Teacher stands talking to students


In 1988, Susie Gillespie, the daughter of Pittsburgh philanthropist Ed Ryan, approached the city's Catholic grade schools to ask how she might assist them and their student body. The principal of St. Agnes School in the Hill District asked for financial assistance so that one of her brightest eighth-grade students could attend Central Catholic High School rather than the underperforming public high school in his neighborhood.

Ms. Gillespie not only honored this request but also inquired with the city's other Catholic grade schools about how she could support them as well. As a result, twenty-one students, who might not have otherwise been able to afford to attend the local college-preparatory Catholic high schools, were given financial support to enroll in these institutions, ushering in Crossroads’ inaugural 1988-89 academic year.

Almost immediately, these students found themselves struggling to keep up with an academically demanding course load while adjusting to a new social environment. It became clear that for Crossroads scholars to truly succeed, assistance beyond a “dollar amount” would be necessary. Out of this need, Crossroads decided to hire tutors and on-site counselors, a move that sparked the eventual development of our four-part student model.

After working out of "classrooms and car trunks" for our first ten years, Crossroads Foundation formed a Board of Directors in 1998, obtained our 501c3 status in 2003, and established our first office in a former rectory in the Hill District in 2006. 

Click on the timeline below to learn more.

Esther walking down hall with scholars

Crossroads Today

Over the last several years, Crossroads has experienced significant growth and expansion of the number of students we are able to serve and the level of programming we are able to offer our families.

Now in our 35th year of operation, our student body stands at 160 scholars across all classes, and we have graduated over 650 scholars since 1988 — over two-thirds of whom have gone on to earn college degrees.

As our student body grows, Crossroads continues to expand programming based on scholar needs, while addressing our core mission: paving equitable and accessible pathways to success for young people by helping them meet their academic potential and achieve their long-term goals.