I thought it would be fun to measure the "value" of a Stanley Cup, year-by-year, as determined by the number of teams competing for it. This idea came about when I was thinking about how the 1950s Habs 5-straight Cups weren't as impressive to me as say; the Hawks 3-in-6. The reason is that I don't personally find it "impressive" that 1 team wins a cup in a small field of 6 teams. I might be underestimating the difficulty in that, but it's moot, really.

So with that in mind, I set about weighting each Stanley Cup. I'm somewhat confident I didn't make any mathematical errors, but I certainly didn't go back through and double-check all of my work.

I started with the 1914-1915 season as it was the first season an NHL team could compete for the SC. Even though those early SCs were NHL champions battling against PCHA champions (or other leagues when applicable) for the Cup, I considered the total numbers of teams eligible to compete for the cup as part of a "greater unspoken league" of teams, and therefore the combined number of teams present in all the leagues, relevant.

I assigned each Stanley Cup a value in points as determined by the number of teams in the "league". Such that, 6 teams competing for the cup, gives the value of the cup that year "6 points". If a team won a cup in a year when the league had 12 teams, the cup was worth 12 points that year.

Here is the spreadsheet, for anybody that wants to view it, it's nothing special.
Winners listed in lowercase are long-defunct teams that I didn't care to track. Year is listed as the year culminating in the Cup victory. For example the 1956 Cup-winning Canadiens are the 1955-1956 Canadiens.

From there, I set about tallying the points for each Cup winner:
MON - 9,8,10,10,6,6,6,6,6,6,6,6,6,6,12,12,14,16,18,18,18,17,21,24 = 267
TOR - 7,7,8,7,6,6,6,6,6,6,6,6,6 = 83
DET - 8,8,6,6,6,6,6,26,26,30,30 = 158
BOS - 10,7,7,12,14,30 = 80
CHI - 9,8,6,30,30,30 = 123
EDM - 21,21,21,21,21 = 105
PIT - 21,22,30,30,30 = 133
NYR - 10,9,7,26 = 52
NYI - 21,21,21,21 = 84
NJD - 26,28,30 = 84
PHI - 16,16 = 32
LAK - 30,30 = 60
COL - 26,30 = 56
DAL - 27 = 27
CAL - 21 = 21
ANA - 30 = 30
CAR - 30 = 30
TBL - 30 = 30

And then I determined the number of points available to teams based on their founding date, or first NHL season where they were eligible to compete for the cup.

MON - 1914 = 1531 pts
TOR - 1917 = 1503 pts
BOS - 1924 = 1460 pts
CHI - 1926 = 1435 pts
DET - 1926 = 1435 pts
NYR - 1926 = 1435 pts
DAL - 1967 = 1148 pts
LAK - 1967 = 1148 pts
PIT - 1967 = 1148 pts
PHI - 1967 = 1148 pts
NYI - 1972 = 1084 pts
COL - 1972 = 1084 pts
CAL - 1972 = 1084 pts
NJD - 1974 = 1052 pts
CAR - 1979 = 963 pts
EDM - 1979 = 963 pts
TBL - 1992 = 689 pts
ANA - 1993 = 665 pts

I then applied the number of points earned against the number of points available to determine each team's success quotient, and then ranked them based on the results.

MON - 267 / 1531 = 0.1743
PIT - 133 / 1148 = 0.1158
DET - 158 / 1435 = 0.1101
EDM - 105 / 963 = 0.1090
CHI - 123 / 1435 = 0.0857
NJD - 84 / 1052 = 0.0798
NYI - 84 / 1084 = 0.0774
TOR - 83 / 1503 = 0.0552
BOS - 80 / 1460 = 0.0547
LAK - 60 / 1148 = 0.0522
COL - 56 / 1084 = 0.0516
ANA - 30 / 665 = 0.0451
TBL - 30 / 689 = 0.0435
NYR - 52 / 1435 = 0.0362
CAR - 30 / 963 = 0.0311
PHI - 32 / 1148 = 0.0278
DAL - 27 / 1148 = 0.0235
CAL - 21 / 1084 = 0.0193

I think this confirms what we all pretty much knew: The Montreal Canadiens are the Stanley Cuppiest Team of All-Time. But, it's neat to see how all the other teams fare, and to see how their Cup Success can be viewed in this light.

I hope you all can read this. I really don't want to have to format it.

***Updated to omit 1919, 2005, and 2018 Cup Values in teams' Points Available (since the Cup couldn't be won in 1919 & 2005, and 2018 hasn't completed yet).