As teams set their rosters on the final day of September, you can only imagine what kind of thoughts are going through the minds of 30 GMs after lengthy internal debates with assistants, scouts, their kids and maybe the family dog, too.
It's easy to be outwardly optimistic. Every team is tied for first and you've likely spent the past few months talking at length about how you've re-stocked the stable through the draft and/or free agency.
But as the calendar turns and the games begin to count, the salary cap forces teams to make very hard decisions; almost every GM has at least one player/contract that keeps him up at night.
Here's a best guess as to which players/contracts have the potential to give their bosses headaches and heartburn from October onward.
Anaheim - A testament to Bob Murray's ability to remake his team in a short period of time, this roster has next to no questionable contracts. Maybe the Joffrey Lupul deal, but it looked worse in Philly where they had too many of the same type of players. Granted $4.25 million per for each of the next four years is a lot for someone who has yet to score 30 goals, but there seems to be more people believing that if Lupul is to break through, it will happen here, where he is comfortable again.
J-S Giguere's deal ($6 million) doesn't really become a problem until next year, as Jonas Hiller heads into unrestricted free agency in the summer of 2010.
Atlanta - It's not excessively high and it's only for one year, but given his recent track record and the fact he starts this season injured, Kari Lehtonen (one year at $3 million) leaves GM Don Waddell's team in a state of uncertainty in a critical position.
Oh yeah, then there's that little matter of Ilya Kovalchuk and his meter running towards UFA status in July...
Boston - Can Patrice Bergeron produce at a level conducive to a $4.75 million cap hit this year and next?
If so, GM Peter Chiarelli's deal to move Phil Kessel becomes that much easier to swallow in Bear Country.
Buffalo - Hard to pick just one. Make that impossible.
No recent numbers can justify the deals for Jason Pominville ($5.3 million for five years), Tim Connolly ($4.5 million for two), Jochen Hecht ($3.525 million for three), Toni Lydman ($2.875 million for one), and Henrik Tallinder ($2.562 million for one). But if you rewind to the spring of 2006, they all make perfect sense.
What year is it again?
Calgary - In the eyes of some, it would be the deals for Miikka Kiprusoff ($5.833 million for five) and Jay Bouwmeester ($6.68 million for five). My concern would be too many rich long-term deals that could prevent this team from compensating others in the future.
Carolina - There's a reason they've been acknowledged as one of the best organizations in North American pro sports. Fans of this team would have a tough time picking apart bad deals, because there just aren't any.
Erik Cole at $2.9 million for two more seasons may be a problem if he wears down, but it's not too heavy a burden to get out from under.
Chicago - We'll know soon enough if Cristobal Huet at $5.625 million for the next three years will work for the Hawks. If it doesn't, GM Stan Bowman's challenge of finding more money for Patrick Kane, Jonathan Toews and Duncan Keith – who are all RFAs after this season – will become that much more difficult.
Of course, it doesn't help that Brian Campbell is the highest paid player ($7.143 million) for the foreseeable future on a team where he isn't the most talented.
Colorado - The Avalanche isn't getting proper bang for the buck on the blueline, most notably in the deals for Scott Hannan ($4.5 million for two) and Brett Clark ($3.5 million for one), but if they progress through this rebuilding year at a decent pace, the club should have much more flexibility come July 2010.
Columbus - GM Scott Howson is one of my favorites for the job he's done changing the direction of this club in the past two years.
And while you could argue the overall value of deals for Kristian Huselius ($4.75 million for three) and Mike Commodore ($3.75 million for four) may be high, the fact is those two seem to be a good fit right now in Columbus.
Dallas - Has to be Brad Richards ($7.8 million for two). Here's hoping his health allows him to return to great form.
Detroit - Move along, nothing to see here.
Edmonton - He was terrific in 2006, especially in the post-season, but since then Shawn Horcoff's game has been a little off and the Oilers haven’t returned to the playoffs. There are six years to go on his deal at $5.5 million per.
Florida - It's never the fault of the player for taking the deal, so it needs to be asked again: what was former-GM Jacques Martin thinking when he signed Rostislav Olesz to a six-year extension last summer worth $3.125 million per? Yes, he's an 86-point guy, but that 86 points is over four seasons!
Los Angeles - After so many down years, the Kings can afford to carry some overpaid veterans for the short term. But when the blueline matures – which it might rather quickly – the Rob Scuderi deal ($13.6 million over four years) could become a little onerous.
Minnesota - GM Chuck Fletcher is only a few months into the transformation of the Wild, so for this year the hope must be that pending UFAs Owen Nolan, Petr Sykora, Kim Johnsson and Marek Zidlicky have solid enough seasons to push the club back into a playoff spot. Next summer, Fletcher should have more money to work with, making them an organization worth watching.
Montreal - The dollars are big, the terms are long and patience is short in Montreal. All season – and for the next four years after this one – all eyes will be on Scott Gomez ($7.357 million for five years), Brian Gionta ($5 million for five years) and Mike Cammalleri ($6 million for five years).
Nashville - Entering his 10th NHL season – and only once having gone north of 50 points – David Legwand is struggling to live up to the contract extension that has him locked in for five more years ($4.5 million per).
New Jersey - Last summer, Brian Rolston’s return to New Jersey seemed like a great fit. But at age 36 and with three years at $5 million to go, Rolston needs to be 100 percent healthy if the Devils are to get a significant return on this massive investment.
Islanders - Welcome to Year 4 (of 15) of the Rick DiPietro deal. And they're still paying Alexei Yashin for six more years!
Rangers - Too much R and R (Redden and Rozsival make a combined $11.5 million) on the blueline.
Ottawa - Does anyone else still need convincing on Pascal Leclaire before his $3.8 million cap hit is justified?
Philadelphia - See Chicago. Highest paid player (Daniel Briere, $6.5 million for six more years) is not their best.
Phoenix - Player salaries are the least of their issues right now.
Pittsburgh - GM Ray Shero is a magician. And for his next trick he'll find a way to secure Kris Letang and Sergei Gonchar beyond this season. Has anyone heard if the salary cap is coming down?
San Jose - All of them! Really, who isn't under the microscope in San Jose this year?
St. Louis - Like so many teams, the contracts aren't a concern if everyone stays healthy. But deals for Paul Kariya ($6 million for one), and Eric Brewer ($4.25 million for two), among others, sure sting when they can't maximize their potential.
Tampa Bay - Like the Islanders did with their goaltending in signing Dwayne Roloson and Martin Biron, GM Brian Lawton did his best to ensure injuries to the blueline won't completely derail another season. All in all, mostly good contracts here…health permitting.
Toronto - The Leafs re-joined the spenders club this off-season and now you don't hear nearly as many people talk about the salaries of Jason Blake ($4 million for three) and Jeff Finger ($3.5 million for three).
Given how the Leafs have admitted to be willing to bury underperforming big-money players in the minors, GM Brian Burke has far fewer cap worries than his peers.
Vancouver - A strong summer for GM Mike Gillis leaves the Canucks with a well-balanced payroll. Staying beneath the cap and still having room to maneuver at the deadline may be his biggest challenge.
Washington - Two words: Michael Nylander ($4.875 million for two).
Brian Duff is a host of On The Fly on the NHL Network. Like his minor hockey days (playing goalie, defense and forward) his broadcasting career has been all over the map. In radio and TV from Medicine Hat to Edmonton, Toronto to Ottawa and back, Brian has been with the NHL Network since 2007 and has been covering the game for nearly 15 years. Read more of his THN.com Blog HERE.