The Chester Alumni Chapter evolved from simple conversations to a vision turned into reality by several Kappamen who were raised in the Chester community. On October 18, 1987 this core group of Brothers united to address the social and economic issues facing the City of Chester. On account of their extreme dedication to the Fraternity and the Chester community, these dynamic men moved forward to establish the Chester (PA) Alumni Chapter of Kappa Alpha Psi Fraternity, Inc. on June 25, 1988. The charter members were Carlton B. Adams, Kevin Alexander, Darren E. Alliston, Thaddeus H. Bailey, Jr., Jose Johnson III, Kelvin Johnson, Joseph R. Martin, Calvin D. McNeil, Sr., Virgil N. Perry, Vincent M. Ross, Brian L. Schaffer, and T. David Williams, Jr.

Since the introduction of Chester Alumni in 1988, the members of the Chapter continue to represent the true meaning of "Kappamen" by serving the Chester community with a sustained level of passion. In 1995, with less than twelve active members, Chester Alumni obtained from the Northeastern Province by winning the "Chapter of the Year" Award.

The Chester Alumni Chapter created and continues to maintain a positive presence in the Chester community by demonstrating our commitment through sponsored community events. Some of these events include, but are not limited to, the following: our SAT Prepratory Course, , our our official Kappa League Guide Right Program, Adopt-A-Highway, and Kappa Klassic which provides numerous scholarships to high school students within Chester. Additionally, the proceeds from our annual Turkey Bowl are donated to St. Jude Children's hospital on behalf of the winning chapter, continuing with the fraternity's committment to St. Judes. Other chapter events include the annual Krab Feast, and our annual Winter White party.s