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Where did Ray Shero go wrong?

May 16, 2014, 1:16 PM EDT

Ray Shero 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

  1. sprtsfan1 - May 16, 2014 at 1:20 PM

    Wrong guy got fired

    • kaptaanamerica - May 16, 2014 at 5:37 PM

      Shero needed to go for not making the right moves to build a winner despite having Crosby and Malkin. Crosby needs to be traded since everyone knows he can’t lead this team to the cup.When they won it was Malkin doing the heavy lifting.

      Malkin needs to be the centrepiece of the organization and the team should be built around him.

      • lallin66fan - May 16, 2014 at 5:50 PM

        Trade the best player in the Nhl would be the most stupid thing ever. Shows you know nothing anout hockey or you just hoping to get Sid on your team…

      • mshantz22 - May 16, 2014 at 6:28 PM

        Where were you in 2009? Crosby lead his team to back to back finals and wins cup the second time. Now, I absolutely loathe Crosby. I think he’s a fabulous offensive player, but he never mans up when he cheap shots people and always is made to look like the victim. That being said, trading him would be a fabulous idea…if you wanted to completely dismantle the franchise. Fire Bylsma, get a goalie not named Marc-Andre Fleury and pick up a second pair defensive defenseman.

      • kaptaanamerica - May 16, 2014 at 9:23 PM

        I’d like to see Crosby playing in Florida or Phoenix.

    • imleftcoast - May 16, 2014 at 6:25 PM

      If he had traded with Vancouver for Kesler at the deadline (a very doable deal), Pens would still be in the hunt, and Shero would have kept his job (most likely, although Gillis would still be fired).

  2. steelhammer92 - May 16, 2014 at 1:24 PM

    You forgot to include the #1 thing he did wrong.. He kept Bylsma too long.

  3. bcsteele - May 16, 2014 at 1:25 PM

    I still think they should trade Malkin. They could get a ransom along with beefing up their overall depth.

    Just saying though…still don’t think it’ll happen.

    • apkyletexas - May 16, 2014 at 2:35 PM

      If you trade, trade Letang. He’s really an offensive threat dressed up like a defender, and you could get a nice haul and a good amount of cap room for him.

      Based on results the past three years, if you had to trade one of Malkin or Crosby, you might have to keep Malkin and let Crosby go. Especially with his injuries and concussions that messed up 3 of those 5 years. A bruising team with speed and power and grit built around Malkin could still compete for a cup. I don’t think that Sid by himself is leading a team anywhere.

      • pdmjr - May 16, 2014 at 3:59 PM

        Malkin won’t approve a trade

    • nyrnashty - May 16, 2014 at 2:44 PM

      I’m not so sure they could get a crazy return for Malkin because every other team knows he’s gettin paid 9.5 million dollars and Pitt is desperate to remove big cap if they were to trade him. He’s a great player, but 9.5 is too much for one guy. Who would add them to their roster, would you want a 9.5 million dollar player? You’ll end up like Pitt unless you draft amazing players. The cap will show a GM’s weakness and at this point of time, most GM’s still don’t seem to understand spreading the money around their roster and the importance of drafting. You have to be willing to flip guys, not sign them to lifetime contracts. Most of these GM’s are still thinking pre 05-06.

      • apkyletexas - May 16, 2014 at 5:41 PM

        If you made it known you were trading one of the top 3 or 4 skilled players in the league, a guy who is a beast on the ice – I think several teams would gladly line up to pay him $9.5 million per year. Malkin could change a team’s fortunes overnight.

    • kaptaanamerica - May 16, 2014 at 9:26 PM

      You can’t trade your best player when their are other options, like trading Crosby.

  4. bobhpine - May 16, 2014 at 1:26 PM

    Horrible drafting, crippling signings (Letang, Scuderi), splashy trades that didn’t work (Morrow, Iginla, Murray, Ponikarovsky, Kovalev—although Hossa, Dupuis and Jokinen were great trades–not sure if having James Neal on this team ever did any good, the guy is a punk, Niskanen is a nice player, but one they already have like 6 of), sticking with Bylsma after getting embarrassed by Philly and Boston, sticking with Fleury who didn’t return to clutch form (he just didn’t, he was only ok) and acquiring zero toughness.

    Other than that, it was stellar.

    This team is so bereft of minor league forward talent it’s scary. Pouliot, Doumolin and Harrington might be good D, they might not. But there is not one forward that will play in the NHL in their system…and Kunitz is 34, and Dupuis is 35, and Beau Bennet is fragile and not very good. It’s just a complete failure and WAY too much reliance on 87 and 71 who just can’t drag a team to a cup.

    You need three solid lines, 6 solid D. Some tough guys. The Pens have a few star D, a few star C, some nice compliments here and there, but no identity and no toughness. Shero had to go. So does Bylsma. I don’t mind keeping him in limbo (whoever said business was nice, as long as Bylsma is getting paid no one should feel sorry for him—he can always quit if he wants a new job), but eventually he needs to be canned.

    • canucks30 - May 16, 2014 at 1:46 PM

      Fair enough. However, I’d much rather have a guy like Shero who has the onions to pull off some major trades rather than a guy like Mike Gillis who is afraid to make a move and is instead committed to “the process”.

      • bobhpine - May 16, 2014 at 1:57 PM

        Uh Agreed. I don’t want either.

  5. petersteelewannabe - May 16, 2014 at 1:31 PM

    That Letang contract, whoosh-good luck dumping that…and as a Flyers fan I know all about dealing with bad contracts…

    • beergold - May 16, 2014 at 1:54 PM

      Deon Phaneuf is another good example of WTF was the GM thinking! But the Leafs have about 6 WTF contracts on the go right now!

      • canucks30 - May 16, 2014 at 1:59 PM

        You think that’s bad?

        The Islanders are STILL paying Alexei Yashin.

      • chanceoffleury - May 16, 2014 at 6:01 PM

        @canucks30

        And Dipietro until 2029. Ah, the Islanders. Every NHL team’s continuous reminder that it could always be worse. Osgood, Spezza, Luongo, Chara, and Bertuzzi were/are all overrated anyway….

        (Sorry Isles :( The silver lining is that for the first time in a long time you do seem to be headed in the right direction)

  6. canucks30 - May 16, 2014 at 1:37 PM

    Anyone else think Shero and Bylsma will end up in Washington and try to stick it to the Penguins?

    • xtrememachine1 - May 16, 2014 at 1:39 PM

      I think Shero and Trotz will end up in Washington and they will stick it to the Pens.

    • steelcity333 - May 16, 2014 at 1:40 PM

      It’s a guarantee that will happen.

    • har21441 - May 16, 2014 at 2:03 PM

      I think thats why Bylsma was not let go yet. Shero had to go now in order for the draft to not be on his watch, but Bylsma can linger for a while while they are looking for a new coach

      • canucks30 - May 16, 2014 at 2:05 PM

        If that’s the case, that’s a pretty douche move for a classy guy like Bylsma. If they don’t want him, they should let him look for work elsewhere. He did win them a Stanley Cup.

      • whammy71 - May 16, 2014 at 2:10 PM

        Reports suggest Bylsma has an attitude where he thinks he is smarter than everyone else. And they won the Cup with Therrian’s system, with a few tweets. Disco Dan even admitted such at the time. There’re wasn’t enough practice time to put in his system.

      • jernster21 - May 16, 2014 at 2:16 PM

        Reports also suggested he was getting fired today…and he didn’t.

      • 6superbowls - May 16, 2014 at 3:16 PM

        Bylsma won a cup with Therien’s team. Done nothing since but lose to lower seeded teams in the playoffs since.

      • jernster21 - May 16, 2014 at 8:14 PM

        And that team was playing so well for him that he got fired just to give them a shot at making the playoffs.

  7. steelcity333 - May 16, 2014 at 1:39 PM

    How quickly this has soured here in Pittsburgh. I’m shocking and speechless. Didn’t see this happening 5 years ago.

    • r8rbhawk - May 16, 2014 at 4:57 PM

      who saw this happening even 5 weeks ago?

  8. xtrememachine1 - May 16, 2014 at 1:43 PM

    I think this is the right move. The East is/was weak, Shero made moves to help the team win now, but that included putting themselves into salary cap hell and trading prospects for rentals. Now the cap is really tight, the farm system isn’t as good as it was and they have zero championships to show for it. I give Shero credit for gambling and playing for now, but when you gamble like that, you better win because if you don’t… well, you get fired.

  9. chrisk61 - May 16, 2014 at 1:44 PM

    the obvious point is being missed. the core problem with the pens is lack of player leadership and player toughness. as a whole the team acts like babies on the ice when the going gets rough. whining to the refs. diving. cheap shots after the whistle. and the poster boy for this behavior is syndi one hit away crosby. the second big problem is in goal. fleury is not that good. whatever he had in the 2 cup final yrs is long time. he is a shell of his former self. a wishy washy coach like bylsma is necessary because crosby is such a spoiled prima donna.

    shero and bylsma aren’t the problem, except to the extent that shero gave crosby a huge long-term deal. the core problems are crosby and fleury.

    • bobhpine - May 16, 2014 at 1:52 PM

      Seriously man. When you write stuff like Cindy (nice spelling by the way, “syndi”) you just look like a mouth breathing jerky fan. Crosby hasn’t been called for a dive in his entire career (look it up) and if there was frustration, some of it was well-founded (i.e. Staal cross-check to the head, huge increase in obstruction) escpecially since he was playing with a roster of guys who were unwilling or unable to stick up for him.

      Should Crosby shut up and play sometimes, sure. But if you think the reason they lost is because 87 “whines to the refs” well then you are just as dumb as your spelling and your reasoning indicate that you are.

      • steelcity333 - May 16, 2014 at 1:58 PM

        Of course Crosby “whining to the refs” is at the core of all their problems. Should just dump him and this team will be Cup contenders again.

      • edseverson3 - May 16, 2014 at 3:54 PM

        You sir I like.

      • c1md6 - May 16, 2014 at 5:22 PM

        You’re kidding right? Just because he’s never been called for a dive doesn’t mean that he’s not a diver. I’ve never been arrested for jaywalking but when I get off the train for work I walk right across the street without waiting everyday, does that make me not a jaywalker?

        http://m.youtube.com/watch?v=_p2hu28q3Hg

  10. barkar942 - May 16, 2014 at 1:44 PM

    “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.”
    Letang and superb should not be legally used in the same sentence.

    • petersteelewannabe - May 16, 2014 at 1:49 PM

      superb…subpar…see what I did there? ☺

  11. laxman1944 - May 16, 2014 at 1:49 PM

    Keep Bylsma….

    Trade Malkin….

    Strip the “C” from Sid……he just doesn’t get it

    Lose Neal he is just not worth the crap penalties he ALWAYS takes at the worst time, he has no control of his emotions.

    Get ready for about a 2 year rebuild

    • steelcity333 - May 16, 2014 at 1:56 PM

      Yeah, stripping the “C” from the hardest working player on the team will fix EVERYTHING. Smart thinking.

      • laxman1944 - May 16, 2014 at 3:37 PM

        Pitt. will never win another cup with Crosby as the captain.

        Hardestworking????? Don’t think so……keep drinking the juice.

        Bunch of freaking lemmings.

    • canucks30 - May 16, 2014 at 2:03 PM

      Stripping the C from Mike Modano, Patrick Marleau, Vincent LeCavalier, Eric Lindros, and Roberto Luongo sure worked out well…

      Oh wait.

    • maalea - May 16, 2014 at 2:06 PM

      You cannot take the C from Sid. Unless you want to ship him out of town, a proud player of his statue would never stand for that. Sometimes the best player shouldn’t be the capt but it’s too late to change.

      • chanceoffleury - May 16, 2014 at 6:18 PM

        Any player who thinks they *need* to have a letter on their chest to speak up or take control of a situation headed in the wrong direction doesn’t deserve the C either. If you get more leaders in the room the change in attitude will happen by itself. The thing about the best leaders is they don’t need to be given extra accessories on their jersey, or for everyone to tell them out loud how great they are. They know they’re leaders and it just happens on it’s own like second nature.

    • edseverson3 - May 16, 2014 at 3:58 PM

      You’ve been to a lot of practices? Just wondering, cause you know, the team, writers, analysts all say he is the hardest working guy on the team (except maybe Dupuis). So maybe you have inside information on how the Penguins are run and you want to give that information out.

  12. penguins87and71 - May 16, 2014 at 1:50 PM

    Ray Shero shouldn’t have got fired in my opinion, yes he made some bad signings and some bad draft picks, but so does every GM. If the Penguins are just going to promote Jason Botterill to the GM, then what’s the point of even firing Shero?

    • canucks30 - May 16, 2014 at 1:58 PM

      Wonder if the Penguins will poach Jim Benning from the Bruins. That would certainly throw a wrench into the Canucks plans.

      • mangoman1966 - May 16, 2014 at 10:24 PM

        They should pickup Gordon gallant from Montreal. Excellent coach. He would command respect or kick some ass

    • xtrememachine1 - May 16, 2014 at 1:59 PM

      Botterill is just an intern GM. He has a chance to be the next GM, but he’s not guaranteed the job. I read from Bob McKenzie that Crosby’s agent, Pat Brisson, is a possibility as the Pens new GM.

      • canucks30 - May 16, 2014 at 2:01 PM

        Hiring agents with no previous managerial experience worked out well for the Canucks…

        Oh wait.

      • maalea - May 16, 2014 at 3:33 PM

        Brisson is not going to be a GM, He could have had the Montreal job last time it was open and pulled out.

        He is making WAY TOOOO much money. He has Sid and Malkin, also Toews and Kane are coming up for huge moneyr contracts.

    • seniorteacherdot - May 16, 2014 at 2:20 PM

      I think they will find another GM, not Botterill.

  13. sgs32 - May 16, 2014 at 1:59 PM

    Agree with the guys that said that Bylsma should be the one on the lookout for a new job now, and Malkin should be headed to a new team. Also agree that its unlikely to happen.

  14. maalea - May 16, 2014 at 2:00 PM

    There is not enough “sandpaper” in this line up. Shero let quality grit players like Max Talbot walk and never replaced them with players that would sell out to win the cup.

    I’ll say it again. If 87 scores more than 1 goal in his last 17 playoff games, Shero would still have his job.

  15. penguins87and71 - May 16, 2014 at 2:02 PM

    Does anyone actually think Crosby and Malkin are going anywhere? Both have no contracts, and both love it in Pittsburgh. Crosby is the face of the franchise, so you can’t trade him, and Malkin has recently stated that if you trade him, he go back to the KHL.

    • steelcity333 - May 16, 2014 at 2:05 PM

      Neither one is going anymore as they shouldn’t.

    • seniorteacherdot - May 16, 2014 at 2:23 PM

      Crosby is the draw–the fans and opposing teams always get more seats filled when Crosby is playing. He is the money guy–you people certainly do not know what you are talking about.

      • mcphillthy - May 17, 2014 at 1:37 PM

        ^this!!! He gets more attention than any other player in the league. The NHL has sold Sidney Crosby to you. From an on ice perspective trading Crosby makes the most sense (purely because of the massive haul you would receive for him). From a front office and financial perspective this is suicide. Arenas fill when he comes to town because he is Sidney Crosby and everyone wants to have a chance to watch him play. His jersey sells in every city across the US. He won’t be traded.

    • mangoman1966 - May 16, 2014 at 10:37 PM

      You don’t trade malkin. Best player on the team

  16. hockeydon10 - May 16, 2014 at 2:36 PM

    Bad job managing the cap against the future?

    Cap Situation:
    They have 7 forwards signed for $32.4M, plus two RFAs waiting for new offers.
    They have 5 d-men signed for $17.1, with two of them on EL contracts plus one RFA waiting on his new offer.
    They have Fleury for $5M.

    That is to say for the 2014/15 season they have 14 players signed for $60.275M. Against a cap of $71.1. They have to sign three RFAs, one of which will get a little bump in pay.

    Using general terms they have two #1 centers, a solid #3 RFA center (Sutter). They have two good wingers, one legit #1 d-man, another very good d-man. They have a goalie that’s good in the regular season (not spectacular, but good) and loses his mind in a bad way in the post season (this year excluded).

    Two great centers, two good wingers, a very good d-man and a good d-man isn’t a terrible team build IF it weren’t for the cap situation. They’re handcuffed with their contracts even when compared to the upcoming bump in the cap.

    • pwshrugged - May 16, 2014 at 3:40 PM

      This. This this this! Nailed it. You have 4 guys taking up 40% of your cap, and as hockeydon says – they have 13 men signed for ’14-15 and they’re occupying…. $60M of a $70M cap. That’s complete mismanagement from the personnel/GM side, and that falls on Shero.

  17. frankiesweep - May 16, 2014 at 2:51 PM

    He never built a team for the playoffs. No grit, no guys who can play physical. No heart guys.

    It was pretty obvious. He’d always go after the big name offensive player.

  18. gbart22 - May 16, 2014 at 2:57 PM

    Blow it up :-) make the rest of us in the metropolitan happy :-) please continue over reacting like Washington and Vancouver

  19. shwatson - May 16, 2014 at 3:41 PM

    I still don’t understand how Shero just let Matt Moulson walk when he was in the origination. That ones a head scratcher.

  20. pwshrugged - May 16, 2014 at 3:49 PM

    Shero’s the one who put together a terrible roster. What’s worse for Pens fans is simply that there’s no fix for this – the Pens GM job is a wholly unattractive gig right now. I won’t go over the numbers, since they’re in posts above, but the basic jist is that for at least 3 years, 40% of the cap is occupied by 4 players. Complicating matters further, they have 13 players signed for ’14-15 for approximately $60M (of a $70M cap). This is very poor, very shortsighted GMing. It’s why Pittsburgh can ride through the regular season, but then gets crushed in the playoffs. The depth crunch kills them.

    The thing is, these aren’t problems a new GM or coach can fix. They’re problems that will last the duration of the bad contracts, since they’re guaranteed. The only real way to fix is to start trading the core away. The obvious candidate here would be Letang, but his play slipped since his stroke and with that health risk included, it’s hard to see his $7.25M/year being movable. The real question is whether or not to trade Malkin. I think Crosby is a Pen-for-life, but Malkin is the Jagr to his Lemieux, and as such, the more expendable of the two. But without any trades, this team looks like it’ll flounder for depth til some money starts to free up.

    They basically did a bad job emulating the Chicago model – whereas Chicago’s core is signed to more reasonable contracts and includes strong leaders, the Pittsburgh core is signed to overpriced contracts and doesn’t seem to have much leadership there. In the end, where Chicago has more money to spend on depth signings, Pittsburgh simply does not.

    Good luck to whoever inherits this mess. The only way out is to wait, unless they want to make some very PR-unfriendly trades in a market used to winning.

  21. ronniethec - May 16, 2014 at 7:05 PM

    Sid is a terrific player, one of the best I the game. But is he THE best? I think that is up for debate. Best scorer ….sure. Best player? Well, if I had my choice of Sid or Toews, I would take Jonathan for my team. (The Kings)

  22. slysipops - May 16, 2014 at 7:18 PM

    RAY THINKS BACK ABOUT HIS CONVERSATIONS WITH CINDY ? …………………

  23. timmons94 - May 16, 2014 at 8:07 PM

    Who cares who the best player is. Crosby gets abused all playoffs and engelland not in there to protect him. Shero has drafted worse than matt Millen. Despres scores 2 to beat baby bruins but always in doghouse when called up. A few tinks away from cup contender. I love letang. He will bounce back. Therrien was a great coach. Biggest mistake shero made was firing him. Therrien would throw up watching this team on film. We give up more odd man rushes in 5 minutes to open up game 6 then Boston does in 60 minutes

  24. bobhpine - May 17, 2014 at 12:58 AM

    Ha. The Pens job is unattractive? I suppose Florida, Vancouver (with the aging sedins and nothing else), Carolina (the amazing declining Staal brothers!) and Washington (OV, everyone’s favorite -35 player and winner of 3 playoff series…IN HIS ENTRIE CAREER) are better jobs?

    Are things ideal in Pittsburgh? No. That’s why there is a vacancy. But saying the job is unattractive is laughable. Two league MVPs, one current, a former Norris Trophy finalist, Stanley Cup winning pedigree. Yeah, who would take on such a miserable challenge, especially with a crowd that sells out 334 straight games.

    Edmonton is unattractive, Florida is unattractive. Pittsburgh is by far the best vacancy there is. Plus…there is a mandate from ownership to change the roster. So a new GM won’t be handcuffed. James Neal, Letang, Kunitz, anyone can be traded. That’s nice flexibility.

    But maybe you’re right. Maybe the best gig is returning the Florida Panthers to glory.

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