Kimi Kean, Amina Assefa, Charles Cole, and David Silver stand on stage
Charles Cole III, third from left, accepts a mayoral proclamation from David Silver, the deputy director of education for Mayor Libby Schaaf, at the ceremony where he also received the Dirk Tillotson Education Advocate Award from Families in Action. Credit: Families in Action

Sign up for The Oaklandside’s free daily newsletter.

Dirk Tillotson’s death on Oct. 1 last year devastated Oakland’s education community. Tillotson was a fierce advocate for equity in education, especially for Black students. He helped to start charter schools in Oakland and elsewhere, and championed family voice and choice in schools.

In the 14 months since Tillotson was tragically shot and killed during a break-in at his home in Maxwell Park, the organizations and individuals he left an impact on have been finding ways to keep his spirit alive. Families in Action, a family advocacy organization founded in 2019 with Tillotson’s help, began a new tradition this year to honor his legacy. 

“His passing was super devastating for us,” said Kimi Kean, a co-founder and CEO of Families in Action. “One person we work with said, ‘People die when you stop saying their name.’ So we thought to ourselves, how can we keep saying Dirk’s name and remembering what he stood for? What are ways to keep his legacy alive?”

In April, Families in Action announced the Dirk Tillotson Education Advocate of the Year award to honor individuals who embody Tillotson’s values. Kean worked with Tillotson’s wife, Amina, to field nominations and select the winners. During a ceremony in September, Families in Action honored Charles Cole III and Amber Blackwell as the inaugural recipients. The group also established an award for Rachel Willis-Henry, a parent leader who died in 2019.

Dirk Tillotson, 52, was a prominent education activist in Oakland who was shot and killed Oct. 1, 2021. Courtesy Charles Cole III

Cole, who grew up in Oakland, is the executive director of Energy Convertors, an organization that empowers young people to improve their schools by training them in research, advocacy, and community engagement. He’s also written books to help Black boys who are first-generation college students and Black parents navigating education. 

Cole said it was honor, but that it felt strange to receive an award named for his mentor.

“I’m still mourning my friend,” Cole told The Oaklandside this week. “He gave people a lot of hope that I think is still there, and there are a lot of people taking his energy and running with it. I’m just trying to put more good into the world than bad.”

In 2018, Cole and Tillotson, along with former OUSD school board member Jumoke Hinton and fellow education advocate Bennie Patterson, launched State of Black Education in Oakland, a group that hosts events and conversations with families, educators, and other local stakeholders about education equity in the Black community. 

Together with members of that organization, Energy Convertors, and Families in Action, Cole led a campaign in fall 2021 calling on Oakland Unified School District to “Dump the D” and align its high school graduation requirements with the admission requirements for California’s public four-year colleges, to allow more Oakland graduates to qualify for those schools. An Energy Convertors report found that during the 2019-2020 school year, only 35% of Black students and 47% of Latino students attending district and charter schools in Oakland had completed the class requirements for UC/CSU admission when they graduated. 

Blackwell received the award’s honorable mention distinction. She serves as the executive director of Higher Ground Neighborhood Development Corporation, a nonprofit organization she initially founded in 2002 to operate a charter school. The charter school didn’t work out, but for 20 years, Higher Ground has worked with district and charter schools to provide tutoring, after-school and summer programs, and other student-enrichment activities. 

Amber Blackwell and Charles Cole joined by Tunisia Harris and Mario Rodriguez, who received awards honoring parent leader Rachel Willis-Henry. Credit: Families in Action

Blackwell met Tillotson in the 1990s when they were both part of the movement to establish charter schools in Oakland. 

“We aligned on education being a revolutionary act, because we weren’t on the side of reform anymore,” Blackwell told The Oaklandside. “We were kind of fed up with school reform and we wanted revolution, which was a total change and overhaul in the way our children received education in Oakland.”

Blackwell and Cole praised Tillotson for his veracity, his willingness to engage with people on all sides of an issue, and his emphasis on uplifting family and youth voices—qualities they strive to maintain in their work. 

“He lent some very valuable expertise to a place where people didn’t always do that,” Cole said. “We saw a lot of people purposely make things confusing or convoluted. What we tried to do the most as a team was to take the complicated and make it accessible. That’s what made him unique.”

Another Oakland education organization that Tillotson had a hand in starting was Ledbetter, formerly called Great School Choices, which helps develop and sustain small charter schools and advocates for school choice. Paul Le had helped Tillotson run the organization, and he became its executive director after Tillotson’s death, moving to Oakland from New York City this past summer to continue the work. He also took over Great School Voices, Tillotson’s blog where he published his critiques and examinations of Oakland’s education system.

While Le admits that he can’t replicate Tillotson’s voice or breadth of knowledge, he is working to maintain aspects of the blog that were important to Tillotson, like lifting up community voices. Last month, the blog published a series of interviews with Oakland school board and mayoral candidates who answered questions submitted by students. By 2024, Le wants youth who won the right to vote in future school board elections to be able to use Great School Voices as an information resource. He plans to continue Tillotson’s work of publishing content urging OUSD to make progress on issues of literacy, school safety, governance, housing, and educational inequities. 

“We owe it to the kids and families and community organizations who looked up to him [to continue the blog],” Le said. “I moved here from New York City because of that movement he created. You can’t do that from another coast. I’m inspired, not just by him, but by what other folks in the community have done to push that mantle even further than he probably imagined.”

Charles Cole poses with Amina Assefa, Dirk Tillotson’s wife. Credit: Families in Action

Tillotson was fatally shot during a home invasion and robbery on Oct. 1, 2021, in the home where he lived with his family in Oakland’s Maxwell Park neighborhood. Nearly 15 months later, the Oakland Police Department has not made any arrests or released any suspect information in the case.  

Families in Action will open nominations in the spring for the next Dirk Tillotson Education Advocate of the Year. Kean, the organization’s co-founder, said she plans to continue to work with Tillotson’s wife to winnow the nominations.

“For someone like Dirk, to know that he’s not forgotten or lost but that there are real concerted efforts to keep his legacy alive, that really resonated with (Amina),” Kean said. 

Ashley McBride reports on education equity for The Oaklandside. She covered the 2019 Oakland Unified School District teachers’ strike as a breaking news reporter for the San Francisco Chronicle. More recently, she was an education reporter for the San Antonio Express-News where she covered several local school districts, charter schools, and the community college system. McBride earned her master’s degree in journalism from Syracuse University, has held positions at the Palm Beach Post and the Poynter Institute, and is a recent Hearst Journalism Fellow.