I made a table in order to rank teams based on their history and number retirements.
The history takes account two things - the years contested and the number of Stanley Cups won. For each team I counted only their history in their current home as teams tend to evaluate their history differently - Stars respect two number retirements made by North Stars while Hurricanes and Avalanche have taken retired numbers from the previous home back to circulation. So I have counted Stars have 24-year-history and not 50. With Lehtinen's number going to rafters early next year, they have then three - Broten and Modano numbers have officially retired by Dallas Stars even though both played for North Stars (and in Broten's case, most of the career was in Minnesota)
One Stanley Cup adds 10% to the years contested. Therefore comparing two of the 1967 expansion teams, Blues with no Cups stands at 50, Penguins with 5 Cups is at 75. The Original Six takes first six places, with Canadiens on top at 367,2 (pre-NHL years counted, so it's 108 years * 3,4 thanks to 24 Cups)
This number is then divided by numbers retired +1. This +1 added so that teams with no retired numbers can be compared. Of those teams, Sharks have most years in business with 26.
Note that if number is retired for two players (such as Canadiens #16 for Elmer Lach and Henri Richard) it is only counted once.
SJ | 26 | | 26 | | 26,00 |
PIT | 50 | 5 | 75 | 2 | 25,00 |
DET | 91 | 11 | 191,1 | 7 | 23,89 |
MTL | 108 | 24 | 367,2 | 15 | 22,95 |
CHI | 91 | 6 | 145,6 | 6 | 20,80 |
NSH | 19 | | 19 | | 19,00 |
CBJ | 17 | | 17 | | 17,00 |
TOR | 100 | 13 | 230 | 13 | 16,43 |
NYR | 91 | 4 | 127,4 | 8 | 14,16 |
CGY | 37 | 1 | 40,7 | 2 | 13,57 |
BOS | 93 | 6 | 148,8 | 10 | 13,53 |
ANA | 24 | 1 | 26,4 | 1 | 13,20 |
FLA | 24 | | 24 | 1 | 12,00 |
VAN | 47 | | 47 | 4 | 9,40 |
TB | 25 | 1 | 27,5 | 2 | 9,17 |
NYI | 45 | 4 | 63 | 6 | 9,00 |
WSH | 43 | | 43 | 4 | 8,60 |
LA | 50 | 2 | 60 | 6 | 8,57 |
PHI | 50 | 2 | 60 | 6 | 8,57 |
MIN | 17 | | 17 | 1 | 8,50 |
EDM | 45 | 5 | 67,5 | 7 | 8,44 |
OTT | 25 | | 25 | 2 | 8,33 |
NJ | 35 | 3 | 45,5 | 5 | 7,58 |
DAL | 24 | 1 | 26,4 | 3 | 6,60 |
STL | 50 | | 50 | 7 | 6,25 |
WPG | 6 | | 6 | | 6,00 |
BUF | 47 | | 47 | 7 | 5,88 |
CAR | 20 | 1 | 22 | 3 | 5,50 |
ARI | 21 | | 21 | 3 | 5,25 |
COL | 22 | 2 | 26,4 | 6 | 3,77 |
VGK | 0 | | 0 | | 0,00 |
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Coyotes was a bit of difficult to evaluate - officially they have honored but however no played has used 7, 27 or 97 since the honoring ceremonies I included them. The table also has non-player numbers (MIN #1 and FLA #93) included.