The Detroit Red Wings were loving life before the salary cap. The team they put together for their 2002 Stanley Cup looked like a video game roster. The likes of Yzerman, Fedorov, Hull, Robataille, Lidstrom, Chelios, Hasek could never be on the same roster in today’s NHL.

But it wasn’t just Detroit enjoying this financial freedom. The much less successful teams like Toronto, Philadelphia, and New York were able to throw money around like the world was ending and if they signed a bad contract? Who cares! Just throw more money at the problem and find someone else.

By the time the salary cap hit the NHL they were the last of the big North American leagues to impose any kind of luxury tax, salary cap, or revenue-sharing; it was time for them to catch up. Although it can be painful to see your team have to sacrifice players to become cap-compliant it makes it exciting for fans to see so much player movement and balances the league with all of that talent being spread around.

Some teams will definitely throw far too much money at those former Cup-winners to try and capture some of that magic for their own roster. The prized acquisition is brought in with much hype but it seems like the more money you throw at a player, the harder it is to be satisfied. The best free-agent deals tend to be of the low-risk variety. Brad Richards to Chicago for example. In the end, players are human and unpredictable. And once they hit UFA age, it can become a total crapshoot. Contract management has now become a serious aspect of winning. Decisions are magnified, and a bad contract can kill a team’s chances at success and get many people fired.

Shockingly, many of the GMs who pulled the trigger on this list’s players retained their job, (even the guy with more than one). So click away and check out which of your favorite free-agent flops made the cut. To clarify, this list will only include guys who were signed as free agents, rather than players retained by a team via an extension. You won’t see contracts like Roberto Luongo’s or the infamous Rick DiPietro contract, as both those signings took place while still under their old contract. Entries like that belong on a list like this.

15. Cristobal Huet – 4 years, $22.4 million

UPI/Bill Greenblatt

UPI/Bill Greenblatt

After the first of their three most recent Cup wins in 2010, Chicago was in salary cap hell. One of the leading causes of that pain was Cristobal Huet’s flop of a contract. His $5 million-plus cap hit for four years would have been fine if he managed to assert himself as their franchise goaltender. But his inconsistent play in 2009-10 led to rookie Antti Niemi taking the reigns. Huet would play just one period in their Cup-winning postseason. That would be the last time Huet played in the NHL.

The Blackhawks won their three Cups with goaltenders not considered top-tier while Huet has plied his trade far away from Lord Stanley’s Cup out in Switzerland.

14. Sheldon Souray – 5 years, $27 million

via oilersnation.com

via oilersnation.com

Oilers fans might blame Jarome Iginla for Souray’s disaster turn in Edmonton. Iginla knocked Souray out of the lineup when the two had a fight just six games into Souray’s first Oiler season. Souray would perform much better the next season but Iginla struck again the following year. This time it was a hard check into the boards that left Souray concussed.

With all of these injury problems, Souray’s relationship with management deteriorated and he requested a move out of town. It got quite ugly and after he went unclaimed on the waiver wire he found himself in the minors.

Instead of showcasing his talent on a talented AHL team he instead got in a fight and injured his hand. No other team would claim such a risk on the waiver wire and Edmonton was eventually forced to buy out his last year.

And where is Souray today?

After a bounce back year with Dallas, then earning another big contract with Anaheim, Souray suffered more injuries and Ducks GM Bob Murray has said “He’s finished.”

13. Rob Blake – 2 years, $12 million

via calisportsnews.com

via calisportsnews.com

Rob Blake had a great run with his first NHL team (LA) that lasted over 10 years. However he was traded to Colorado late in 2000-01 when it was clear the Kings couldn’t afford him. It worked out great for Blake as he won his first Stanley Cup that year.

After four seasons in the Mile-High City he returned to his draft team in 2006 as a UFA. This time L.A. forked out the big bucks at $6 million per. Unfortunately his play dipped dramatically. His point totals were nearly halved and his plus-minus was awful.

Blake is still a member of the Kings organization and recently won another Stanley Cup in his first year as Assistant General Manager.

12. Jeff Finger – 4 years $14 million

via bleacherreport.net

via bleacherreport.net

Many Leaf fans responded to this signing with “Who’s Jeff Finger?”

To pay $3.5 million per year doesn’t seem like much in today’s inflated defense-market but back then it was a shocker. There may have been some competition for his services but the mutual feeling across the NHL was that Cliff Fletcher had messed up big time.

The next thing Leaf fans were saying was “The Leafs got Fingered!”

11. Mike Komisarek – 5 years, $22.5 million

DAVID COOPER/TORONTO STAR

DAVID COOPER/TORONTO STAR

Mike Komisarek was known as a professional, selfless, hard-working, physical defenceman. But in Toronto his stock dropped like a rock.

Montreal fans will tell you that Andrei Markov makes his former defensive partners rich. Sheldon Souray, Mark Streit and Komisarek have all seen their point totals inflated when playing with the talented Russian.

It’s a fairly common mistake to sign a player above their paygrade and think that automatically makes them a better or more complete player. Unfortunately for Toronto, they wouldn’t learn from this contract and have THREE entries on our list.

10. Ryan Smyth, 5 years, $31.25 million

Perry Nelson-USA TODAY Sports

Perry Nelson-USA TODAY Sports

While Oilers fans will always see Ryan Smyth as a hero, Colorado fans might want to forget Smyth’s stint as an Av. The Islanders traded for “Captain Canada” at the 2007 deadline, Smyth’s contract year, but couldn’t retain his services. That summer, Smyth signed with the Avalanche for five years and $31.25 million. Injuries limited Smyth to 55 games in his first season in Colorado. Smyth produced in Colorado, scoring 96 points in 132 games but injuries hurt his stock. That and it was just a bad fit for a Colorado team who should have been looking to rebuild. Smyth would have been better suited going to a contending team for less money. After two seasons, the Avs traded Smyth to the Kings.

9. Brad Richards – 5 years, $39 million

Adam Hunger-USA TODAY Sports

Adam Hunger-USA TODAY Sports

Brad Richards was the belle of the ball during his UFA summer of 2011. In a shallow pool he was undoubtedly the big fish. A former Stanley Cup and Conn Smythe winner, many GMs thought he would look perfect centering their top line.

Glen Sather has a history of ‘winning’ big UFA sweepstakes and this was no exception. He signed Richards to a $60 million deal over nine years. Coming off a career year and reuniting with Cup buddy Torts had Ranger fans salivating at the possibilities.

But the dream of simply purchasing your franchise center didn’t come true. Richards displayed flashes of productive top-six play but also found himself demoted to the fourth-line and even a healthy scratch in the playoffs! Age had caught up with him and his contract was bought out just three years after signing it.

Of course Richards hit the lottery again with Chicago, winning another Cup and increasing his stock all while collecting big money from the Big Apple.

8. David Clarkson – 7 years, $36 million

John E. Sokolowski-USA TODAY Sports

John E. Sokolowski-USA TODAY Sports

Every team wants a tough grinder who can score goals. And for a time David Clarkson was just that. His 30 goal season and impressive lockout year quickly elevated him to the status of sought-after UFA. Toronto ‘won’ the sweepstakes with a massive overpayment and the ballad of ‘Wendel Clarkson’ began.

He could never live up to the contract and it showed. He was trying so hard to earn his dollars that he got away from what got him the contract in the first place. For $3 million a year you love him, for $5 million, you hate him.

The hockey gods smiled on Toronto as they swapped a rich team’s problem for a poor one. Columbus had the cap room and Toronto had the cash.

This trade is one of the first strokes of good luck to happen to Toronto, and god knows they deserve it.

7. Sean Avery – 4 years, $15.5 million

via dallasnews.com

via dallasnews.com

When this big mouth was playing his rookie season in Detroit he received some much needed advice from one Brett Hull. Sean Avery had stood up on the bench to chirp Colorado’s Joe Sakic before a faceoff but Hull was having none of it. He yanked Avery down and told him “You do not get to talk to Mr. Sakic”. Their veteran-rookie relationship must have been strong as Avery would actually live with Hull and his wife in Detroit that season. It’s a shame that Hull’s wisdom couldn’t sink in.

Perhaps Hull still felt that veteran-rookie tingle when he suggested that Dallas sign him in 2008. Avery had recently come off his incident with Brodeur that resulted in the ‘Avery rule’ so his stock was at an all-time low. Most teams wanted to keep him far away from their dressing room so this deal was a huge surprise. Instead of a simple one-year audition contract they spoiled him with four years at $15.5 million. He lasted just 23 games before his ‘sloppy seconds’ comment had him suspended indefinitely.

6. Sergei Samsonov – 2 years, $7.5 million

via bleacherreport.net

via bleacherreport.net

 

While the short term of the contract made it digestible, Sergei Samsonov was just a plain disaster in Montreal. Samsonov has five 20-plus goal seasons before his Montreal arrival, so the Habs felt they were getting a legitimate top six winger. Samsonov finished his Canadiens career with nine goals and 26 points in 63 games. The Habs waived him in his first season. He would be traded to Chicago the following summer. How quickly can one give up on a free agent signing?

5. Ville Leino – 6 years, $27 million

Timothy T. Ludwig-USA TODAY Sports

Timothy T. Ludwig-USA TODAY Sports

At the time, Buffalo wanted to make a statement. They wanted to splash some money at a serious UFA to prove they were no longer restricted to a small-market budget. But after missing out on Brad Richards (another buyout) they settled on making their statement with… Ville Leino. This proved to be the wrong kind of statement as the signing was a miserable failure.

Leino was a huge risk. He had done nothing in Detroit or Philadelphia until his magical playoff run of 21 points in 19 games. He would thrive with high-end linemates and become known as a great playoff producer. Buffalo got to see this first-hand as he helped the Flyers eliminate them from the playoffs in 2011.

His time in Buffalo was brutal and culminated with zero goals in his last 58 games played.

Considering Buffalo’s current situation, I’ve seen a few Sabres fans react much more positively to Leino. His buyout didn’t count against the cap and he contributed to the downward spiral that led towards golden boy Jack Eichel.

A free agent flop that had a happy ending.

4. Tomas Kaberle – 3 years, $12.75 million

via sportsnet.ca

via sportsnet.ca

Tomas Kaberle’s weak stint in Boston should have been a warning sign that he was a declining asset. The Boston Bruins traded for the longtime Leaf defenceman for their Stanley Cup run in 2011 to bolster their power play. Kaberle not only didn’t help on special teams, but didn’t really contribute anything as the Bruins seldom used him on their road to the Stanley Cup. They let him walk in free agency only for the Carolina Hurricanes to hand him a three year, $12.75 million deal. They quickly realized their mistake and traded Kaberle after just 29 games in which Kaberle was a defensive liability and didn’t help on the power play.

Kaberle didn’t do much better in Montreal, as the Habs went through one of their worst seasons ever, finishing last in the East in 2011-12. After the 2013 lockout shortened season, the Habs bought out the last year of Kaberle’s contract. He now plays in his native Czech Republic.

3. Chris Drury – 5 years, $35.25 million

via blueshirtsbulletin.com

via blueshirtsbulletin.com

In what was perhaps Glen Sather’s worst day as a general manager, Chris Drury was one of the two bad contracts he handed out. Following an amazing run in Buffalo, the Rangers signed Drury to a five year, $35.25 million deal. Drury’s career would be derailed by injuries in New York. In his first season he scored 58 points, down from his 69 in Buffalo the year before but still a solid year. His production would dip every year from there and after a buyout for the final year of his contract, he retired at the age of 35.

2. Scott Gomez –  7 years, $51.5 million

Ed Mulholland-USA TODAY Sports

Ed Mulholland-USA TODAY Sports

This was a highly anticipated off-season with Daniel Briere, Gomez, and Drury all looking to cash in.

New York bagged two of the three in a move that surprised Sather himself. The bigger surprise was around the corner when both would flounder mightily in the Big Apple.

The truly boneheaded move was that they let Michael Nylander go to sign these two. At the time the Rangers’ top sniper was Jaromir Jagr. Jags had always struggled to find a center he liked in New York and he finally clicked with Nylander. Instead of keeping a good thing going for a much cheaper price, Sather childishly went after the shiny new toy and cast Jagr’s favorite center aside. They would try forcing chemistry but Jags ended up playing with 21-year old Brandon Dubinsky.

Gomez had one great season in New York, but after a down year in 2008-09, Sather miraculously rid himself of the disastrous contract to Montreal and landed Ryan McDonagh on top of that. Ask Habs fans how they felt about that Gomez contract. He was eventually bought out following the 2012-13 lockout.

1. Wade Redden – 6 years, $39 million

via nhlsnipers.com

via nhlsnipers.com

A New York Post writer called this one “the worst in the history of the NHL, if not in the history of hard-cap pro sports”. I would suggest he look a little further back at the contracts his own team threw at the likes of Bobby Holik, Valery Kamensky and the others on this very list. But it was definitely bad enough to make it to #2.

Redden had a tough go during the end of his Ottawa tenure. His mother was battling cancer and he faced injuries, a big contract, and declining play. He turned down a trade and it went public. He stated he wanted to win a Stanley Cup as a Senator and would even take a home-town discount, but his time in his Nation’s capital was done.

Redden admitted that the size of the contract got to him. Like many others, he got away from his game trying to live up to the over-sized salary. His play continued to decline and the rest of the league was shocked to see one of the highest-paid defencemen riding the bus in the AHL.

While it’s hard to feel sorry for millionaires it’s also a shame to see a talented player crushed with the weight of unrealistic expectations. Redden was ready to sacrifice for his team and is now remembered much differently.

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