The Confucian private academies or sŏwŏn of Chosŏn Korea (1392-1910) enjoy an imputed legacy of having been educational institutions of venerable age, serenely situated in rural locales in which Neo-Confucian metaphysics was studied and transmitted by wise masters. The reality was more dynamic and distinctly grittier: the academies were born in an age of growing political despair in the mid-sixteenth century and ended in wholesale violence as the sŏwŏn system was largely destroyed between 1868-1871 by the Taewŏn’gun. This paper examines the unlikely constellation of events that led to the creation of the first sŏwŏn in Chosŏn Korea, the Paegun-dong Academy in 1543 in the remote mountainous county of P’unggi, Kyŏngsang-do and its subsequent royal chartering in 1550 as Sosu Sŏwŏn. Chu Sebung (1495–1554) and Yi Hwang (1501–1570) were the pivotal figures in these events, as in separate ways they sought to comport their growing fascination with the social and moral implications of Southern Song learning from the twelfth century with their own trajectories of ambition and frustration as local magistrates. From the outset the sŏwŏn were less pristine academies dedicated to immersion in philosophy and more local institutions serving a diverse set of worldly interests in their locales.