NHL Free Agency: A Decade of Decisions

I was on vacation last week, but whenever I flipped on a TV or checked Twitter, every sports fan I saw was going nuts about some sort of big free-agency signing. I checked the hockey transactions when I got back, and I’ll be honest: I didn’t really see what all the fuss was about. I guess everyone was just really excited about Bryan Lerg.

But now that I’m back, I figured today would be a good day for a look back on NHL free agency. And not just this year’s edition — I want to go all the way back over the past decade. After all, this summer marks the 10th offseason of the NHL’s salary cap era. If you remember, that era kicked off in 2005 with a brand-new CBA that, among other things, allowed players to earn unrestricted status much quicker than under the old rules. That was supposed to make free agency a more important part of building a contender, as more big names hit the market in their prime. Of course, it hasn’t quite worked out that way.

So let’s take a look back through that first decade of salary cap free agency and use the powers of hindsight to figure out which were the best and worst deals handed out each year (from the teams’ perspective). A few quick ground rules: First of all, we’re dealing only with players who changed teams; extensions feel like a different category. And we’re focusing on the big-dollar deals here, since we don’t want the “best” category to be overrun with minor deals for players who went on to unexpectedly develop into stars.

Let’s start at the beginning: August 2005, when the league emerged from a yearlong lockout and teams got their first crack at a new world of free agency.


The 2005 offseason was a strange one. The lockout ended in July, and teams were given the opportunity to use unlimited compliance buyouts to get under the new salary cap. In theory, that should have flooded the market. In reality, teams largely played it cautious.

Best: Scott Niedermayer, Mighty Ducks, $27 million over four years

This one’s not an especially tough call, as Brian Burke and the Ducks nabbed a reigning Norris winner and future Hall of Famer who still had plenty of good years left. (They also had an advantage over other teams in the form of Scott’s brother Rob, who was already on the roster. The two had always wanted to play together.)

Scott Niedermayer posted a career high in points in his second season in Anaheim. When he was joined by Chris Pronger for 2006-07, the dominant duo gave the Ducks the franchise’s first Stanley Cup.

Worst: Alexander Mogilny, Devils, $7 million over two years/Vladimir Malakhov, Devils, $7.2 million over two years (tie)

You see what I mean about playing it cautious — while these two deals were mistakes, they weren’t the kind of long-term cap crushers we’d see in later years.

But yeah, it was a bit of a rough offseason for the Devils, who used the cap space saved by Niedermayer’s departure to sign a pair of bad deals. Mogilny lasted only half a season before being buried in the minors and eventually being placed on the injury list. Malakhov was sent home around the same time, and was eventually dealt to the Sharks in a deal that saw the Devils send a first-round pick to San Jose just to get rid of his cap hit.


With one salary cap season under their belts, NHL GMs started getting more aggressive. The results were mixed, although most of the biggest deals signed this summer — like Brad Richards, Patrik Elias, Marty Turco, Bryan McCabe, and, most memorably, Rick DiPietro — were teams re-upping with their own players.

Best: Zdeno Chara, Bruins, $37.5 million over five years

Another easy call, and arguably the last big-time free agency deal that actually worked out well. The Senators famously chose to keep Wade Redden and let Chara test the market, a decision that was an utter disaster in hindsight (but, despite what you may remember, not all that unthinkable at the time). The Bruins swooped in and signed him to one of the league’s richest deals and he’s been their top defenseman ever since, winning a Norris Trophy and a Stanley Cup along the way.

One largely forgotten piece of this story: Bruins GM Peter Chiarelli had been hired but had not yet officially started work for Boston when the Chara deal was signed, as his previous team had insisted that he not leave until July 15. That old team: the Ottawa Senators. Was Chiarelli secretly involved in making the Chara deal anyway? We may never know, but let’s just say that Senators fans have their suspicions.

Worst: Ed Jovanovski, Coyotes, $32.5 million over five years

For the second straight year, NHL GMs managed to avoid signing any truly disastrous deals. Jovanovski had just turned 30 and was already battling injuries when the cash-strapped Coyotes made the curious decision to give him a deal that was just short of Chara’s. But it’s not like the deal was awful — he played well enough while finishing out the full deal in Arizona, and he’s even still (technically) active today.

Hey, maybe NHL GMs aren’t so dumb after all!


Huh. Hold that thought. This is the year things started getting ugly.

Best: Brian Rafalski, Red Wings, $30 million over five years

Rafalski didn’t come cheap, but he gave the Wings everything they could have hoped for. He finished in the top 10 in Norris voting in each of his first two seasons and was a key component of Detroit’s Stanley Cup win in 2008. And when his production started to decline, he unexpectedly retired in 2011 rather than cash in on the final year of his deal.

Worst: Scott Gomez, Rangers, $51.5 million over seven years

There’s no shortage of candidates from the 2007 offseason. The Flyers gave Danny Briere eight years with a $6.5 million cap hit. The Rangers gave Chris Drury five years, worth more than $7 million a season. And we haven’t even mentioned Sheldon Souray, Michael Nylander, or Jason Blake.

But it was Gomez who became the poster child for awful free-agent deals, thanks to plummeting production that eventually saw him suffer through a historic scoreless streak before getting bought out. Of course, that didn’t happen in New York; the Rangers actually got two decent years out of Gomez before somehow offloading him to the Habs in a deal that landed them Ryan McDonagh.

Worth noting: This was the first year in which we saw GMs start to experiment with front-loaded deals, although not to the extremes that we would in later years.


After all the misfires in 2007, you’d think that NHL teams would get cold feet about handing out massive deals a year later. You would be wrong.

Best: Marian Hossa, Red Wings, $7.45 million for one year

This deal ended up becoming a punch line; Hossa spurned 2008 runner-up Pittsburgh to join the champion Red Wings, only to see the two teams meet again in 2009 with the Penguins winning. But playoff results aside, this was a great deal for Detroit, who got an elite player in his prime on a low-risk one-year deal.

Worst: Wade Redden, Rangers, $39 million over six years

With apologies to Brian Campbell’s massive $57 million deal, the Jeff Finger debacle, and the unmitigated disaster that was Sean Avery’s stint with the Dallas Stars, Redden easily takes 2008’s undisputed crown.

The deal seemed curious when it happened, since Redden was coming off a rough year in Ottawa. Over time, it quickly descended into farce. Redden lasted just two years in New York before being buried in the minors, a victim of a cap loophole that essentially ended his NHL career; he was finally, mercifully bought out after the 2012 lockout, and had a brief comeback attempt with the Blues and Bruins before retiring.


We’re fully into the “front-load the hell out of contracts in blatant violation of the spirit of the salary cap” era. For reasons nobody fully understands, the NHL continued to approve these deals, only to retroactively change the rules in 2013 to punish them.

Best: Marian Gaborik, Rangers, $37.5 million over five years

By 2009, the concept of the “best” big-dollar free-agent deal was relative, since they’re almost always terrible. But I’ll go with Gaborik here, partly because I feel like Rangers fans who haven’t roundhoused their monitors by now could use some good vibes.

Gaborik didn’t come cheap, and he wore out his welcome in New York before the five years were up. But he did give the Rangers a pair of 40-plus-goal seasons over the course of the deal, and as this year’s playoffs showed, he was still a top player by the end of it. That’s not bad, and by 2009 “not bad” was pretty much the best we could have hoped for.

Worst: Marian Hossa, Blackhawks, $63.3 million over 12 years

As much as I’m tempted to give this spot to Mike Komisarek’s awful deal with Toronto, I’m going to go with what I suspect is a more controversial pick: Hossa’s monster contract with the Blackhawks.

Hawks fans could argue that this can’t be considered a bad contract because Chicago won two Cups in its first four years. But the deal goes on until 2021, at which point Hossa will be 42, and it’s so comically front-loaded that the cap-recapture penalties are potentially huge.

The Hawks didn’t know about that last part when they signed the deal, of course, because again, the NHL changed the rules on everyone years later. But in hindsight, the team must wish it had just swallowed the higher cap hit to get a shorter deal done. Could they have still won those Cups if they had? Your answer to that question probably goes a long way toward deciding if you agree with this pick.


This was the year of the ridiculous Ilya Kovalchuk contract, which doesn’t qualify for our list (since it was a re-signing) but still deserves a mention just for the $100 million price tag, 15-year term, and the even crazier initial version of the deal that cost the Devils a fine and a first-round pick that Gary Bettman eventually wimped out on and gave back.

Best: Dan Hamhuis, Canucks, $27 million over six years

Aside from Kovalchuk, the 2010 UFA class was decidedly sparse — by this point, the trend of GMs locking up their own players well before free agency had been clearly established. Most of the summer’s attention went to a collection of midtier defensemen like Paul Martin, Sergei Gonchar, and Hamhuis. The latter gets the nod here; he’s not exactly a bargain, but he’s been a solid addition to the Canucks lineup, even making the 2014 Canadian Olympic team.

Worst: Anton Volchenkov, Devils, $25.5 million over six years

Volchenkov had drawn all sorts of “defensive defenseman” raves in Ottawa, and cashed in on that reputation with the Devils. After four increasingly disappointing seasons in New Jersey, he was bought out a few weeks ago.


Brad Richards at $60 mllion, Ville Leino at $27 million, Ilya Bryzgalov at $51 million … we’re now solidly into “You know, maybe the smart move is to just sit out free agency every year” territory.

Best: Uh … pass?

Seriously, I’m kind of stumped here. Jaromir Jagr’s one-year deal with the Flyers was fine, and Mike Smith worked out great for the Coyotes, but both of those deals came cheap. Beyond that, just look at this mess. Free agency was awful in 2011.

Worst: Ville Leino, Sabres, $27 million over six years

I know, I know, you’re expecting to see Bryzgalov’s nine-year, $51 million monstrosity here. But that deal was actually signed a week before free agency, after the Flyers acquired his rights in a trade. Which is a shame, because the deal may go down as the worst in NHL history.

It’s not just that Bryzgalov lasted only two shaky years in Philadelphia before receiving a comical $23 million buyout that will see the Flyers cutting him checks until 2027. The team also had to clear out cap space to make the deal happen, and that led to them trading popular franchise players Mike Richards and Jeff Carter on the same day the Bryzgalov contract was signed. Those two were last seen celebrating their second Stanley Cup title in Los Angeles. Bryzgalov was last seen splitting time between the Oilers and Wild, and has yet to find a new home in this offseason’s market. Again: $51 million contract; Richards and Carter; $23 million buyout through 2027. The aristocrats!

Wait, where were we? Oh, right, Ville Leino. That deal was bad too. Not Bryzgalov bad, but bad.


This would be the last round of free agency under the initial salary cap CBA, as well as the one that set the table for the lockout that would wipe out half the following season.

Best: P.A. Parenteau, Avalanche, $16 million over four years

Parenteau put up almost a point per game in his first season in Colorado, and was decent last year in limited action. At a $4 million cap hit, this deal was not terrible. Does “not terrible” really qualify a contract for consideration in the “best” category?

[Checks back over previous few years.]

Yes. Yes, it most certainly does.

Worst: Ryan Suter/Zach Parise, Wild, $98 million over 13 years (each)

Yes, I know, Minnesota fans are going to yell at me because Parise and Suter are both good players. And today, the Wild are probably thrilled to have them both in the lineup, even at cap hits north of $7 million. But what about in a few years? Or a few years after that? Or a few years after that, and we can keep doing this for a while because these deals go on forever?

Suter’s and Parise’s deals will always be remembered as the last of the great super-long-term, ridiculously front-loaded contracts that came to mark this CBA. They looked like big gambles at the time; today, with cap-recapture penalties looming, they seem ludicrous.

(And let’s be sure to award some bonus points to Wild owner Craig Leipold for signing these deals, then being one of the key owners pushing for the lockout that followed a few months later.)


This was the year in which Stephen Weiss, Mike Ribeiro, Vincent Lecavalier, and Ryane Clowe all signed terrible, horrible, awful deals that didn’t even get a sniff of the “worst” category. NHL GMs are certifiably insane.

Best: Jarome Iginla, Bruins, $6 million for one year, sort of

This one comes with a bit of an asterisk, as the Bruins used a bonus-laden structure to drive down the cap hit (although only temporarily; they’ll pay a penalty next year). Still, Iginla provided yet another 30-goal season and was willing to do it on a short-term deal in an attempt to win a Cup ring. It didn’t work out that way, but the deal itself wasn’t a disaster. In the 2013 free-agency market, that made it a borderline miracle.

Worst: David Clarkson, Maple Leafs, $36.75 million over seven years

I don’t want to talk about it.


Two weeks into the free-agency season, most of the big names have signed. None has played a game with his new team, of course, which makes this section a little tricky. Will I sneak in and edit my picks in shame once I’m proven wrong? Check back in a few months to find out!

Best: Paul Stastny, Blues, $28 million over four years

This has serious potential to blow up in my face, but screw it — I like Stastny a lot, and I think the Blues did a great job of landing him on a relatively short deal.

Yes, $7 million seems like too much (although I’d argue not by much), and they probably could have gotten him to agree to a more cap-friendly deal along the lines of six years at $6 million. But that’s exactly the sort of mistake that too many teams keep making — trading off term for cap hit, on the unspoken assumption that the deal’s worst years will be some other GM’s problem.

Instead, the Blues stepped up to pay a fair price without tacking on a bunch of guaranteed pain at the end of the deal. I could end up looking bad on this one, but I say it was a good call. And given our stated preference for big-dollar contracts in this post, it’s enough to give Stastny’s deal the edge over shorter, cheaper signings like Brad Richards and Christian Ehrhoff.

Worst: Dave Bolland, Panthers, $27.5 million over five years

There’s a great case to be made for Brooks Orpik, who signed an identical deal with the Capitals. But after going back and forth a few times, I’m handing this year’s crown to Bolland and the Panthers.

Why? Because this is the deal that caused the Toronto Maple Leafs to say “No, that’s too much money to pay for a gritty third-liner.” Think about that for a second. Until two weeks ago, Maple Leafs fans didn’t even realize that was possible.

Look, I like Bolland. He’s a solid defensive center, he can kill penalties, he sounds like a decent enough teammate, and he did swat a puck into an open net after it bounced right to him at a crucial moment that one time. He’s also nearly 30, hasn’t cracked 40 points since 2009, and is still rehabbing the sort of major leg injury from which some players never seem to fully recover.

Despite all that, the Maple Leafs were more than willing to throw big money at him. But the Panthers threw even more. There’s no way that turns out to have been a good idea.

Filed Under: NHL, NHL Free Agency

Sean McIndoe ’s work can be found at Down Goes Brown. When he's not writing, he makes hockey jokes on Twitter at @downgoesbrown.

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