NHL free agency is an interesting time of the year in which general managers spend copious amounts of cash and coin. Some of the long-term investments brokered in July pan out, and others become an instant punchline for critics, bloggers and those who have an interest in "cost certainty."
With the big day set to commence on Friday, here is a look at each team's worst moments during free agency.
Giguere wasn't the same after signing his extension.
Although J.S. Giguere was a key cog during the Anaheim Ducks' Stanley Cup run in 2006-07, he didn't perform well after being signed to a four-year extension during the summer of 2007. Of the three years Giguere remained in Anaheim, he only had one winning season before being shipped to the Toronto Maple Leafs.
Lapointe didn't have a ton of success with the Bruins.
The Bruins thought they were getting a solid player when they signed Lapointe in the summer of 2001. After coming off of a 57-point season with the Detroit Red Wings, expectations were high, but Lapointe never lived up to them during his time in Beantown.
Lapointe signed a four-year deal worth over $5 million a season, but he never lived up to the contract.
Lapointe only contributed an aggregate of 83 points during his three years with Bruins, a far cry from what was expected of him.
Leino's contract is horrendous.
Ville Leino got paid after having a good regular season and good playoff run with the Philadelphia Flyers. The Buffalo Sabres probably could have signed him for way less, and his contract is certainly one of the worst of all time.
Leino's cap hit of $4,500,000 was way too much for a player whose career high in points was 53.
Bouwmeester wasn't a great fit for the Flames.
This is another bad contract that was handed out to a good player on a bad team. With the Florida Panthers, Jay Bouwmeester was a stud on the blue line. However, once he moved up north, his game took a huge nosedive.
Bouwmeester's production dropped marginally as a member of the Calgary Flames, and he was eventually traded to the St. Louis Blues.
With the Panthers Bouwmeester put up between 30 and 40 points a year, and that number dipped into the 20s with the Flames.
Ruutu doesn't have the greatest of contracts.
Tuomo Ruutu is a talented player, but his contract is one of the worst that Jim Rutherford has ever handed out. For starters, Ruutu makes almost $5 million a year to be a top-nine player. The Hurricanes' top six is pretty set after last year's acquisitions, and Ruutu no longer is a great fit.
He is also getting older, and players usually don't have more success in their 30s than they had in their 20s.
The deal is costly and long, and it is a deal that may warrant a compliance buyout next season.
Huet won a cup with the Blackhawks as a backup.
Cristobal Huet was an average goalie with a bad contract. He was nothing special with the Montreal Canadiens. The Chicago Blackhawks took a chance on him during the 2008-09 season, and he was decent.
He then lost the starting job during the Blackhawks' Cup-winning season and was subsequently loaned to a European club. Huet made a ton of money not to play for the Blackhawks, and it was one of the rare times the Blackhawks made a bad move during free agency.
The cap hit of $5,625,000 was a burden for a while, but it didn't impact the Blackhawks' ability to remain competitive.
Smyth's tenure in Colorado could have been a lot better.
It is hard to picture Ryan Smyth as anything other than an Edmonton Oiler, but he did wear other NHL jerseys during his career. One of his most expensive sweaters was worn with the Avalanche, and it was a deal that didn't pan out.
At a cap hit of $6.25 million a year, Smyth was being paid to be an elite scorer, but he only averaged 0.72 points per game during his stretch in Colorado.
James Wisniewski hasn't panned out with the Blue Jackets.
James Wisniewski is a good offensive defender, but $5.5 million a year is a bit steep. The Blue Jackets' blueliner currently has three years left on his deal, and the first two years have been underwhelming.
It hasn't helped that Wisniewski has been hurt for stretches of his first two seasons, but thus far, the free-agent signing has been a flop.
Avery had many rea$ons to $mile.
Sean Avery didn't last long with the Dallas Stars, and the team was saddled with a portion of the contract after he was claimed on re-entry waivers.
Avery was an agitator with a big mouth, and his infamous sloppy seconds comment ended his tenure with the Stars. It is hard to believe that Sean Avery was paid just under $4 million to be a pest, but the Stars made it a possibility.
Krupp cashed in with Detroit.
Uwe Krupp will forever be known for two things, and both are directly linked. Krupp scored the Stanley Cup-winning goal for the Colorado Avalanche in triple overtime, and he cashed in during free agency with the Detroit Red Wings.
Krupp was a glue guy who fit in the bottom pairing, but he should have never made $4 million a year. While Krupp would be a solid third pairing guy during the Red Wings' Stanley Cup win in 2002, he didn't earn his full paycheck with the Wings.
Souray's game declined very quickly with the Oilers.
Outside of a 53-point campaign, Sheldon Souray's time in Edmonton was a colossal bust. The Oilers' blueliner inked a five-year deal worth $27 million, but he never truly lived up to the contract. He would later be banished to the AHL, but he eventually made his return to the NHL in 2011.
Souray's game fell off so quickly, and the Oilers were lucky that it was legal to bury contracts at that point in time.
Upshall had potential, but injuries have hurt him in Florida.
Scottie Upshall was one of the many players the Florida Panthers signed during a building period, and he was one of the few players who didn't pan out. Upshall was signed to a contract worth $14 million over four years, and to date he hasn't lived up to it.
In 53 games over two seasons, Upshall has only contributed 10 points because of injuries. If Upshall doesn't bounce back, he may be a compliance buyout candidate in 2014-15.
Blake didn't produce well at the end of his career.
Rob Blake had an amazing career with the Colorado Avalanche and the Los Angeles Kings, but his second stint in Hollywood was a bit of a bust.
It made sense that Blake was awarded a contract with an average annual value (AAV) of $6 million, but his production was less than optimal.
Between 2006 and 2008, Blake had a subpar plus-minus rating of minus-45, and he only mustered up 65 points.
Havlat was underwhelming with the Wild.
The Minnesota Wild have had a few snipers on their squad throughout their history, and Martin Havlat was one of the most disappointing. Havlat was a solid secondary scorer with the Chicago Blackhawks, but things never clicked with the Wild.
The Wild got less-than-elite production from Havlat at a 0.70 point-per-game rate, and he was eventually flipped for Dany Heatley.
Samsonov was a great fit in Montreal.
Scott Gomez's contract was terrible, but he was a trade acquisition by the Montreal Canadiens. The Habs have a historic organization, and Sergei Samsonov's free-agent deal is certainly one of the worst in league history.
Samsonov was a solid two-way scorer, and a two-year deal worth $7.05 million seemed fair. However, after only 63 games and 26 points, the struggling two-way forward was waived, and his career with the Le Bleu-Blanc-Rouge was over.
Gaustad was overpaid.
Paul Gaustad was acquired during his final year with the Buffalo Sabres, and he subsequently was re-signed. The deal Gaustad inked was for $13 million over four years, and it was a sizable overpayment for a fourth-line center.
Gaustad is great at faceoffs, he can fight and kill penalties, but $3.5 million a season is a figure reserved for second-line players.
The New Jersey Devils signed Anton Volchenkov to a contract worth $4.25 million a season, and it's a deal that hasn't worked out. The Devils thought they were getting a consistent two-way defender with a propensity to hit, but they acquired a defender with bad mobility.
Volchenkov also has not remained healthy, and it makes the contract look even worse than it is. The Devils could have spent this money in better ways, and if he doesn't improve, he could be a buyout candidate.
Alexei Yashin hasn't played in the NHL since 2006, and he is still counting against the New York Islanders' salary cap. That is how terrible his contract extension was.
Yashin's total deal was worth $71,597,944, and the Islanders were forced to carry a portion of the contract for eight years until it was completely paid off.
Richards' contract now looks like a huge blunder.
Brad Richards' contract is terrible. Due to cap recapture penalties, the Rangers will likely buy him out next summer. His deal was structured to dilute his cap hit, and in the end, it will be even worse than Wade Redden and Scott Gomez's contracts.
Richards' $6.6 million cap hit is manageable, but he currently has seven years left on his contract. The new CBA targeted legal circumventing contracts like Richards', and in the end this will have been a bad deal.
Kovy was a bust in Ottawa.
AK 27 was a very solid sniper during his prime. He was a stealthy skater with an amazing shot, and he thrived with numerous teams. The Senators thought they were getting an accomplished scorer in Kovalev, but his overall deal was a complete bust.
Prior to his arrival in Ottawa, Kovalev had put an 84-point season and a 65-point season together for the Habs. With the Senators this production took a major hit, and his best season was a 49-point campaign during his inauguarl season with the Sens.
This contract needs no explanation, so enjoy this video. In all seriousness, it is never a great idea to sign a goaltender to a nine-year contract. Bryzgalov's contract was worth $51 million, and the Flyers buyout out the final seven years of the deal as soon as the buyout window opened.
He never actualized the success he had with the Phoenix Coyotes, and he was never a good fit with the Philadelphia press.
Hull's tenure in Coyote was expensive.
The Golden Brett was one of the greatest goal scorers in NHL history, but his tenure with the Phoenix Coyotes was a huge joke.
Hull signed a two-year deal but only played five games. Hull made a whopping $4.5 million to participate in five games, and people wonder why the Coyotes have money problems.
Ziggy Palffy was a skilled scorer with the Los Angeles Kings, but he was a mega bust with the Pittsburgh Penguins. When Palffy was signed to a three-year deal, it is fair to say team brass expected him to appear in more than 42 games.
Palffy's career was derailed by a injury, but the Penguins should have done their due diligence by signing him to a shorter deal.
It is never wise to sign old goaltenders to deals longer than one year, because they aren't very durable as they get older. Hrudey was signed in the late 1990s to a two-year deal, and during his tenure in the black and teal, Hrudey won 20 games.
This was a deal that really backfired on San Jose, and it was a precusor of bad goaltending contracts to come..
Jay McKee was a defensive player who signed a mega deal to help improve the St. Louis Blues. He made $4 million a year but only played in parts of three seasons with the Blues.
McKee was signed to be a rock and anchor for the Blues, but his lack of health derailed those plans. The contract was costly for the Blues, and it was a shame because of McKee's talent.
Malone's game takes a toll on him.
With the Pittsburgh Penguins, Ryan Malone was a solid power forward who could provide some offense. The Tampa Bay Lightning thought they would get the same, but injuries ultimately impacted Malone's game.
However, the Lightning should have insured their potential risk by signing Malone to a shorter deal. Seven years is a long time for a rugged player, and there is a reason why the Lightning are trying to move him.
Connolly didn't pan out for the Leafs.
Tim Connolly was the Toronto Maple Leafs' backup plan for not signing Brad Richards, and it was a move that backfired in a huge way. Connolly collected $4.75 million a season, despite spending the 2012-13 season with the Toronto Marlies.
He is a free agent this summer, and he is bound to take a pay cut. Connolly had registered a 65-point season with the Buffalo Sabres, but he never came close to that during his time with the Leafs.
Messier wasn't a great Canuck.
The Vancouver Canucks thought they were making the right move by acquiring an elite center with multiple Cup rings, but they didn't get vintage Mark Messier. Instead, they got a player past his prime who didn't quite live up to the hype.
At age 37, you can't blame Messier for taking a huge payday, but the Canucks should have known better. For $18 million over three seasons, the Canucks got a player that averaged less than a point per game, and tons of negative press.
Nylander didn't help the Caps.
Michael Nylander is a very rich man because of Jaromir Jagr, and the Washington Capitals found that out the hard way. With Jagr and Martin Straka, Nylander centered a "Czech Connection" that was very dominant for the New York Rangers.
The trio of Czechs had great production in New York, with Nylander stringing together two seasons in which he had 79 points or more.
The Caps thought they were getting an above-average playmaker in Nylander, but he only tallied 50 points during his tenure in D.C.
Holik made a lot of money during his NHL career.
The Winnipeg Jets/Atlanta Thrashers' worst free-agent signing of all time was Bobby Holik. The ironic thing about this signing is that it came on the heels of Holik's buyout from the Rangers. Holik cashed in during free agency, and it was a deal the Rangers couldn't live with.
Holik signed a three-year deal just under $13 million, and he tallied a whopping 96 points over three seasons.