Neill’s first endeavor in education was the establishment of the Baldwin School in 1853, a preparatory academy financed by Matthias W. Baldwin of Philadelphia.¹ The Baldwin School was built upon a philosophy of gender-segregated secondary education, although in practice, limited financial resources meant that male and female students often learned side-by-side in the same classes.² These limited resources, combined with the turbulent times in Minnesota during the lead-up to the Civil War culminated in the closure of the first iteration of the Baldwin School by 1861.³

Neill had also worked on early efforts to establish the University of Minnesota, becoming its first chancellor in 1858, but continuing financial issues led him to resign in 1861.⁴ The university would not open again until 1867.⁵

The emergence of the Civil War further derailed Neill’s plans for establishing an educational institution. Neill worked as a chaplain in the Union Army, then as a secretary for Abraham Lincoln before spending time abroad, but by 1871, Neill was back in Minnesota and back at work.⁶ He reopened the Baldwin School in 1873, in a former hotel called the Winslow House. The Baldwin School rented Winslow House from Charles Macalester, a Philadelphia businessman.⁷ The building had previously served as a summer destination for wealthy Southern planters (and likely slave owners), but with the outbreak of Civil War, its clientele could no longer take carefree vacations up north.⁸ After the war, the building was simply not ideal to house a school, with too many rooms that were difficult to keep warm, and dangerous structural problems.⁹ However, it was still worth something, and in 1873, Neill was able to convince a reluctant Macalester to set aside Winslow House in his will in order to found a college in his name. In a stroke of luck, Macalester died only a couple of months later, and all of a sudden, Neill’s dream of a college finally seemed within reach.