Year after year, each team in the NHL grapples with the question of where they stand in terms of contending for the Stanley Cup. Teams like the Buffalo Sabres are stuck in a floundering state in the league’s basement, while the Tampa Bay Lightning have a seemingly unbeatable squad.

The Pittsburgh Penguins have had their own issues with where they stand on this meter for the past few seasons. A team that features Sidney Crosby and Evgeni Malkin will always be in the Cup conversation, but those two won’t be around forever. In fact, and this may feel frightening to hockey fans, we’re closer to the end of their careers than the beginning.


Win-Now Mode

Following the Penguins’ second Cup win in as many years in 2017, then-general manager Jim Rutherford vowed major changes to the team. While 2017-18 was a turning point year for the team, it marked the beginning of a strange era for the Penguins. The era of being in “win-now mode.”

The definition of “win-now mode” is simple enough. Do whatever it takes to bring future Hall of Famers Crosby and Malkin one last Cup. The two aren’t getting any younger and it’s only a matter of time before their play starts to take a decline. “Win-now mode” also goes hand-in-hand with the questions around the Penguins’ “Cup window.” Is it still open? Can Crosby and Malkin still cut it in the postseason? Is the window already closed?

Bringing in young, bright players like Teddy Blueger and Kasperi Kapanen is a great way to help extend the Cup window and have a good grip on win-now mode. But there have been many missteps along the way and most of them only have one man to blame: Rutherford.


Rutherford’s Decision Making

While Rutherford’s intentions were in the right place with some of his moves, they did nothing to help the team and did a lot to compromise the future. You don’t have to look too much further than the contracts he signed off on following the 2018 Playoffs.



On July 1, 2018, the Penguins signed 31-year-old defenseman Jack Johnson to a five-year, $16.25 million contract. This signing was immediately viewed as an awful contract by the fan base. Johnson wasn’t the same player he was after being picked third overall in the 2005 NHL Entry Draft. He wasn’t going to score 40 points and was a career minus-109 at that point.

Only two logical explanations can be seen as to why the Penguins signed Johnson. He and Crosby went to Shattuck St. Marie’s together and became close friends, and Rutherford was the general manager of the Carolina Hurricanes who drafted Johnson in 2005. So, he’s a former Rutherford draft pick who has a Crosby connection.