The total points standings can be found below, but it is probably no surprise, that the Detroit Red Wings are tops on this list. The Wings make the playoffs every season and won the Stanley Cup in 2008. Every organization pines to have the Wings’ consistent contending squads.
Second on the list are the San Jose Sharks and Pittsburgh Penguins. These teams are interesting in their differences. The Penguins tanked a little before the lockout and were ready to go with Crosby and company post-lockout. Two Stanley Cup appearances, including a Cup victory in 2009 have made the Penguins a model organization. Conversely, the Sharks have been consistently a playoff team with the talent to make a run at the Cup. The Sharks have never made it past the conference finals and haven’t been really close to winning in any of those conference finals to begin with.
We attempted to do something similar thing a while back, but this recent piece handles the topic much better and looks at the entire league. It's worth a read when you get the chance.
Every team struggles at some point. Does that mean that the struggles are acceptable? Sometimes yes and sometimes no.
It's impossible for a team to win every year. Obviously, it would be great if the Pens were battling for the Cup each season, but that's simply not realistic for any team in any sport. There will be years that end in disappointment, no matter who is on the team, who is running the team or who the competition is. No one could have realistically predicted a New Jersey/Los Angeles final in 2012. This shows the unpredictable nature of the NHL. Many, many teams were thought to have better shots at the 2012 Cup than both of those teams and yet they all failed. So is failure "okay" sometimes? Maybe it depends on the kind of failure. We're not sure.
Pollock asks a similar question:
As a fan, would you prefer a top rated playoff team year-by-year or the off-and-on success of the Carolina Hurricanes (eight points since the lockout)? Each fan probably has a different opinion but it is those types of debates that sports are all about.
Failing to accomplish a goal is always tough and when you fail to reach a goal you should certainly take as many steps as possible to improve in the future and avoid a similar fate the next time. However, even if you do everything "right." you can still end up watching while other teams move on. That's just sports.