Press Releases

2018 2017 2016 2015

KIPP DC College Prep Principal Flabbergasted at Winning a Milken Educator Award & $25,000 during School Assembly

October 8, 2015

SANTA MONICA, CA — The principal, teachers, staff and students at KIPP DC College Prep thought the highlight of the morning assembly was the official opening of the renovated high school. They had no idea the real reason for the schoolwide gathering was to honor their principal, Jessica Cunningham, with a Milken Educator Award and $25,000.

Cunningham was shocked when she accepted her navy blue envelope from Milken Family Foundation Chairman and Co-Founder Lowell Milken. For the next six months, in up to 40 schools around the U.S., outstanding middle and high school educators will be given the surprise of a lifetime when they receive a Milken Educator Award and an unrestricted cash prize of $25,000 before cheering students, respected colleagues, distinguished officials and the media during a boisterous assembly.

Milken said Cunningham, who is the first recipient of the 2015-16 school year, is a special principal.

“Jessica has been identified as one of KIPP’s top educators,” said 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.”

“To put it in sports terms, Jessica Cunningham is our franchise quarterback or our closer,” said KIPP Founder and CEO Susan Schaeffler. “She not only leads and prepares our high school students for college, but she also inspires our entire KIPP DC region to care more and do more because of her excellence. She knows that our students’ futures depend on what we do today and she is in it for the kids, with the kids, year after year.”

Success in the classroom and natural leadership ability led Jessica Cunningham from teaching to becoming the principal of KIPP DC College Preparatory (KCP) in 2012.

Under her leadership, KCP has become the highest-performing open-enrollment high school in Washington, D.C. The school’s proficiency rates on DC CAS (Comprehensive Assessment System) increased by 19 points in math and reading during Cunningham’s tenure, with 20% of students enrolled in the special education program. In 2014, the school posted a math proficiency rate of 95% and a reading proficiency rate of 71%. The graduation rate is 99% and the college matriculation rate is 89% for 2013 and 2014.

KIPP DC is part is a national network of 183 free, open-enrollment public charter schools with a track record of preparing students in underserved communities for success in college and life. KIPP schools incorporate a longer day and a commitment to incentivizing students to attend and complete college.  KIPP four-year college graduate rate is above the national average for all students and four times that of students living in poverty.

“Jessica Cunningham, the outstanding principal of KIPP DC College Preparatory Public Charter School, stands out as a model to her colleagues and a source of inspiration to her students,” said D.C. State Superintendent of Education Hanseul Kang. “Her passion for education and dedication to the students she serves have had an immediate and noticeable impact on academic achievement. For these reasons and many more, I enthusiastically applaud Principal Cunningham's tremendous achievement and wish her the best.”  

Cunningham, whose mother was a teacher, is respected by students for telling them the truth, holding them accountable and suggesting helpful practices to help them grow as young people.. She identifies with them and likes to provide opportunities for the students, many from challenging backgrounds, to make a fresh start. They see her as someone they aspire to be.

College readiness is a priority for Cunningham, who invites guest speakers in to inspire career goals. When the high school opened, the average ACT score was 16.9. It is now 18.9. She gets parents and other family members involved.  When students are not performing up to expectations, she is quick to call their parents. Cunningham also works closely with the college counseling team to ensure students partake of scholarship opportunities.

Cunningham has been a part of the KIPP system for 11 years. She started out as a teacher and then became the founding principal of KIPP DC WILL Academy, the third KIPP middle school to be established in the District. WILL Academy had the highest overall growth of all DC charter schools in 2009-2010. All eighth grade students attended a top choice high school.

An Aspen Scholar, Cunningham is a role model to fellow educators. She develops curriculum and delivers professional development as part of the KIPP Foundation’s School Leadership Program. She informally mentors several school leaders around the country and coaches KIPP national administrators.

Cunningham graduated with a Bachelor of Science in African-American history from Florida A&M University in 2000 and a Master in Education from American University in 2003.

The Milken Educator Awards, which was launched by the Milken Family Foundation in 1987, has been described as “the Oscars of teaching” by Teacher magazine. Recipients are selected in early to mid-career for what they have achieved and for the promise of what they will accomplish. Many have gone on to earn advanced degrees and be placed in prominent posts and on state and national education committees.

Alternating yearly between elementary and secondary educators, the Milken Awards are sourced through each participating state department of education, which appoints an independent blue ribbon committee to confidentially review candidates for recommendation to MFF.

This year, MFF is launching a #MyTeacherRocks Instagram campaign that encourages students to take selfies with their favorite teacher and describe in the caption why their teacher is special. To enter the contest, entrants are asked to follow @milkenfamilyfdn on Instagram, post their selfie to their individual account and use the #MyTeacherRocks and #MilkenAward hashtags. The three photos with the most “likes” will be selected in November 2015, and February and April 2016. The winners will each receive $500 for their classroom.

To get regular updates on the surprise Milken Educator Award events, follow and use the #MilkenAward hashtag on Instagram, Facebook and Twitter.

For more information about the Milken Educator Awards, visit or call MFF at (310) 570-4772. 

The Milken Educator Awards tour is on social media at:

The Milken Educator Awards, created by the Milken Family Foundation, were launched in 1987. The Awards provide public recognition and individual financial rewards of $25,000 to elementary and secondary school teachers, principals and specialists from around the country who are furthering excellence in education. Recipients are heralded in early to mid-career for what they have achieved and for the promise of what they will accomplish.

Ana Beatriz Cholo
Media Relations Manager
310-570-4773 (Office)
312-927-4845 (Cell)
Twitter: @AnaBeatriz_MFF