The only thing I still strongly disagree with is this notion that Tavares left money on the table to play in Toronto. I mean, did he literally leave money on the table? Sure, considering the Islanders were willing to overpay to keep him from walking for nothing in return. As for the comedy act known as the Sharks -- they were so desperate for talent, after offering Tavares more than McDavid and missing out, they severely overpaid for Erik Karlsson, who was coming off injuries.
Regardless of what the hapless Isles and deranged Sharks were willing to pay for Tavares, the Leafs willingly gave him the second largest cap hit in the league behind McDavid. This was ludicrous for a guy who had a career high of 86 points and never won a thing in the NHL. It was especially ludicrous the following summer when Nikita Kucherov re-upped with Bolts for a 9.5 mil cap hit after winning the Hart and scoring 126 points.
To make matters worse, the Tavares contract set the precedent for the young Leafs. It's virtually impossible to convince your young, in-house talent to take less for the good of the team when you just gave an outsider (not named Crosby or Ovechkin) the second largest cap hit in the NHL. Then you bypass your loyal soldiers who were drafted as Leafs and stitched the "C" on his chest.
I'm convinced that persuading Tavares to "come home" and sign for say 9.5 (like Kucherov did) would have set all the dominos in place to secure team-friendly deals with the pups. If he signs for 9.5 then it's easier to get Willy to agree to a 6.25 deal without practically losing a year. If Matthews wants 11.5, you have ammunition to say, "Come on, we just signed a top UFA for 9.5. If Tavares was willing to sacrifice some coin to be a Leaf, how about you? We can make you the highest paid on the team at 10 mil but let's take a bit less and we'll get you some more players so we can win a Cup together." Then, once Matthews takes 10 or so, there's zero chance Marner holds out for 11 million. He likely settles for a hair below Tavares at 9, which was fair for him.
If you add up those savings, we're talking 6+ million of cap flexibility to surround the core with better depth pieces to make some runs. And what would it really have cost those players? Tavares would still be making Kucherov money and M&M would both be making more than Leon Draisaitl. In fact, Marner would have just about signed for then what Matt Tkachuk just signed for last summer. All of those contracts were outlandish then, and more so now, and they all started with the Tavares deal.