Are those the guys that play in Make Believe Garden? 
For what it’s worth, I always thought that it referred to the Canadian flag, which bears a single maple leaf. But that doesn’t make sense since the Leafs exist since 1926 (renamed from the “St. Pats”), and the flag was adopted in 1964. Still, the former flag (the “Red Ensign”) contained the coat of arms which bore three maple “leafs”. The song “Maple Leaf Forever”, composed in 1867, the year of confederation, was an unofficial national anthem in English Canada. The Maple Leaf had been a Canadian symbol for a long time.
So, when Conn Smythe renamed the St. Pats in 1926, he was thinking of the Maple Leaf, the symbol, not the things that hang from trees and are scattered on the ground in November, aka maple leaves.
Check Wikipedia for cite, articles on the Toronto Maple Leafs, the Maple Leaf, and the Canadian Flag.
Maple Syrup is the bollox. 
Note that while Cheez Whiz, according to the spelling indications, does not contain actual cheese, it does apparently contain real whiz.
What I want to know is, why are the Boston Celtics called the SELtics, huh? That’s just wrong.
Don’t you roll your eyes at me! As the previous discussion has indicated, this is a real linguistic question, not just some random decision by team owners. You imply this decision is completely arbitrary. It’s a legitimate question to ask why Toronto made a different choice on the pluralization than Minnesota did. Of course they don’t have to follow the same rules, but why do they follow different ones?
To my ear, “Maple Leafs” is in fact a much more natural construction than “Timberwolfs,” when referring to team members. suryani provides some reasons why this might be so. “Maple Leaf” is well removed from its original meaning - an inanimate and symbolic object - so it makes sense that when applied to a player it might use a regular plural. In contrast, a player might actually be seen to be the personification of a Timber Wolf, an animate being, so that this name is less removed from its original meaning and hence retains the irregular plural.
“Curt Schilling is now a Boston Red Sock” is no better. What’s wrong with “He is now with the Red Sox” or “He now plays for the Red Sox” or “He has joined the Red Sox.”
Nonsense. The Associated Press Stylebook, for example, directs you to remove all commas before “Inc.” and “Jr.,” regardless of the preference of the entities or individuals involved. It also says that acronyms that are pronounced as words rather than as a series of letters, such as “Alcoa,” “Pepco,” and “Geico,” are to be written with an initial capital letter only, not as “ALCOA,” “PEPCO,” and “GEICO,” regardless of the company’s preference.
My viewpoint is that capitalization is a grammar issue, not a spelling issue. My own personal style is to capitalize all personal names with one capital letter at the beginning, ignoring all weirdo capitalizations invented by marketers – so for me it’s “Ebay” and “Compuserve,” not “eBay” and “CompuServe.”
“I ask him who own de Chiefs”
“What he say?”
“OWNS, OWNS”
Well, sure, there are ways around it (you can usually just say “Red Sox player” or "member of the Red Sox), but these just avoid the issue. There really isn’t a good singularization for “Red Sox/White Sox” in reference a player.
I guess this also explains why, when an NHL player moves to St. Louis, he is now said to be a “Blue”.
Is that good or bad?
Nothing to add to the discussion, except to mention that my keyboard and monitor are now covered in Diet Pepsi.
And I have shared Jenaroph’s observation with a few friends. 
Thanks for the laugh!!!
You could go on and on.
Take a team called “The Tide”. A player is Tide? A member of…
The Jazz…the Wave…whatever. It doesn’t have to make sense.
A single leaf is a symbol, but the collection of leaves is meaningless as it pertains to Canada. Ergo…the Maple Leaf…the collection being the Maple Leafs.
There’s a strong natural tendency to pluralize even singular team names, in a battle against abominations - for instance, the New England Revolution are much better known as the Revs.
I thought the underachieving Tronna team was the Make Beleafs, though.