The earliest case he recounted in his autobiography concerned a bequest to the City of Philadelphia by Benjamin Franklin in 1790, which was to fund interest-bearing loans to deserving artisans. Newly minted lawyer Pepper lost the case brought on behalf of Franklin's heirs in 1890, but learned "in any human system for the administration of justice there must be a reserved judicial right to refuse in exceptional cases to stretch beyond the breaking point a legal principle that is sound enough for everyday use." Five decades later, the Orphans Court (which was found to lack jurisdiction in the original case) appointed him Master to determine question under Franklin's will and thus facilitate the administration of the trust which as a youthful advocate he had tried to set aside.