06-07 - 1st round exit to Ottawa - learning on the job
07-08 - Finals loss to Detroit - 4-2 series against much more experienced team
08-09 - Cup #1
09-10 - 2nd round exit to Montreal - Blackhawks would win the Cup - below expectations
10-11 - 1st round exit to Tampa - everyone hurt - No chance, next
11-12 - 1st round exit to Philly - Kings would win the Cup - definitely below expectations
12-13 - 3rd round exit to Boston - Blackhawks would win Cup - would've been the big Pens/Hawks in their prime final..
13-14 - 2nd round exit to NYR - Kings win Cup - organizational restructure
14-15 - 1st round exit to NYR - Blackhawks win Cup - no chance to compete in this one unlike '10 and '13
15-16 - Cup #2
16-17 - Cup #3 - first back-to-back with Salary Cap
17-18 - 2nd round exit to Caps - Caps would win the Cup - fair play, won 9 straight series'
18-19 - 1st round exit to NYI - Blues win Cup - definitely below expectations
19-20 - MTL - no comment
So Since Sid (first year without Malkin) - 3 cup wins, 4 Finals.
No missed playoffs
In my opinion, 5 "bad" exits - either too early for the talent they had or way below expectations
Not bad