Okay so, the longer this conversation went on, and the longer people didn't address the OP's question, the more I became interested to know the answer. So I did a little digging into some numbers.
Full disclosure: I'm a Pens fan.
That said, I also have no animosity towards, nor disrespect for the Hawks and what they've accomplished, and would be THRILLED if the Pens were able to replicate the Hawks 3-in-6 feat. I have the utmost respect for them, and felt I could offer a fairly objective answer to OPs question. There's already a discussion in the Playoffs board about the Pens (and Hawks) and what constitutes a dynasty, which team is closer to being a dynasty, and I support the idea of the Hawks as having been closer to a dynasty than the Pens.
First of all, let me reiterate that the OP defined the timeframe we're speaking about as 2005-2006 to 2017-2018. That's a 13 year span, and that's how I'm measuring this.
The first thing I wanted to do is actually define "Success" in the context of "Franchise". I think there's a number of ways you can define "success" (as a fan) and also as a "franchise operator". It's unclear if the OP intended for financials to play into the answer, but when I hear "Franchise" used in the context of success, my mind tends to include the "Business" component, as opposed to when I hear "Team" I just think of straight up on-ice performance. That's fine if you don't see it that way, but I pulled some numbers incase there are others who are curious, and/or see it the same way.
In my mind, and I'm sure you all agree... on-ice Success starts and ends with Cups. From there I tend to look at Playoff Runs, and then Regulation Records.
As far as the Business side of it goes (and I'm sure someone from the Business of Hockey board could really elaborate and expound on this stuff), I see two measures of success. 1) Franchise value & subsequently 2) Fan participation. One begets the other to certain extent.
Also, please keep in mind I went into this research exercise knowing very little about the Blackhawks, statistically and financially, so I wasn't cherry-picking these categories to measure success to suit any kind of narrative. I was genuinely curious as to how the numbers fleshed out.
1) Stanley Cups
Both teams have 3 cups in 13 years. I don't care whether they were all consecutive, or smattered across the timeframe given... 3 cups is 3 cups... Period. I think some people would give the nod to the Penguins for their 2008 SCF appearance, as a tie-breaker of sorts, but I'm not going to do that here.
(Valuing cups in terms of QoC or depth of field is an interesting thing that I might explore the math of privately for kicks. Edit: Done
http://hfboards.mandatory.com/threads/cup-success-measured-against-field-size.2489849/)
Summary: Tie
2) Playoff Runs
I'm not suggesting this method is the de-facto way measuring a team's success, it's simply a method I thought was fair (from my perspective as a fan), in terms of being a simplistic way of resolving a team's playoff success mathematically. I'm totally prepared to defend my rationale for this system, and I'm also totally open to hearing alternate solutions and alternate proposed systems.
I awarded the teams points based on the following criteria for each year:
0 = Did not qualify for playoffs
1 = 1st round appearance
2 = 2nd round appearance
3 = 3rd round appearance
4 = 4th round appearance
This is how it played out:
Pittsburgh Penguins
0,1,4,4,2,1,1,3,2,1,4,4,2
29pts
Chicago Blackhawks
0,0,0,3,4,1,1,4,3,4,1,1,0
22pts
Summary: Pittsburgh Penguins have had more Playoff Success outside of Stanley Cups
3) Regulation Records
This is dead-easy to measure, and needs very little prefacing.
Pittsburgh Penguins
1032GP - 583W - 342L - 107OTL
Chicago Blackhawks
1032GP - 544W - 364L - 124OTL
Summary: Pittsburgh Penguins have seen more On-Ice Success in terms of Wins and Losses, during the Regular Season, which is where the bulk of the games the two teams have played in the given timeframe is.
4) Franchise Value
If we want to know which franchise has seen the greatest financial and brand gains in a given timeframe, we need to look at their growth in that timeframe. I thought the Forbes valuation would be a decent metric for that, and without already knowing what the numbers would be, this is what I found:
Forbes Value
Pittsburgh Penguins, $264 Million, 161.4% growth from 2005-2018 (#1 NHL)
Chicago Blackhawks, $306 Million, 71.9% growth from 2005-2018 (#9 NHL)
Source:
NHL Franchise Values Before and After the 2004-2005 Lockout
Summary: Pittsburgh Penguins have been more successful as a business, from a growth perspective, in the given timeframe.
5) Fan Participation
Fan Participation is critical to a hockey org's success. This one's tricky however, because obviously the markets are completely different, in terms of economics and size. I opted to examine Fan Attendance* based on Arena Capacity as a way of looking at which team was the most successful in terms of drawing people to the gates and to the games. This is what I came up with:
Pittsburgh Penguins
16,940 x (205g) (2005-2006) + 18,387 x (304g) (2010-2011)
3,417,715/3,472,700 Mellon Arena
5,797,696/5,589,648 PPG Paints Arena
--------------------
9,215,411/9,062,348
101.7% Capacity
Chicago Blackhawks
19,717 x (509g)
10,324,799/10,035,953 United Center
102.9% Capacity
Attendance Souces:
Pittsburgh Penguins home attendance 2005-2018 | Statistic
Chicago Blackhawks home attendance 2005-2018 | Statistic
*I assumed all teams played half of their schedule at home, and I did not account for any home games over-seas (Sweden, London, etc)... for the sake of simplicity.
Summary: Chicago Blackhawks have seen more success at the box office, in terms of their ability to draw more people to their games, in the context of raw numbers as well as arena capacity.
In conclusion, I'd look at those 5 things and lean towards crediting the Penguins as having been the greater franchise in the last 13 seasons. I'd be happy to hear any other factors you guys think should be accounted for that you feel I've overlooked there. Apologies for any grammatical or mathematical errors, please let me know if you spot any, and I'll fix them up right away.
