Made his career in Canada just refers to he kept his home in Toronto while making in big world wide.
There was a time when it was viewed to make it, you have to move to New York, Nashville, L.A etc. There was a view that you could never make in the music business by staying in Canada. Paul Anka who is from Ottawa where I lived thought and perhaps did have to move to New York to make it. There are lots of other examples.
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