Philadelphia Flyers' Baffling Offseason Continues with Daniel Cleary Saga

Daniel WagnerFeatured ColumnistSeptember 12, 2013

Daniel Cleary has a good reason to smile, as he ended up with unexpected job security.
Daniel Cleary has a good reason to smile, as he ended up with unexpected job security.Gregory Shamus/Getty Images

It's been easy to make jokes at Paul Holmgren's expense of late, with the Philadelphia Flyers GM's willingness to make a big splash in the trade and free-agent markets coming back to bite him repeatedly.

The past week added another punch line to the repertoire of his detractors, as he reportedly signed veteran third-line winger Daniel Cleary to a three-year contract, only to have that contract turn into a professional tryout agreement then fall through altogether.

Helene St. James of the Detroit Free Press had the details of the signing on Twitter, with an odd caveat:

See, the Flyers are currently over the salary cap and couldn't actually afford to sign Cleary until they put Chris Pronger back on Long Term Injured Reserve. Officially, Cleary was to attend Philadelphia's training camp on a professional tryout agreement, while unofficially, the deal was done.

Then the reliable Elliotte Friedman threw a wrench into the works:

It's unclear what the complication is, but perhaps Cleary wanted assurances that he would still have a contract to sign if he got injured during his sham tryout. Further complicating matters is that Holmgren denied Friedman's report, telling The Philadelphia Inquirer's Sam Carchidi that Cleary is still expected to come to camp.

At this point it's nearing the definition of a debacle. The question is why Holmgren felt the need to sign Cleary to a three-year contract in the first place.

Cleary is 34 years old and, on the eve of NHL training camps, was still without a deal. Older depth players with minimal interest from NHL teams in free agency don't have a lot in the way of leverage. Considering that, $2.75 million per year is an over-payment, three years is too much term, and a no-trade clause is utterly absurd.

It's just another in a series of moves by the Flyers this offseason that have added up to a confusing whole.

After Philadelphia missed the playoffs for the first time in six seasons, the pressure was on Holmgren to turn the team around in a hurry. In typical Holmgren fashion, that meant big, sweeping changes. He bought out Danny Briere and Ilya Bryzgalov to give the team some cap flexibility, then completely erased all of that flexibility shortly after.

Actually, he erased the cap flexibility before he even had it, trading for Mark Streit's rights then signing the defenceman to a big contract before he even had space for it, meaning it couldn't even be made official until the Flyers used their compliance buyouts. It's a move that bears a strong similarity to Cleary's current situation and is emblematic of Holmgren's gung-ho approach to cap management.

In a vacuum, the Flyers' offseason acquisitions have actually made sense. Four years at $4.25 million per year for the 35-year-old Mark Streit is a little hard to swallow, but he fills a need, and the contract offer had to be competitive with the rest of the league in a shallow pool of free-agent defencemen.

They then signed Vincent Lecavalier at $4.5 million per year for five years, which is a lot when you consider he'll be 37 by the end of the contract, but it's $2 million less than they were paying the older Danny Briere.

Bringing in Ray Emery on a one-year contract at $1.65 million? That's a low-risk move that could pay big dividends if he's able to replicate his performance as a backup in Chicago.

Even Cleary is a solid and versatile winger who will fit right in on the Flyers' third line. Signing him to a short-term contract would absolutely make sense for the Flyers and would make them more difficult to play against next season.

The problem comes when you take all of these offseason moves together and put them in context with the current roster and salary cap. The Flyers will likely be a better team this season, but what's the plan for the future? Cleary, like Lecavalier, will be 37 by the end of his contract. Streit will be 39. Just how long will they perform up to the expectations of their contracts?

In Cleary's case, that's three years when a younger player like Tye McGinn or Scott Laughton might not be able to crack the lineup. Three years when he can't be traded to bring back assets if the Flyers miss the playoffs again. Three years of an aging veteran whose performance is unlikely to continue at the same level.

Cleary, Lecavalier, Streit, and Emery are all good, useful players, but each comes with an asterisk: For Cleary, Lecavalier, and Streit, it's their age and the length of their contracts. Short-term, there's a definite benefit for the Flyers, but as their age catches up to them, and the Flyers' younger players, like Matt Read, need new contracts, could each become a millstone around Holmgren's neck.

For Emery, it's the uncertainty. While he proved last year that he could be a very effective backup on a top team, the problem is expecting that same level of performance as a starter in Philadelphia. If Emery's save percentage ends up closer to his career average of .908 instead of the .922 he put up last season, it won't be much of an improvement over Bryzgalov.

Then there's the second problem: if Emery struggles, the Flyers are left with Steve Mason, who has statistically been the worst starting goaltender of the last four years. If the Flyers wanted to try to resuscitate Mason's career, bringing in a reliable veteran goaltender would make the most sense.

That isn't Emery, whose performance season-to-season has been anything but reliable. Emery's save percentage in the last four seasons has bounced from .905 to .926 to .900 to .922. Which version will show up in Philadelphia?

If the Cleary deal falls through, that opens up a roster spot for a younger player or for a veteran on a cheaper, shorter-term contract, such as Simon Gagne. If Cleary does show up to camp in Philadelphia and signs a three-year contract, Flyers fans will be left scratching their heads wondering what's next.