Our Anniversary

For 20 years, The Fund has worked alongside educators to redefine what it means to be a leader in Chicago’s public schools.


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The 2020-21 school year marked 20 years of our investment in Chicago public schools.

Throughout the year, we shared stories from The Fund’s history, hosted events to celebrate our city’s outstanding school leaders, and highlighted some of the amazing things happening in our schools.

To read more about the amazing educators we worked with this year, look at the posts marked 20th Anniversary on our blog. Otherwise, look below for highlights of our school leaders, events and reports.

By the Numbers










BLOG | Omar Chilous

The Fund explored the powerful legacy of Social Justice High School located in Little Village, and how Principal Omar Chilous is leading his students to turn passion into action.


BLOG | Maria Amador

The Fund profiled Maria Amador, principal of Multicultural Arts High School, and talked about the prioritizing the arts, meeting the needs of diverse learners and giving all MAS students PRIDE.

BLOG | D’Andre Weaver

The Fund interviewed D’Andre Weaver, a former Chicago principal who now serves as Superintendent of DeSoto ISD in North Texas and as a Fund Board member.

EVENT | Resilience: A Night of School Leader Stories

In October 2020, on this storytelling night, school leaders shared their stories of personal strength before and during the pandemic.

EVENT | Leading Toward Tomorrow

In May 2021, this panel centered how leaders everywhere have reimagined the roles that they play given COVID-19 and the global fight for racial justice.

EVENT | Return to Learn: Reopening Tools and Best Practices for CPS School Leaders

On November 2020, The Fund partnered with Easterseals Chicago to host a panel about includes tangible resources and best practices for reopening schools for pre-k and cluster program leaders.

REPORT | COVID-19 Comeback Fund Case Studies

This report examines nine case studies about how Chicago principals used grants of up to $10,000 to meet the immediate needs of their communities, while also innovating for the future.

REPORT | Chicago Principals Overview

This report provides of snapshot of district school leaders during the 2020-21 school year, including demographics, position tenure, turnover rates and more.

REPORT | Budget Case Studies

This report features four case studies on the innovative budgeting practices of principals in district-operated schools.

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