie Fletcher. When Stewart’s name was called, cheers erupted amongst the crowd and Stewart seemed to be at a loss for words. 

She said, “I just won a $25,000 educator award,” as she proudly told her dad on the phone. 

The award honors teachers who show exceptional teaching skills and inspire their students.

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

Longbranch assistant principal Sommer Kidwell said there’s no teacher more deserving.

“They want to be in her class. They’re excited. In fact, even today, when we said that there was going to be no more teaching or learning, probably going on when kids said, ’Wait a minute, I want to learn something today.’ So that speaks volumes to the engagement and the fun that she brings to the classroom.”

This year Milken will honor 45 educators nationwide. Overall, there have been over 3,000 recipients and over $75 million in prize money. Stewart is Kentucky’s only honoree this year and the Dr. Fletcher said he couldn’t more proud.

Fletcher said, “To be here to celebrate one of our own to win a national award is so important because our profession, again, is the most important. After all, we don’t have lawyers. We don’t have doctors; we don’t have teachers unless we have teachers preparing the way.”

For Stewart, the $25,000 cash prize and national acknowledgment feels surreal, but she said the true magic is the connection she has with her students.

“Beyond the textbooks, beyond the computers. You care about them as a person. And you know you want them to know that you want them to succeed,” she said.

In April 2025, Stewart will join all the other 44 recipients and past winners, in Los Angeles where they’ll get to network and take part in workshops to broaden their impact in kindergarten through 12th grade classrooms. 

Related Stories