History
IMPACT FROM THE START
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.
Crossroads Timeline
1988
Crossroads Foundation is founded by Susie Gillespie — daughter of Pittsburgh philanthropist, Edward Ryan — in order to send a handful of promising students with limited educational options to rigorous Catholic High Schools in the Pittsburgh area.
1989
Crossroads and St. Vincent College collaborate to hold the inaugural St. Vincent Week program, kicking off a decades-long partnership to support college readiness for Crossroads scholars.
1990
Total enrollment at Crossroads exceeds 50 scholars.
1991
Crossroads hires its first counselor in order to respond to scholars' individual needs and potential obstacles they may encounter.
1992
The inaugural class of 11 scholars graduates from the Crossroads program.
1998
Crossroads establishes a Board of Directors.
2001
Total enrollment at Crossroads exceeds 100 scholars.
2003
Crossroads officially obtains its 501(c)(3) status and is recognized as an official non-profit organization.
2006
After working out of "classrooms and car trunks" for the first ten years, Crossroads establishes its first office in a former rectory on Webster Avenue in the Hill District in 2006 — the first "Crossroads Center".
2007
Crossroads launches its first endowment campaign, raising over $5 million to diversify enrollment services and programming.
2011
A partnership with KEYS AmeriCorps is established to hire full-time, in-school tutors for scholars in need of academic assistance.
2012
Crossroads triples its number of feeder elementary schools.
2013
Crossroads' current six host high schools are solidified: Our Lady of the Sacred Heart (OLSH), Central Catholic, Oakland Catholic, Seton LaSalle, Serra Catholic, and Bishop Canevin.
2013
Crossroads commemorates the 25th anniversary of its founding.
2014
The LEAD Program (Lead, Empower, Advocate, Discover) for outstanding upperclassmen scholars is established.
2015
Crossroads launches its "Aspire" campaign to increase the endowment to $10 million to expand and enhance programming and scholar services.
2016
Crossroads moves into its current student-centered space, the Calland Center, located in historic Homewood.
2016
In celebration of graduating our 500th scholar, Crossroads establishes the "500th Fund" to support first-year alumni as they transition to college.
2017
Crossroads completes a second strategic planning session, identifying six pillars for future growth with the goal of stewarding the organization into its fourth decade of being a regionally impactful organization.
2018
A group of parents with purpose establishes the Parent Leadership & Advisory Council (PLAC) to offer advice and assistance to Crossroads staff regarding program priorities, and to serve as support for other parents in addressing larger community and family needs.
2020
In partnership with F.A.M.E, Higher Achievement, NEED, and the Neighborhood Academy, Crossroads co-launched the Pittsburgh College Access Alliance (PCAA), which is committed to increasing preparation for and access to higher education pathways for Black students in Pittsburgh and the surrounding areas.
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.