Oregon Outreach, Inc. (OOI) was formed in 1988 to provide social services to gang-affiliated youth in north and northeast Portland. Programming consisted of pre-employment training and job placement services. However, the need for educational programming became apparent, so the organization registered with the Oregon Department of Education as a school, while continuing to work with juvenile parole and probation offices.

Then, realizing that there were many kinds of students without a school program, OOI established two more satellite schools: Alberta Learning Center for middle school students; and Simpson Learning Center for students with drug and alcohol dependency. In May of 1993, these programs were merged in order to provide more comprehensive services for the students and renamed Gladys McCoy Academy, which serves youth and adults. To help address the needs of other students in various neighborhoods and communities, more satellites were developed. The first satellite opened in May of 1993. OOI now has three programs: Gladys McCoy Academy in NE Portland, Molalla Academy, and Scappoose Academy.

Each school site provides a positive academic experience for each of its students. The majority of students are at risk or outside the traditional school system. Some students need a smaller, more-tailored academic plan to reach their educational goals. By developing a program to suit the specific needs of each student, they are able to graduate from high school and work towards completing their educational goals.