In the outset, he performed with a local band called Soul Sausage then later became the sideman for Juno Award winner, Morgan Davis.

King, Robbie Robertson, Garth Hudson and Rick Danko of The Band and played a tour with blues musician Colin Linden.

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.

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, Morgan Davis, Johnny V Mills and Cash McCall.

[10] In 2001, Leonard joined and has remained a member of The Maple Blues Revue, which was formed by Gary Kendall and Pat Carey.

[11][12] In 2003 he received with the Fathead band the Canadian Indie Award, for Blues Recording of the Year for their song, First Class Riff-Raff.

Leonard also serves as lead guitarist for Erin McCallum, and remains in high demand as a freelance player.