Leonard began his musical career at the age of five, playing the drums in church. At that time his father played the steel guitar. As Leonard grew older his interest in the instrument developed until the age of nine when he began to play the steel guitar regularly in church. As he grew with the instrument he quickly gained notoriety around the city for being the youngest and one of the most talented steel players around. Today at 23, he can be seen at various venues in the Syracuse area as well as with the Custom Taylor Band.