The Winchester Education Foundation was established as a non-profit educational foundation, separate from the Handley Board of Trustees, in 2000 under the leadership of former Superintendent of Winchester Public Schools Glenn Burdick.   The original objectives of the organization were to generate money for scholarships for faculty enrichment and for students planning to become teachers and to handle special gifts to the school system from private donors.  The first donation received was a $10,000 anonymous contribution to improve the track at Daniel Morgan Middle School.

In 2004, the WEF was re-organized to its current structure under the leadership of Richie Pifer, Harry Smith and other community leaders.   This structure created a partnership between the Handley Board of Trustees, which saw the need to supplement the diminishing trust fund originally bequeathed by Judge John Handley, and the Winchester Public Schools for the purpose of private fund-raising, with two additional organizations with strong ties to Handley High School also joining in:  the Judges Athletic Association and the John Handley High School Museum and Archive.

The four organizations believed that together their fund-raising efforts could be more streamlined, efficient and successful.   The structure called for each member organization to appoint one to three representatives to serve on the WEF board of directors.  A ninth director was later added, selected at-large by the current WEF directors.

The WEF’s purpose is to enhance the funding resources of the Winchester public schools above and beyond local and state funding.  Money raised is not solely for the benefit of John Handley High School but benefits all the schools in Winchester.

The WEF stood down in its fund-raising activity during the capital campaign for the renovation and expansion of Handley High School from 2005 to 2009 in order not to compete with those important fund-raising efforts.   In 2009, under the leadership of Damon DeArment as board president, the WEF became revitalized as a fund-raising entity and hired the capital campaign’s very successful fund-raiser, H. Russell “Russ” Potts, Jr. to become the WEF executive director and to spearhead fundraising efforts on its behalf.