The long and short of it is "would every fanbase trade places with us over the last 10+ years?" Now that Chicago is firmly in the crapper, the answer is "YES" across the entire league. Like they said, f*** the haters. For all our griping, we have it better than anyone. The Pens are now the co-most successful expansion franchise in the league. As many or more cups than every other non-O6 team. More cups than the Rangers, who have been around for like a thousand years. And all or most of the success has happened within our lifetimes.
As far as the details, is anyone really talking about "failing to stop" Ovechkin? He got a single victory over us. One, in 13 years. This could've been known as the Ovechkin-era of the league, except for the fact that Sid, Geno, and (supposedly inferior) Pens teams repeatedly threw him and the best Caps squads ever into the dumpster. Often in the most brutal, soul-crushing possible ways. The only people who I assume care about "not stopping OV" are Flyers fans, who are pissed off Washington also won a cup because their own team has won the square root of zero.
Another note, Chicago didnt really win more. They won them in six years (rather than eight) but their franchise is now a dumpster fire and they wont be winning anything else. That's more than offset by the back to back, IMO. By a whole lot. First franchise since the "Red Machine" Wings to win back to backs. Back to backs were rare enough in the 90s NHL, and they only happened for absolutely loaded teams. I assumed they would be nearly impossible in the cap-era league.