In 2009, Leonard would leave a freelance career and rejoin the Fathead band. Teddy performed with blues musicians from Canadian and International destinations on the short list such as Eddie Shaw, Carey Bell, Fenton Robinson, Luther 'Guitar Junior' Johnson, Snooky Pryor, Big Jay McNealy, Honkin' Joe Houston, Phil Guy, Johnny V Mills and Cash McCall. They provided upcoming musicians the opportunity to perform with a working band then, when International and Canadian blues musicians came to town to play the Black Swan they had the Kendall Wall Band backing them up. The Kendall Wall Band arrived at a time when it was a crucial period for blues music in Canada, let alone in the city of Toronto. This created the opportunity to perform with some of the well respected in blues music in Canada and Internationally. In the late 1980s after filling in many times for guitarist Mike McKenna, Leonard joined as the guitarist for the Kendall Wall Band, providing him the experience of performing with a house band at the Black Swan in Toronto, Ontario.
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