Been reading into this concept of "leader's courtesy." In 2002, then-leader of the Canadian Alliance, Stephen Harper, won a by-election in which the LPC & PCs did not field a candidate. As I understand it, usually the gov't of the day that extends the courtesy. Not oppo parties.
As in many cases, this riding was already held by his party (technically held by the Reform Party). In his case, he was taking over from Preston Manning. Just as Stockwell Day took over Jim Hart's seat in a 2000 by-election.
In the case of Stockwell Day's by-election, the Liberals also did not run a candidate against him. Again, they were the government at the time they extended this courtesy.
Going back a bit further, to 1990, Liberal MP Fernand Robichaud stepped aside so his newly-elected leader Jean Chrétien could (re)enter Parliament through a by-election. Again, the government of the day (Brian Mulroney's PCs) did not run a candidate against him.
Interestingly, when the Liberals were in power in 1983, they did not extend this courtesy to new PC leader Brian Mulroney. He entered Parliament via a by-election that Elmer MacKay stood aside for (again, an MP from the same party).
Tommy Douglas twice entered through a by-election. 1962, when Erhart Regier stepped aside for the new leader; 1969 after the death of colleague Colin Cameron (Douglas narrowly lost re-election in '68 in his newly drawn riding). The Liberals didn't extend the courtesy either time.
In 1948 (now we're really going back), G. Russell Boucher resigned to let his newly-elected PC leader, George A. Drew, enter Parliament. The Liberal government at the time did extend the courtesy of not fielding a candidate.
I could go on because there are some other fun cases further back, but this thread is getting long. So I am going to summarize what I've found and my thoughts on this. Here is generally what I am seeing so far with regards to the history of the "leader's courtesy":
1. It's not consistently used; hence it's a courtesy, not a rule

2. Until 2019, it was expected that the gov't of the day was supposed to extend the courtesy to the opposition part. Not a fellow opposition party.
3. In a few cases, a PM ran to get into Parliament. For example, William Lyon Mackenzie King in a 1945 by-election. Courtesy was extended to him by all parties.

4. In at least one case, a leader ran with the courtesy and lost to a fellow oppo party: Arthur Meighen in 1942.
My thoughts are complicated.

It's fair to argue that it's anti-democratic to not allow constituents a full say on who they elect if not all parties are running. I also believe there's merit to the idea that every party with a seat & whose leader is seatless is losing a key voice
Some parliamentary & political traditions, interesting as they can be, maybe don't serve a 21st-century democracy well anymore. I think this may be one of them, and not because I don't believe in cooperation. It doesn't address the systemic issue of our outdated electoral system.
I would have to look to other countries to get a better comparison, but I would suggest that our electoral system is the real issue here.

But where does that leave the situation of newly elected Green leader Annamie Paul?
It is unlikely that the current gov't is going to work with Parliament to make electoral reform (specifically proportional rep) happen soon, certainly not before the by-election, that leaves one option in the interim: if courtesy is extended by anyone, it should be the Liberals.
This would be in-line with the general "tradition" of the "leader's courtesy," which is for the gov't of the day to not run a candidate against a leader trying to enter Parliament via by-election.

Otherwise, Annamie Paul will have to fight this by-election as she did in 2019.
For what it's worth, I do believe the leader of the Greens has earned a voice in Parliament. She represents a party with seats & that received over 1.1M votes. In a better electoral system, she wouldn't need to worry about some inconsistent courtesy or running in a strategic seat
But what do I know, I'm just a political science student. Perhaps, as Éric Grenier says, it would make more sense for one of the 3 current Green MPs (probably May) to step aside. Odd note to end on, but this concludes my thread. https://twitter.com/EricGrenierCBC/status/1313153170114326529
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