Pre-July 1 Conundrum: What will Ray Shero do about Jaromir Jagr, Tyler Kennedy and Pascal Dupuis?

With the 2011 NHL draft in the rearview mirror, Pittsburgh Penguins management has to quickly shift gears even before unrestricted free agency opens up this Friday.

The right wing position on the organization's depth chart is practically empty.  Evgeni Malkin and Jordan Staal both figure to slot into center ice, and the team's best wingers, Chris Kunitz and James Neal, are natural on the left side. 

Tyler Kennedy, coming off a good year, is still an unknown in a full-time top six role.  His agent is looking to cash in on a 21 goal, 45 point season with a strong case for arbitration that could easily see him awarded a salary of $2+ million dollars per year.  Pascal Dupuis, serviceable though not terribly productive in a top six role, is an impending unrestricted free agent.  Ar Dupuis' age, this is likely his last chance to sign a top dollar contract, and one for three or more years, if he can get it.

Thanks to the salary cap going up to a top limit of $64.3 million dollars, General Manager Ray Shero has about $8 million in space, give or take a little.  Right wing is the glaring need, but he also needs to add a fourth liner and a forward with penalty killing skills.  Dupuis and Maxime Talbot were two of the team's heaviest lifters on the PK, both are unrestricted and Talbot seems all but gone. 

Jordan Staal and Craig Adams will be staples of the PK unit, with Matt Cooke too.  But Cooke has an extreme question mark on whether or not he can adapt his game effectively to stay in the lineup without making a dangerous/dirty hit that will surely draw another severe (and possibly career ending) suspension.  Even if he amends his game, that's three PK'ing forwards for a team that usually rolls with 5-6.  Sidney Crosby could take some of the burden, but it remains to be seen how wise it would be to put him in a regular non-offense, injury prone role that will zap more of his energy away from what he does best, creating offense.  Guys like Kunitz, Neal and Mark Letestu could also be options to take PK shifts, but not necessarily great ones in the all-around scheme of things.

All these moving pieces create a lot of uncertainty before the storm.  But the storm is about to hit and decisions need to be made.

More, after the jump..

Somewhat surprsingly, coach Dan Bylsma has been publically positive towards adding Jagr.  Shero, on the other hand, has been a little more frosty, in not yet making a contract offer.  The negatives are clear: at 39/40 years old and three years removed from the NHL, how much Jagr has left is an honest question.  How his attitude on and off the ice would fit in with the young, uptempo, north/south Penguins team is another legitimate concern and not a perfect match.

A lot has been made of the turmoil Jagr has brought: he famously has been cranky (at best) about systems he doesn't like or fit, and he's not a natural fit for Pittsburgh's current style.  But let's not forget Mario Lemieux used to regularly over-ride coaches- including no less than legendary Scotty Bowman- for ideas that he did not like.

Jagr, from all accounts, seems genuine in his interest to return to the NHL, and for a reasonable price of $2-3 million dollars on a one-year contract.  Jagr's short list of teams is Pittsburgh, Detroit and perhaps a "mystery" team which most believe to be Montreal.  From his contract demands, he's looking to join a contender and not just coming back for a pure paycheck.

Tribune-Review writer Rob Rossi laid out the cases of Jagr, Dupuis and Kennedy with the knowledge he has.  Rossi's plan (in a nutshell): try to sign TK by Wednesday, or deal him if the demands prove too high.  Offer the valuable and versatile Dupuis a three year deal for $1.7 million per year, a deal Rossi thinks that Dupuis is likely to accept.  Then make a firm one year offer for Jagr and see if the Czech will follow his heart back to Pittsburgh where his career started.

I would echo many of these points.  First, Jaromir Jagr must be dealt with.  If Shero drags his feet, JJ could easily decide to go to a veteran-laden Detroit team that probably fits his game more.  The Pens should make their interest clear for Jagr, and if the price is under $3 million, there's enough room under the cap to make it work.

Secondly, try to lock up Pascal Dupuis.  The cap has been continually rising every year, and a ball-park figure of $1.75 million for three years makes sense.  Dupuis, on a 3rd line with Cooke and Staal, would be an ideal fit and gives the Pens the penalty killer they need.  If he wants more money or longer term, move on, but it's reasonable to believe it'll work.

Finally, there's a little more time to deal with Tyler Kennedy.  Even as a restricted free agent, TK is unlikely to draw an offer sheet from another team.  Arbitration cases won't happen for weeks, which means the team will know Jagr and Dupuis' statuses by then.  If one or both veterans sign on, walking away from an unfavorable arbitration case makes a lot more sense, being as the Pens right wing situation will be secured.  If the Pens need Kennedy, they would have enough space to keep him.  And, hopefully, in between now and the arbitration hearing, TK might be able to be signed for a friendlier price.

Finally, for the fourth line, the Pens could promote Joe Vitale, an energy center not unlike Talbot. Vitale is better on faceoffs than Talbot and at just $512,000 Vitale is a friendly cap number and would allow Craig Adams to shift to a more natural role of 4th liner right winger.  If Vitale doesn't have a good training camp, other young players like Nick Johnson or Eric Tangradi would be nice NHL options as well.

The Penguins have a lot of moving pieces and a lot of different scenarios that will play out before and after July 1.  The time to set the wheels in motion are now, and the decisions made in the next few days will ultimately shape the 2011-12 roster.