Ray Shero and the Pittsburgh Penguins won a lot of games during his tenure including the 2009 Stanley Cup. They also fell short of the dynasty expectations that were placed on the Sidney Crosby and Evgeni Malkin led team.
Like all general managers in the NHL Ray Shero was not immune to making mistakes. Every single person that takes the general manager position is going to make some errors. What separates Ray Shero from mostly every other GM during his tenure with Pittsburgh is that no other GM was gifted two (!) generational superstars the first day on the job.
Despite having this ridiculous cheat code the Penguins have been unable to win a Conference Final game since winning the Stanley Cup in 2009. A lot of that lands on Ray Shero's doorstep.
Ray Shero managed the Pittsburgh Penguins like there were no consequences to a "win now" approach and that futures didn't matter. The reality of the modern NHL is that futures are what keep the machine working. Hockey is a young man's game now and in mostly all cases a player's best years are already gone by the time they hit unrestricted free agency. If you can't trust young players to play and then outsource the work to more expensive, but not as effective veteran players, you are handicapping your own efforts.
This becomes even more damning when you are trading those futures to acquire more costly veterans who are not impact players. A shining example of this strategy was trading two second round picks for Douglas Murray while Simon Despres continued to watch from the press box. I repeat two second round draft picks for one of the worst players in the league when you had playable youth on the cheap watching from above.
To a lesser degree Shero's trade for Jarome Iginla that same trade deadline was another fruitless use of future assets. This time it was a first round pick. Pittsburgh already had Pascal Dupuis and James Neal playing at a high level at right wing in the top six. There really wasn't a fit for another top six right winger. Pittsburgh tried to make Jarome Iginla a left winger (something he still hasn't done anywhere else but PIT) and when that didn't work they played him on the third line over the guy they kept instead of going after Jaromir Jagr. Certainly not ideal.
Even when Shero had draft picks to use they rarely panned out. Shero was unable to draft many impact players or NHL players at all. Don't take my word for it The Pensblog wrote a scathing piece about this very subject which you can find
here
Then there was being loyal to the players that were on the 2009 Stanley Cup winning roster. Being loyal in a hard cap era is not going to do a team any favors (unless you are the Los Angeles Kings and just cheat your way through the ramifications of poor decisions).
This loyalty is what made Shero choose Tyler Kennedy over Jaromir Jagr prior to the 2011-12 season. Jaromir Jagr led teams went on to knock out Pittsburgh the next two consecutive years. The 43 year old Jagr is still a top line player for the Florida Panthers while Tyler Kennedy is back with Shero as a fringe bottom six player.
This loyalty also saw him extend contracts to three aging veterans in the same off-season. Those players were Chris Kunitz, Pascal Dupuis, and Rob Scuderi. These contracts added up to an annual cap hit of 11.0M which is fairly significant. At this point it wasn't so much a refusal to lean on youth but the fact the Penguins didn't have any. Shero forced his own hand into deals like this because he went on consistent shopping sprees with his future assets and drafted poorly with the ones he had. The few futures he did have were young puck moving defensemen who were consistently blocked by aging veteran players.
Shero was fortunate to always have high end skilled players like Crosby, Malkin, and Letang on his roster, but his negligence in providing playable forward depth was one of his biggest shortcomings towards the end of his Pittsburgh tenure. The post-Jordan Staal third and fourth lines were pretty unbearable to watch. All grit and no skill made for one of the worst bottom six groupings in the league.
Courtesy of Tyler Dellow
This isn't to say that Shero never made any good moves for Pittsburgh because he did and it would be unfair to not point those out here as well. His "hockey trades" were usually on point and improved the club. Examples of this were when he acquired Marian Hossa and Pascal Dupuis in 2008. Landing Chris Kunitz for Ryan Whitney worked out very well for the team. A third round pick for Bill Guerin paid dividends. Acquiring James Neal and Matt Niskanen for Alex Goligoski was also a good example of this. Shero even found a general manager to gift him the very useful Jussi Jokinen with salary retained in exchange for peanuts. One of Shero's most unheralded trades was acquiring Tomas Vokoun for a seventh round pick. The always underrated Vokoun saved the 2012-13 Pittsburgh Penguins from floundering out of the first round due to horrendous goaltending and allowed the Penguins an opportunity to make the Eastern Conference Finals.
There were also some good free agency signings. Most notable was Paul Martin, but there were others as well. Players like Ruslan Fedotenko, Petr Sykora, and Steve Sullivan were all cost effective top six free agent signings made by Shero.
However, when you add up everything from Ray Shero's tenure with Pittsburgh you are left feeling underwhelmed. He was gifted a blank canvas with all the best supplies to paint something beautiful and the result looked like somebody who finger painted with high quality paint.
The reality is that Ray Shero's disregard for futures and affection for unskilled grit left the team in a worst spot than when he took it over and it is something the franchise is still trying to fix.
Thanks for reading!
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