After school and a stint in the merchant navy training academy The General Botha at Gordon's Bay in the Western Cape in 1952–53, McGregor enrolled at the South African College of Music, then headed by Professor Eric Chisholm. Here McGregor was exposed to a different set of influences, during the day Béla Bartók and Arnold Schoenberg, and at night recordings of Duke Ellington and Thelonious Monk, and the live music of local jazz musicians such as Dollar Brand (now Abdullah Ibrahim), Cecil Barnard (now Hotep Idris Galeta), Christopher Columbus Ngcukana, Vincent Kolbe, "Cup-and-Saucers" Nkanuka, Monty Weber, the Schilder brothers, and many others who were active in the vibrant Cape jazz scene at that time, the mid-1950s. The vibrancy and power of this music has led some to designate the music played around Cape Town as a particular jazz genre called "Cape Jazz." (Miller, 2007).