Gwendolyn Diggs

Gwendolyn Diggs chats with the kids during their lunch at the Urban League Head Start program on Monday, Oct. 4, 2021. 

Gwendolyn Diggs has spent the past 26 years following her calling to work on education, educating children of all ages throughout those 26 years. She has worked in administration in Jennings School District, Ferguson-Florissant School District, and the National Institute for School Leadership in Washington, DC.

On Friday, November 5, Diggs will receive the 2021 Stellar Performer in Education Award at the St. Louis American Foundation’s Salute to Excellence in Education Scholarship and Award Virtual Gala.

In addition to the celebration of our outstanding educators, the foundation and its partners will award over $2 million in education grants and college scholarships to high-potential, local students of color during the virtual gala.

Diggs began her most recent role as the vice president of Head Start/Early Head Start for the Urban League of Metropolitan St. Louis in 2019. That means she has spent a large portion of her tenure there helping very young children — some of them too young to even be asked to wear masks regularly — begin to grow up during COVID-19. 

And supporting those children, for Diggs, means supporting an entire community. As the pandemic began, she said, “It was very important to make sure that I considered all individuals.  It didn't matter if they were staff, students or parents or families and the community. So I wasn't isolating any individual group, but it was taking care of everyone as best I could.”

Her leadership during this period has already earned her a 100 Most Inspiring Saint Louisans Award and the PNC Lift Up St. Louis award, as she guided the Urban League’s Head Start centers, which are funded to serve a total of 931 students, through total shutdown, into virtual learning, and back into fully-in-person operation while complying with CDC standards. Working to make sure the 184 staff members at all the centers had what they needed was also critical, Diggs said: “All of our teachers now have laptops, even those positions that are outside of the classroom.” 

During the months in which all Head Start and Early Head Start centers were closed, Diggs also facilitated the distribution of Hatch tablets — educational tablet devices to help young children with image recognition and reading comprehension — to all Head Start students. 

Now, as all the Head Start centers are in fully in-person operation again, Diggs is confident that her team has the skills to go back to remote learning and support parents in doing so, should that become necessary. While the number of children enrolled at the centers is still a little bit lower than normal thanks to families’ anxieties about COVID, Diggs looks forward to drawing families back in by working with her staff to improve curriculum. 

Diggs credits her success in part to mentors like Dr. Art McCoy, who she worked with while serving in administration at Jennings, and Michael McMillian of the Urban League. 

She began her career as a classroom educator, and “saw a lightbulb go off”: teaching kids and watching their learning and confidence progress was what she loved to do. Then, the lightbulb went off again, and she realized that by moving into administration, she could spread that love for children at a wider scale.

“If I can help 20 kids in a classroom, I could have more kids if I was in a different position,” Diggs said. “So at that point I started pursuing my administrative certification, because I love seeing kids learn At Jennings, “Dr. McCoy and his leadership was very eye opening for me,I just looked at him as a stellar  educator and mentor,” she said. 

“It's that eagerness or that hunger to make sure that I'm pouring into kids everything that I can pour into them,” Diggs said. Lately, she’s been focusing that eagerness on STEAM education for her very young students: making sure that their introduction to ideas around creative scientific and artistic thinking doesn’t just start in elementary or middle school. 

“I don’t want them to just wait until they are getting into kindergarten or third grade or eighth grade or middle school,” she said. “Having that exposure early is just to increase their motivation to want to learn more in that field.” To achieve that early exposure, Diggs has set up partnerships between the Urban League’s Head Start program and various local institutions such as Washington University, PNC Bank, and Maryville University. 

In her work at the Urban League so far, Diggs is most proud of the feedback she’s gotten from parents and community members. “Just hearing from someone else that something that I have done has made a difference for them. And that can be different every day, you know, just knowing that my efforts made a difference in their lives,” she said. 

Diggs is a member of Delta Sigma Theta Sorority, Inc., and a regular volunteer at Urban League programs even outside of the Head Start sphere. 

The 34th Annual Salute to Excellence in Education Scholarship & Awards Virtual Gala will be celebrated online as a free virtual event on Friday, November 5, 2021, on, the St. Louis American’s Facebook page and YouTube channel. For additional details on how to participate, please visit

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