The Hockey News predicted back in 2018 that Leafs would win many cups

[Eye of Ra]

Did not turn out so good, did it?

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[K Fleur]

 

[Cup or Bust]

They might win 3 or 4 Cups between the years 3050 and 3060. No one will be mocking the Hockey News then.

 

[BruinLVGA]

To be fair, that cover is only from 6 years ago. More concerning is that they won only 1 playoffs series in 8 tries. That‘s brutal for a team supposed to be a multiple cup winner by now.

 

[Tasteless Beaver]

Other than Fleury standing on his head to single-handedly stop the Jets in the conference final, this one was perilously close to coming true with the 2017-2018 squad. The Leafs never even came close.

 

[tomin]

Blues closed the door on the jets in 19. Good team tho. They were better than any of the recent leafs playoff rosters.

 

[Leaf Fans]

Did not turn out so good, did it?

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They didn’t say when or how many.

 

[SoupNazi]

Wow! No one has ever done this thread before!