For drama teacher Jessica Winingham, every professional development day, every meeting and every school-wide event at Lindbergh was the same. While the roster of attendees may have varied from function to function, they were always completely, undeniably white. Many of Winingham’s coworkers brushed her off as an “other,” or simply ignored her entirely. But when a question was brought up about inclusivity efforts, everyone in the room would turn to look at her.

Winingham spent 13 years as one of the few people of color teaching at Lindbergh High School. Now, as the new head of Ladue High School’s theater department, she is taking steps to ensure that no student experiences the same level of isolation.

“I never want anyone to feel marginalized in my room,” Winingham said. “I always want people to feel like they can be their authentic selves. And that comes from a place of being in positions throughout my life where I was not encouraged to be that way.”

Winingham grew up in a household that embraced the performing arts. In fact, some of her earliest memories involve watching film adaptations of popular Broadway musicals.

“I was in a play for the first time when I was 8 or 9 at a community college, and then I was in The Muny when I was 9,” Winingham said. “And then after that, I was kind of obsessed. So I just did theater forever after that, and then all throughout school.”

Winingham pursued the dramatic arts long after high school and graduated from the University of Missouri with a Master’s Degree in Secondary Education in 2011. As of 2020, she is in the process of earning a second Master’s Degree in Theater Studies in Production and Design at Southern Oregon University.

Before Winingham knew she wanted to pursue education, she was a professional actress. Most notably, she headlined the feature film “Four Color Eulogy” in 2014. However, she describes her transition from exclusively acting to teaching as “really organic.”

“I enjoy watching students grow in their art form much more than I need the validation of being in it,” Winingham said. “I love performing, don’t get me wrong. I’m a performer. I love attention. We all do. But my cup is filled much more from watching students than from me.”

Winingham’s potential as an educator was first discovered in 2004. At the time, she was performing in William Shakespeare’s “Troilus and Cressida,” with SLIGHTLYaskew Theatre Company, a program that she co-founded.

“Two women, who were seniors [from the Yale theater department], came to see our show, and then came up to myself and Meryl, who is the other woman that created the company with me, and said, ‘We would like you to teach a workshop at Yale,’” Winingham said.

The course in question covered a form of South American theater technique, which Winingham led in winter of 2004 when she was in her 20s. Since then, she has lent her wisdom to performing arts departments such as the Center of Creative Arts and University City High School.

After over a decade spent at Lindbergh, Winingham was hired as the director of Ladue High School’s theater department in 2023. Her first production at Ladue, “Puffs,” is set to premiere Oct. 26 in the Performing Arts Center.

Winingham cares deeply about creating an environment in which students can feel comfortable. The cast of her most recent play is composed of 25 students, including junior Madison Davidson, who plays various roles that mirror well-known characters from the “Harry Potter” franchise.

“I feel that Ms. Winingham strives for diversity,” Davidson said. “She makes it clear that she wants a comfortable space for [everyone] and doesn’t want anyone to be [discriminatory] against people.”

For many cast members, it was their first time auditioning to be a part of a theatrical production. In order to curate a supportive space for newcomers to let go of their nerves, Winingham acted as a warm and encouraging presence in a cold, black room.

“Going into the audition, she made sure everyone felt like they did an amazing job,” senior Jessica Steinberg, who portrays Sally Perks in “Puffs,” said. “That was something that I haven’t felt ever before from a director.”

A lot can change following a show’s final performance, but one factor will forever remain consistent in Ladue’s theater department: under Winingham’s jurisdiction, the curtain will never close on community-building.

“I love how theater is so ensemble-based,” Winingham said. I love [how] every show you make a family, and you invest in that family, and then it disappears.”

To listen to an interview with Jessica Winingham, click here.