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Union teacher surprised with ‘Oscars of teaching’ award, $25,000 prize

Jenna Stewart receiving her award
Teacher Jenna Stewart stands with her class
Jenna Stewart celebrates with her students
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UNION, Ky. — Jenna Stewart had no idea that, when she went to Longbranch Elementary’s school gym on Wednesday morning, she was about to win an award related to the “Oscars of teaching.”

Then her name was called, cheers erupted and cameras flashed as she came forward to accept the national award, which comes with a $25,000 prize.

Teachers, district administrators, students, reporters and state leaders—including Kentucky First Lady Britainy Beshear and Kentucky Commissioner of Education Robbie Fletcher—packed the Union school gym on Wednesday morning to celebrate the fifth-grade teacher.

Called the Milken National Educator Award, the recognition traces back to Lowell Milken, a California-based businessman and philanthropist who founded the Milken Family Foundation in 1982.

The award recognizes excellence in education; this year, 45 educational professionals across the country were honored. Jane Foley, the senior vice president of the Milken Educator Awards (and a previous recipient of the award), spoke at Wednesday’s event. Stewart was the only recipient from Kentucky this year.

The foundation does not accept nominations, and there’s no application. Winners are selected through a secret process and reviewed by state blue-ribbon panels.

“We recognize excellence in other professions,” Foley told the students. “Think about it… athletes have Most Valuable Player awards. Entertainers have Golden Globes and Oscars. In science and medicine, Nobel Prizes. But our educators, who have the most important job of all—they are teaching the people who are getting all the other awards; they’re teaching all of you—they don’t have that kind of celebration. That’s just wrong. And the people at the Milken Foundation set out to change that.”

After more remarks, Foley read Stewart’s name from a navy blue envelope, Academy Awards-style. Cheers from the students and flashes from reporters’ cameras erupted throughout the gymnasium as Stewart rose from her seat to accept the award.

Stewart has been teaching for 11 years, nine of which have been at Longbranch. She graduated from the University of Kentucky in 2014 and is pursuing a master’s degree in counseling at the University of the Cumberlands.

Her students have achieved 90% proficiency or higher on state benchmarks. She co-chairs the district’s Student Job Committee. She also hosts so-called porch pop-ins at students’ homes at the beginning of the school year, where she encourages them to do their best in the upcoming year.

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

Stewart also spoke about the importance of fostering deep relationships with her students.

“I want to get to know them beyond the campus,” Stewart said. “I want them to see that they’re capable of doing anything.”

Stewart celebrated with her students at the end of the ceremony. She and other award winners will travel on an all-expenses-paid trip to Los Angeles in April to receive their monetary awards and celebrate at a red carpet event. Stewart can spend the money however she chooses.