A bad season got worse on Monday night for the Pittsburgh Penguins, when on a delayed call against the Arizona Coyotes, veteran defenseman Kris Letang tried to drop a pass back to legendary center Evgeni Malkin.

Malkin couldn't handle the pass deflecting it into the empty net for an own goal that made it 4-2 Arizona in the third period.

Rarely in sports do we see moments so powerfully symbolic of the sudden end of an iconic era.

With Malkin, Letang, and all-time great Sidney Crosby leading the way, the Penguins won the Stanley Cup in 2009, 2016, and 2017. In every season between 2008 and about now, they've at least been in the picture to compete for it.

This year? Not so much, even as Crosby is turning in an MVP-caliber season at the age of 36.

Pittsburgh Penguins: Where Did it Go Wrong?

Father Time comes for every dynasty or borderline dynasty in pro sports. We just saw it come for the New England Patriots. It came for Michael Jordan. It is coming for LeBron James, and it came for the Penguins.

Despite Crosby's continued brilliance, Malkin and Letang have slipped from being among the very most dominant players in the league to simply being very good players.

That's a normal and expected drop-off, but it's not one that this Penguins franchise was constructed to bear.

New general manager Kyle Dubas took a big swing in the offseason, doubling down on his aging core and adding another older star in defenseman Erik Karlsson to the group.

The gamble paid off, as Karlsson has produced 33 points in 44 games and has been a positive force on the ice, but even that hasn't been enough to stave off the team's decline.

Pittsburgh's problem has been a total lack of offensive production outside of its top six forwards. Crosby, Malkin, Bryan Rust, Jake Guentzel, Rickard Rakell, and Reilly Smith are all averaging half a point per game or higher, but Smith has missed time and both he and Rakell are exactly at half a point per game.

Beyond that, not a single player has produced at anything approaching an impactful level. The Penguins have gotten strong goaltending from Tristan Jarry and Alex Nedeljkovic, but it has not been enough to offset what has at times been an anemic offense.

Where do the Penguins Go from Here?

Last night's loss sent the Penguins down to seventh place in what is a tightly-packed middle of the Metropolitan Division. The Pens are within striking distance of the Capitals, Islanders, and Devils, but they would likely need to beat out all three of those teams and one of the wild card contenders from the Atlantic Division to make the playoffs.

It's not an impossible path, especially with the season Crosby is putting up, but it is a very unlikely one.

This puts Dubas in the unenviable position of having to be the one to decide to pull the plug on this storied era of Penguins hockey in just his first year on the job. It's complicated by the fact that he was brought in to do his best to extend it.

The Penguins could opt to sell at the deadline and begin what could be a long and arduous process of collecting assets to build a new young core

The problem is Pittsburgh sent this year's first-rounder away, albeit with top 10 protections, to San Jose to acquire Karlsson, and they don't have much in the way of quality players on expiring deals.

They do have a star winger in Guentzel, and the 29-year-old would be sure to command a bounty of assets if the Penguins make him available.

Trading Guentzel would be a clear statement to the fan base that this era is over. The question for Dubas is whether or not making the right decision is worth the potential alienation of not only his fans, but the veteran trio of Crosby, Malkin, and Letang, all of whom are signed beyond this season and expect to compete.

Could any of them be traded? The notion of Crosby in another uniform is virtually unthinkable, but that's not really the case with Malkin.

Whatever the decision winds up being, it's time to cope with the reality that this trio likely will not lift another Cup together as Penguins.

Whether it's best for the franchise for them all to play out the string together in the Steel City to preserve their one-team legacies or move on, one disastrous play in Tempe laid the reality bare.