It was during a chance meeting on a Toronto streetcar that OAC President James Mills met Walter Massey (1864-1901) and sought funds from him for buildings required for the growth of OAC, since funding was not available from the provincial government. Coincidentally, three months later on another streetcar, Massey sat next to Mills and announced his family’s decision to provide funds to the school; specifically to build a library. Three months after laying the cornerstone for the building on August 14, 1901, Massey died of typhoid fever. The family’s gift is considered the first private money ever donated to OAC and the first sizeable amount given unconditionally in the Dominion of Canada.

One of Massey Hall’s most popular features was the student coffee house, which was dug out of the basement in just three evenings by OAC, OVC and Macdonald College students. Home to the University’s library until 1968, Massey Hall now functions as a meeting place for students in the drama program.