Theo Pienaar, born in 1888 in Barrydale, left a lasting mark on South African rugby. Educated in Somerset West and Victoria College, he earned a teaching diploma before excelling as a player and leader. Pienaar captained Stellenbosch, Malmesbury (leading them to the Grand Challenge Cup in 1915), Caledon, and Western Province, with whom he played from 1914 to 1922.
In 1921, at age 32, he became the first Springbok to debut as captain during the tour to Australia and New Zealand. However, an injury prevented him from playing in the test matches, and Boy Morkel stepped in as captain. Despite this, Pienaar played 10 tour games, demonstrating his resilience and leadership.
Beyond playing, Pienaar served as a South African selector (1928–1931) and managed Bennie Osler’s 1931–32 Springbok team, achieving a Grand Slam in Britain and Ireland. His contributions on and off the field highlight his profound influence on South African rugby history.