On Tuesday, San Jose Sharks defenceman Brent Burns signed an eight-year extension that will pay him $64 million and carry an $8 million cap hit.

It’s a huge contract — the biggest since Jamie Benn‘s deal this past summer and almost certainly the largest that we’ll see signed during the 2016-17 season.

But none of that really matters.

What fans want to know about the Burns contract is this: Is it a good deal or a bad one?

We can’t know for sure yet, although we can already compare it to those of his peers.

The early consensus seems to point to a deal that carries a fair cap hit for a player of his calibre, but with a length that makes it a high-risk gamble on a player who’ll have turned 40 by the time the contract expires. Only time will tell whether the deal ends up being worth the risk for the Sharks.

But even if the Burns deal does end up backfiring for San Jose, they’ll have plenty of company. The NHL is littered with bad contracts; every team has at least a couple.

Twelve seasons into the salary cap era, you’d think general managers would be learning how to avoid some of these mistakes. But we still see them made all the time, and they usually fall into one of a few categories.

So today, let’s look through those categories, and see if we can give our friends in NHL front offices some tips on avoiding them.

—

THE JULY 1 MELTDOWN

The contract: This is the most obvious category, with a big chunk of the league’s worst deals falling into it.

To put it simply, NHL GMs do their worst work when unrestricted free agency opens on July 1. You target a player, the bidding war starts, and next thing you know you’re paying way more than you meant to.

We’ve actually seen a drop in truly terrible July 1 deals over the years, largely thanks to the new negotiation window that opens up a few days in advance. But we still see more mistakes made on that one day than any other.

Recent examples: Scott Gomez. Wade Redden. Danny Briere. Brad Richards. Stephen Weiss. Loui Eriksson. Andrew Ladd.

How to avoid it: Don’t let anybody in the front office anywhere near a phone on July 1.

Seriously, how long will it be before some GM (or owner) makes this an official team policy? Every year, we see teams pay through the nose for players on July 1, and every year we see great bargains still sitting around a few days later for a fraction of the price.

Every GM thinks they can be the one who makes the smart deal on UFA day, but history has shown us that most of them are wrong.

—

PAYING FOR INTANGIBLES

The contract: Look, intangibles exist. Just because something is hard to measure doesn’t mean it’s not important, and that’s especially true in a sport like hockey.

Leadership matters. So does work ethic. And yes, even heart. But the waiver wire is filled with guys with plenty of heart and leadership. Paying top dollar for it rarely works out well.

Recent examples: Ryan Kesler. Ryan Callahan. Casey Cizikas.

How to avoid it: If your star player is also your hard-working leader, then great, go ahead and pay him. But if not, smart GMs will focus on pouring as much talent as possible into the core and save the intangibles for the (far cheaper) depth pieces.

If there are two mistakes on this list that can torpedo a team’s cap situation, it’s paying for intangibles and the July 1 meltdown. In fact, it’s hard to even imagine anything worse…

Oh, hey, what’s this next section…

—

THE JULY 1 MELTDOWN THAT INVOLVES PAYING FOR INTANGIBLES

The contract: Oh no.

Recent examples: Dave Bolland. Deryk Engelland. Ryane Clowe. Dale Weise. Clayton Stoner. Stephane Robidas. And the worst of them all: David Clarkson.

How to avoid it: If anyone in your front office so much as utters the words “compete level” on July 1, fire them immediately.

THE NO-CHOICE EXTENSION

The contract: He’s your star player, and has been for years. Now, with UFA on the horizon, it’s time to pay up.

Will the contract be too expensive? Probably. Will it be too long? Almost certainly. But what are you going to do, let him walk for nothing? Trade him at a steep discount? No. You’re going to open the vault.

Recent examples: If the Burns deal ends up looking bad, this will be the category it lands in.

Anze Kopitar, Jonathan Toews, Patrick Kane, Dustin Byfuglien and Jamie Benn could all wind up here too someday, although all of those deals are fine for now.

But some other contracts in this category already look bad, including Dion Phaneuf, Mike Smith, Bobby Ryan, Travis Zajac, Marc-Andre Fleury and (depending on who you ask) Jonathan Quick.

How to avoid it: In a league where “never let a star get to free agency” has all but become law, these deals are almost impossible to avoid. The best you can hope for is that teams are brutally honest about who’s a star and who isn’t – and that fans won’t riot if a good player is allowed to walk rather than being handed superstar money.

THE SHINY NEW TOY

The contract: Congratulations! You’ve just pulled off a major trade to bring a new star to town, and everyone’s very excited.

There’s only one problem: He needs a new contract. Whoops. Better take care of that ASAP.

Recent examples: Jordan Staal. Jason Spezza. Ilya Bryzgalov (sort of). Brandon Sutter. Maybe Ryan O’Reilly or Dougie Hamilton, but the jury’s still out on both.

And of course, the mother of all bad contracts: Alexei Yashin.

How to avoid it: It would be easy to say “Don’t acquire players who need new contracts,” but half the time that’s the only reason a top-tier talent has become available.

These sorts of deals can put GMs in an almost impossible spot. You’ve just given up assets to bring a guy to town, and probably held a fancy press conference to tell your fans how fantastic he is. Are you really going to turn around and tell his agent that you don’t think he’s worth top dollar?

THE LOYAL SOLDIER

The contract: Deep down, you know the player’s not worth it. On paper, it’s not even really close. But this guy has been a part of the team forever. He bled for you. Maybe he even helped you win a Stanley Cup or two. And the fans love him. If you’re going to overpay anyone, isn’t this the guy who deserves it?

Recent examples: Dustin Brown. Cam Ward. Bryan Bickell. Dustin Brown. Justin Abdelkader.

Did we mention Dustin Brown? Good lord, that contract is awful.

How to avoid it: You hear it all the time: sports in a business. You have to put personal feelings aside and make the right move, even if that means walking away from a guy everyone says you have to re-sign.

The best GMs can be heartless when they need to be. But it’s easier said than done.

—

THE OFFER SHEET

The contract: The dreaded offer sheet is one of the most powerful tools available to any GM looking to improve his team by plucking a top RFA talent away from a competitor.

By targeting vulnerable opponents, a smart GM can instantly upgrade his own team, often by acquiring a player who may just be entering his best years. It’s a formidable weapon — one that any GM doing his job would be eager to wield.

Recent examples: Shea Weber. And… that’s pretty much it. Huh. Isn’t that weird.

How to avoid it: Remind your fellow GMs that you’ve all just decided not to do this, apparently.

—

SHOULD HAVE LISTENED TO YOUR ANALYTICS GUY

The contract: Hey, did you hear somebody babbling about possession numbers and PDO and regression to the mean?

Me neither. Pass the pen.

Recent examples: A whole lot of the contracts we’ve already mentioned could fall into this category too.

There’s the sub-group of guys who got big money off of a one-year shooting percentage bender, like Ville Leino, Nick Foligno, Jason Blake and Matt Beleskey.

Then there are the possession black holes on the blue line, like Andrew McDonald, Brooks Orpik and Dan Girardi.

(Kris Russell, too, except for once everyone did listen to the analytics guys and he wound up with a contract that was actually reasonable.)

How to avoid it: This is going to sound crazy, but hear me out: Maybe listen to your analytics guy.

THE NOSE DIVE

The contract: In a sense, this is the worst-case scenario for a GM. Every big contract involves risk, and you have to weigh the odds that it will be worth it in the long run.

But sometimes you sign a guy with a proven track record of consistent production who should still have plenty of good years left, and he’s just never the same player.

Maybe he gets hurt, maybe the money affects his work ethic, or maybe it’s just terrible timing. But for whatever reason, his play falls off a cliff, and now you’re screwed.

Recent examples: Vincent Lecavalier. Dany Heatley. Nathan Horton. Chris Pronger. Kari Lehtonen. Joffrey Lupul. Martin Havlat. Rick DiPietro, sort of, although the Islanders were paying for potential as much as anything he’d actually done yet.

And maybe the most predictable drop-off of all: Alexander Semin.

How to avoid it: There’s no way to avoid bad luck, and sometimes you’re just going make a smart deal and just land on the bad end of the probability curve. But it helps if teams understand what those curves really look like — you still occasionally see GMs who seem to think players are hitting their prime in their late 20s when the evidence shows that’s just not the case anymore.

—

THE SUPER LONG-TERM DEAL THAT MADE SENSE AT THE TIME BUT LOOKS BAD NOW

The contract: Finally, this type of contract was essentially outlawed under the new CBA, but there are still enough of them kicking around the league that they’re worth mentioning.

Many of these were perfectly good deals when they were signed, and some will ultimately provide positive value over the full length of the contract. But we knew the later years were going to be ugly, and that moment has arrived.

Recent examples: Marian Hossa. Roberto Luongo. Brent Seabrook. Henrik Zetterberg. Ryan Suter and Zach Parise soon, if not already.

Strombone on Twitter



How to avoid it: Lock out the players for half a season to get a new CBA that prevents you from making this mistake.

Oh, you did that already? Cool.