Plenty wrong as shown here:
How can you win if your 4 best players aren't even sniffing the jock of the other team's best players?
If they need so much help they shouldn't have tried to take every last dollar they could get.
In Toronto everything goes wrong:
Rielly is the last greedy/best guy, but he sucks the most (by far)
There were too many passengers, that's true, but we have too many passengers because the top guys collectively are overpaid by like 15+ million dollar
Oh and the top guys obviously don't perform, Nylander is a great example because people think of him as the "good one" from the others, he's definitely better offensively or at least equal, only problem is he is abysmal defensively/lazy and unwilling to get dirty
Management has allowed Shanahan to do this for basically 10 years now, again all parts of the problem (Shanahan's horrendous decisions, management keeping him)
And obviously the goaltending/D have been mediocre to bad to abysmal over the years
All the problems compound and bounce off each other