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Down Goes Brown: The five worst free agent signings of the past 20 years

Time to look back at some cautionary examples of how quickly a big free agent deal can go bad, especially if you're the Rangers.
The Hockey News

The Hockey News

Free agency opens on Friday, as teams will be officially allowed to sign players on the open market, and fans around the league should be excited. No, wait, excited isn't the right word. What's the one I'm looking for? Terrified. That's the one. You should all be terrified. That's because, despite the occasional success story, NHL teams tend to be terrible at signing free agents. They can't help themselves. And it rarely takes long for the initial excitement of a big signing to give way to the realization that a team has just handed out too much money for way too many years. As we count down to Friday's deadline, let's take some time to look back at some cautionary examples of how quickly a big deal can go bad. Here are my picks for the five worst unrestricted free agency signings of the past two decades.

5. Teemu Selanne and Paul Kariya, Colorado, 2003

The deal: The two friends (and former Ducks teammates) shopped themselves as a tandem deal, eventually signing

cheap one-year contracts with the powerhouse Avalanche. How cheap? Selanne took a pay cut to $5.8 million after declining a $6.5 million option in San Jose. But that was nothing compared to Kariya, who took just $1.2 million after making $10 million the year before in Anaheim. Both players could have made much more elsewhere, but they were chasing their first Stanley Cup rings, and joining Joe Sakic, Peter Forsberg and an already loaded Avalanche team seemed like the best way to do it.

Why it made sense at the time: Are you kidding? Go back and re-read those details – it was foolproof. When the deals were announced, hockey fans everywhere pretty much threw up their hands and conceded the 2004 Cup to the Avalanche.

How it ended: In what may stand as the NHL's greatest example of a

can't miss move somehow missing, both Selanne and Kariya were busts in Colorado and the Avalanche lost in the second round. That latter part wasn't a huge shock – while the Avs still had most of their big names from their Cup years, they'd lost Patrick Roy to retirement in the offseason, and winning a title with David Aebischer never felt like a safe bet. But the real surprises were Kariya and Selanne, neither of whom cracked 40 points. When Steve Konowalchuk is outscoring both of your sure-thing signings, it's safe to say that something has gone terribly wrong.

4. Ville Leino, Buffalo, 2011

The deal: Coming off a career-best 53 points, the 27-year-old winger landed a six-year, $27 million deal from the Sabres.

Why it made sense at the time: After years of drifting into small market status, the Sabres had a rich new owner and were ready to spend some of Terry Pegula's money. (They also gave Christian Ehrhoff a 10-year, $40-million deal.) Leino had just posted a career year while helping the Flyers make it to the Cup final, and it was time for the Sabres to make some noise.

How it ended: Leino was a massive bust in Buffalo; his eight goals and 25 points in year one ended up being by far his most productive season as a Sabre. He missed almost all of year two of the deal, then went the entire 2013-14 season without scoring a single goal before being mercifully bought out. (By the way, Leino wasn't close to the worst contract handed out during the summer of 2011. That honor would go to a deal you're probably expecting to see on this list: Ilya Bryzgalov's $51-million deal with the Flyers that led to a massive buyout just two years later. But that one wasn't technically a free agency deal, since the Flyers had acquired his negotiating rights and signed the deal before he reached the open market on July 1. )

3. Mark Messier, Vancouver, 1997

The deal: In a move that came as a mild surprise, Messier left the Rangers to sign with the Canucks during the 1997 offseason, signing a five-year deal worth $30-milliom.

Why it made sense at the time: Messier was well past him prime – he was 36 when the deal was signed – but was still a very productive player and was widely regarded as the best leader in pro sports. The idea of him centering Pavel Bure and Alexander Mogilny to form the most unstoppable line in the league was hard to resist.

How it ended: Well, first we have to mention how it started: With Messier taking the captain's "C" from fan favorite Trevor Linden. After a slow start, the Canucks doubled-down on the 1994 Rangers nostalgia by hiring Mike Keenan, and it wasn't long before the beloved Linden was sent packing to the Islanders. More than a few fans (and

at least one player) put the blame for that solidly on Messier. Messier went on to score a disappointing 60 points in his first year in Vancouver, then failed to hit even that total over the next two seasons. He was bought out in 2000 and rejoined the Rangers for four more years, later taking the Canucks to court

over deferred money. The rest of us agreed to never speak of any of this again. Fun side note: To this day, any Canucks fan you meet will become irrationally angry if you casually slip Messier's name into a conversation.

2. David Clarkson, Toronto, 2013

The deal: One of the biggest fish in a very small 2013 free agency pool, Clarkson landed a six-year, $37-million deal from Toronto. As an added bonus, the Leafs structured the contract to be

virtually buyout-proof.

Why it made sense at the time: It didn't, as virtually

every smart observer

immediately pointed out. Even GM Dave Nonis all but wrote off the second half of the deal with his infamous

"not worried about six and seven" quote. But the Maple Leafs were in the midst of one of the

most ridiculous offseasons of all time, one in which they comically over-reacted to one playoff appearance in a lockout-shortened season (and the ugly way it ended against the Bruins). Clarkson was physical and fit the Randy Carlyle mold, and had one good offensive season under his belt, so the Leafs opened the vault for him.

How it ended: Clarkson got himself suspended before he could even play a meaningful game in Toronto, then was awful when he finally did take the ice. He never fit in with the Leafs, his contract was quickly recognized as

hockey's worst, and the fans were in the process of turning on him when a

miraculous offer from the Blue Jackets sent him packing. The Leafs are still on the hook for over $20 million in cash to Nathan Horton just to make the Clarkson deal go away.

1. Pretty much everyone ever signed by the Rangers

The deal(s): I know, I know, this is cheating. But it's the only way to make this list work without it being nothing but Ranger signings. No team has been more active in free agency over the years, and no team has come anywhere close in terms of signing awful deals. Let's go through some of the history:

2002 – Darius Kasparaitis: This one is all but forgotten today because of what came after, but the veteran defenseman got a six-year deal and only managed to play one full season before eventually being sent to the minors in 2006.

2002 – Bobby Holik: The Rangers paid $45 million to land a second line center, then bought him out after two seasons.

2007 – Chris Drury and Scott Gomez: The Rangers signed both players on the same day back in 2007, giving them a combined 12 years and spending over $86 million in the process. Drury was bought out in 2011, while Gomez was traded after only two seasons.

2008 – Wade Redden: The defenseman got six years and $39 million; he lasted two years before the Rangers buried him in the AHL.

2011 – Brad Richards: This one was a nine-year deal worth $60 million that was bought out just three years in. And it doesn't even seem that bad in the grand scheme of terrible Rangers deals. That's how stiff the competition is.

Why it made sense at the time: You could excuse the Kasparaitis and Holik deals on the grounds that there was no salary cap at the time, so money didn't really matter to a wealthy team like the Rangers. Post-cap, though… well, "not learning from your mistakes" is about the best explanation that comes to mind.

How it ended: With New York being the gold standard for free agency failure. Remember, no matter what your team does on Friday, you can always comfort yourself by remembering that at least they're not the Rangers. (Note: Comfort does not apply to Rangers fans.)

Sean McIndoe has been writing about the NHL since 2008, most recently for ESPN and Grantland. He spends most of his time making jokes on twitter, where you may know him as @downgoesbrown. He appears weekly on

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