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Where did Ray Shero go wrong?

2013 NHL Stanley Cup Final - Game Four

Ray Shero

NHLI via Getty Images

When Ray Shero took over as the Pittsburgh Penguins general manager in 2006, he had a golden opportunity. Sidney Crosby and Evgeni Malkin had been drafted in the previous two years, giving the team the foundation for a dynasty.

In 2008, Crosby and Malkin led Pittsburgh to the Stanley Cup Final. One year later, the Penguins won it all. They haven’t done it since, and Shero has been shown the door as a result.

What could Shero have done differently? Certainly, he made some good moves along the way. In recent years he traded for forwards James Neal, Chris Kunitz, and Pascal Dupuis, and signed them all to reasonable contracts. Each member of that trio has grown since joining the Penguins, giving them a formidable group of top-six forwards.

But what about their bottom two lines? Championship teams are known for their depth and that’s hard to get when you have $17.4 million annually ($18.2 million starting in 2014-15) of your cap hit going to two forwards, no matter how talented they might be.

That’s a problem the Chicago Blackhawks haven’t had to deal with. Yet. Like Pittsburgh, Chicago is built around two young superstars in Jonathan Toews and Patrick Kane, but that duo is costing the team just $12.6 million annually against the cap. Both are pending unrestricted free agents after the 2014-15 campaign, however.

What could Shero have done to prevent this problem? The bold move would have been to trade one of Malkin or Crosby -- likely the former rather than latter. He could have practically dictated the price and built the offense around Crosby, while retaining enough cap flexibility to assemble a balanced group.

Or, he could’ve just drafted better. Since the 2008 draft, the Penguins haven’t selected a single player that has gone on to participate in at least 100 NHL games.

Using Chicago as a comparison again, the ‘Hawks have drafted three forwards since 2008 that have surpassed the 100-game mark: Andrew Shaw, Brandon Saad, and Marcus Kruger. Ben Smith is just shy with 95 regular-season contests -- which is still more than any Penguins drafted player (Simon Despres, 85) has managed over that span.

All four of those Blackhawks were taken after the first round. Since 2008, the Penguins have just one non-first round pick that has played in at least 15 NHL games: Ben Hanowski, who’s no longer with the organization.

Then of course there’s the Penguins defense. It’s rare for any team to win the Cup without a superb blue line, and while Pittsburgh does have Kris Letang, its defense as a whole is somewhat less than superb.

Shero tried to address that by bringing in defensive defensemen, but his recent experiments -- veterans Douglas Murray and then Rob Scuderi -- haven’t produced the results he was hoping for. Ultimately, in both cases it might have been a matter of chasing after players that were past their primes.

The next Penguins general manager will have to decide if he wants to stay the course or do something bold. The depth problems in Pittsburgh aren’t going to get any easier to address given that Letang’s eight-year, $58 million contract is about to begin. Can this team stay competitive while giving more than $25 million annually to just three players?

Shero clearly thought they could. The next guy might disagree.

Related: Now is the time to explore trading Letang

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