Macalester’s Old Main was built later than most, with the East Wing constructed first in 1883.¹ A competition was held among architects for who would get to design the college’s first building. Multiple designs were considered, however it was the firm of Willcox and Smith who cinched the final deal.² In the East Wing, the basement held the communal dining room, the first floor housed the chapel and several classrooms, and the second and third floors were devoted to housing for students.³

The construction of the West Wing followed in 1887, giving the college a new reading room, several more classrooms, and a basement gymnasium. However, building the West Wing also added a significant amount of money to the college’s hefty debt, which added up to around $125,000 by 1889. Although the Board of Trustees had recently committed not to spend any more money on new construction, they still decided to approve the addition of the West Wing to the college’s main building for $68,000, $48,000 of which was borrowed money.⁴

This mounting debt posed a significant challenge for the school. Henry Daniel Funk, a Macalester professor in the early 20th century, wrote in his short history of Macalester that at this point, “the college was so impoverished that its future seemed absolutely hopeless.”⁵ After an ambitious fundraising campaign, the college managed to raise enough money to stay open for the 1891-92 school year, but ran into more trouble with the Panic of 1893. It wasn’t until the early 1900s that the college was able to find firm footing. Disaster was only thwarted when Mrs. William Thaw, the widow of a Pennsylvania philanthropist, purchased several acres comprising the bottom of campus for $25,000.⁶ The land was eventually deeded back to the school ten years later.⁷ By the time he was writing his history of the college in 1910, Professor Funk expressed sincere relief that the college had been able to survive the financial turmoil of its early years.