Benjamin Louwrens Osler was born in Aliwal North in the Cape Colony on 23 November 1901, during the Anglo-Boer War. He received his education at Kingswood College in Grahamstown (now Makhanda) and Rondebosch Boys' High in Cape Town. He was a keen student and rugby player, and a perfectionist at everything he did. While working as an attorney in Cape Town, Osler used to visit Newlands Stadium to practise his kicking, running and side-stepping. He became highly adept at kicking with both his right and left foot, a great asset for a fly-half.
He was chosen to play in this position