The narrative seems to be that they're major chokers who regularly lose series they should win. But I think they're more a good regular season team that hasn't had much playoff success but hasn't been upset in the playoffs that often.
Bolded is correct. They are a talented team who's flaws catch up to them in the playoffs. Though starting in the 2018 playoffs, you'd expect them to have more than one playoff series win. 2021 was by far their worst choke. 2020 was the only other one I voted. Yes they underachieved that season, but I still thought they were better than CBJ.
The bigger issue though is no team has been screwed by the current playoff format more than the Leafs, and I'm far from a Leafs apologist. Funny that their two biggest chokes IMO occurred in the pandemic playoff formats. Here's a look at it starting in 2018 looking at who they faced in reality vs who they would've faced with 1-8 seeding, and speculation about how many more playoff series they could've won:
2018: #4 in the East, but had to face #2 Boston in R1. Would've faced the #5 Pens in R1. The Pens were the better team and had the experience, but they were running on fumes from their B2B cup wins. Tough to say how this series goes, but the Leafs at least would've had home ice and not a lot of pressure at this point. Tampa beat NJ in reality (this would've been the 1v8 matchup), and I think Boston beats CBJ (just like the next year) and the Caps beat the Flyers, meaning the Leafs play the Bolts in R2, and I think they lose that series should they beat the Pens in R1.
2019: #5 in the East, but had to play #2 Boston again in R1. Talk about a juicy matchup of the #5 Leafs vs #4 Isles in Tavares' first season in Toronto in 1-8 format. I do think the Isles win this series, as the matchup was favorable to them. In 1v8. CBJ beat TB in reality, same for Boston over Carolina in 2v7 (albeit in the ECF). I think the #3 Caps beat the #6 Pens for the 2nd straight season. So they would've faced the Caps or Pens, and I think they beat either had they upset the Isles, but lose to the Bruins in the ECF just like in R1 in reality.
2022: Returning to the regular playoff format. this was a loaded Eastern Conference, with 6 teams finishing with at least 107 points. The #3 Leafs would face the #6 Bruins, and I feel comfortable picking the Leafs this series. The #1 Panthers beat the #8 Caps in reality, as did the #5 Bolts to the #4 Rangers in the ECF. I also think the #2 Canes beat the #7 Pens. I do think the Canes beat the Leafs, though the Leafs would stand a chance. But they definitely lose to the Bolts in the ECF (they beat the Panthers in reality in R2, and the Leafs in reality in R1). One thing I will say about the real life R1 series they lost to the Bolts as a Bolts fan is the Leafs took us to 7 and were the only team who had to face Brayden Point, our leading goal scorerer from our B2B cup wins. He got injured early in game 7 and missed the rest of the playoffs, yet we beat the Panthers and Rangers by an even wider margin. The version of the Bolts the Leafs took to game 7 might've three peated against the Avs in the SCF had Point been healthy, so it's worth pointing that out about the Leafs when discussing this loss. One could even open up a can of worms of Point still getting injured in R1, and them still getting to the ECF since they beat the Rangers and Panthers without him anyway, but now having to face the Leafs without him instead of with him in reality. The Leafs would definitely have a better shot at winning this series and getting to the finals. But in the finals I think the Avs definitely beat them.
2023: The #4 Leafs face the #5 Rangers, who I think they beat. I also think the #3 Devils beat the #6 Bolts. The #8 Panthers upset the #1 Bruins, and the #2 Canes beat the #7 Isles, just like in reality. I think the Leafs beat the Devils, but lose to the Panthers in the ECF. Basically, the Panthers swap which rounds they beat the Canes and Leafs from reality.
2024: #5 Leafs lose to #4 Bruins, just like in reality.
2025: Still pending, but the #2 Leafs would face the #7 Devils instead of the #6 Sens.
2018 and 2019 are tossups, and I'll split the difference saying they beat the 2018 Pens but lose to the 2019 Isles. 2022 they win in R1, and reach the ECF in 2023. With all this speculation my predicted playoff wins since 2018 in a straight 1-8 playoff format are 4 series wins, 3 more than the single one they have in reality. For those who disagree, this is pure speculation on my part.