Susan Crawford wrote on and talked about this (mis)handling of telecoms in the US context years ago, the government letting the companies divide regions up and ensure a lack of competition.

My reading of the situation in Canada for internet and wireless is that it was a historical mix of:

• lacking political will/interest to govern from day one
• a policy of letting the free market run until it’s a major problem
• follow the US lead for anything new
• and support the (then) recently de-regulated incumbent (Bell) to dominate
• give competitive advantages to Canadian companies vs allowing foreign competition even if it means worse outcomes for Canadian consumers (better to protect the Canadian economy from foreign interests than to ensure consumer best interests).