Usually, when officials from the California-based Milken Family Foundation show up at school, everyone who knows anything about their surprise visits starts wondering which teacher will be honored for his or her outstanding accomplishments.
However, when the honoree was announced earlier this month (Oct. 8) during an assembly at KIPP D.C. College Preparatory College in Northeast, the person who’d least expect to be called out was none other than the principal.
“I feel shocked and grateful,” said Jessica Cunningham, who thought she was attending a ribbon-cutting ceremony. “I really had no idea this was happening today. I thought it was going to be a (short program), send the kids back to class, and then a few meetings. But nothing like this.”
The honor, touted by “Teacher Magazine” as the “Oscar of Teaching,” comes with a $25,000 unrestricted award.
Cunningham was the first educator this year to receive the prestigious award, which will be given over the next six months to educators at more than 40 educators across the country.
The recipients – in the early to middle levels of their careers – are selected based on for what they’ve achieved and the promise of what they’ll accomplish.
Cunningham, who prides herself on preparing her students for college, ranks among the 2,600 people who’ve received the Milken Educator Award since it was first given in 1987.
“Jessica has been identified as one of KIPP’s top educators,” said Milken Family Foundation chair and co-founder Lowell Milken. “She is a teacher leader who takes very seriously her mission to ensure her students are prepared to compete in high school, college and, ultimately, the workplace.”
Cunningham, who’s been part of the KIPP system for 11 years, began her career as a teacher before going on to become the founding principal in 2012 of KIPP DC Will Academy – the third KIPP middle school to be established in the District.
In addition to serving as a role model to her fellow educators, Cunningham mentors several school administrators and other academic leaders across the country and still finds time to coach KIPP’s national administrators.
Due to Cunningham’s efforts, KIPP Prep currently lists as the highest-performing open-enrollment high school in D.C.
When KIPP Prep opened, the average ACT score was 16.9 and has since elevated to 18.9. Cunningham, who’s an Aspen Scholar, has also been instrumental getting parents and other family members involved in their children’s education.
Hanseul Kang, whose Office of the State Superintendent of Education describes Cunningham an administrator highly respected by her students, added that she stands out as a source of inspiration to them as well.
“Her passion for education and dedication to the students she serves has had an immediate ad noticeable impact on academic achievement,” said Kang, who also referenced increases in student graduation and college acceptance rates – which KIPP Prep officials boast respectively at 99 percent and 89 percent.
Cunningham, herself, graduated in 2000 with a Bachelor of Science degree in African-American history from Florida A&M University, and a master’s in education in 2003 from American University.