Charles Stockley spent his early years in Delaware, where he taught school and operated a general store before focusing on farming and peach growing. He gained significant experience in public service, serving as Sussex County Treasurer and Sheriff, and later as a state senator, including a term as Speaker. Stockley transitioned into banking and railroad management, holding leadership roles in several financial and transportation institutions. His career culminated in a governorship marked by efforts to reduce tariffs, expand the state legislature, and advocate for separate schooling for black children, alongside noting improvements in African American enfranchisement.

Charles Stockley's political identity is marked by a blend of traditional and progressive elements, particularly in his stance on civil rights and education. He opposed tariffs while advocating for the expansion of the state legislature, showing an ideologically agile approach. His support for educating black children in separate schools, coupled with his observation of diminishing prejudice against African American enfranchisement, reveals a nuanced and calculated strategy on racial issues. This juxtaposition of positions suggests Stockley's efforts to balance regional economic interests with evolving social norms.