Top 15 Worst NHL Signings And Who Would Have Been A Better Option

With the 2016-17 NHL season starting to wind down, more and more eyes are starting to look to the upcoming free agent pool. The NHL offseason is a very fundamental part of the game and it's a time that can literally make or break hockey clubs.

Every hockey team's desires are different and most needs can be met with a free agent signing - it's essentially an extended Black Friday. Much like customers on Black Friday, NHL teams often fight over players and often times it simply comes down to who can wave the biggest salary around. With that being said, the introduction of the salary cap has certainly changed things - I mean, no longer can a team sign both Teemu Selanne and Paul Kariya in the same offseason (Colorado in 2003).

At the end of this season, some very notable names will be in the free agency pool and teams will be ready to pounce. Many teams will be looking to add a star player to their roster and hopefully create a cup-contending team, but some will also be looking for a strong centerpiece to build around for the future.

For many NHL fans and GMs alike, free agent signings can be very exciting and in many circumstances, a beacon of hope. However, free agent signings can also leave many people scratching their heads in confusion or even boiling with frustration.

In this list we will be looking at 15 of the worst NHL signings and pointing out some better options the respective GM could have gone with. Please keep in mind that these are in no particular order.

With all that out of the way, let's get into it!

15 Toronto Maple Leafs Sign David Clarkson

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Better Option: Viktor Stalberg

The 2013-14 Toronto Maple Leafs had a pretty decent roster and when the free agents became available, Toronto went a bit crazy in hopes of making a cup-contending roster. The Leafs would end up signing David Clarkson to a whopping seven year, $5.25 million per year cap hit. The Leafs certainly had high hopes for the one-time 30 goal scorer and needed him to be a strong second line winger behind Phil Kessel. Unfortunately, the 30 goal season was a bit of an anomaly for Clarkson and his production in Toronto was nothing short of awful.

The Leafs needed a second line point producer and Clarkson only managed to record 15 goals and 26 points over 118 games while bringing an ugly -25 to the table. A much better choice would have been Viktor Stalberg who was signed by the Nashville Predators for a four year, $3 million per year contract. Granted, Stalberg didn't have an amazing stint with the Predators, but he did manage more points than Clarkson in far fewer games and was drastically cheaper. Stalberg is a very offensively gifted player and with Nashville being as defensive-minded as they were, he just wasn't a good fit there.

14 Sean Avery

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Better Option: Matt Cooke

Prior to the 2008-09 season, the Dallas Stars made a terrible decision in signing the infamous Sean Avery. Coming off one of his best professional seasons (33 points in 57 games), the Stars' brass deciding to take a chance on the edgy Sean Avery - he was signed to a generous, borderline insane four-year, $15.5 million contract. Unsurprisingly, Avery didn't mesh with the Stars and lasted a mere 23 games before getting canned - in fact, he was largely disliked by most of his teammates and deemed unwelcome.

I get what the stars were going for - they were hoping to add some edge to a pretty decent looking hockey club and make a playoff run. A much better alternative would have been another infamously edgy player, Matt Cooke who was signed to a two-year, $2.4 million contract by the Pittsburgh Penguins. Cooke would go on to put up 61 points in 155 games while sporting a +19 rating and he even raised the cup with the Penguins - he would later be resigned by the Penguins for another three prosperous seasons.

13 Ville Leino


Better Option: Tomas Fleischmann

Coming into the 2011-12 season, the Buffalo Sabres were among the cellar-dwellers of the league and in desperate need of change. With a lot of cap room and desperation sinking in, the Sabres decided to go big and offer the Finnish-born, Ville Leino to a handsome six-year, $27 million contract ($4.5 million per year). Prior to the 2011-12 season, Leino was coming off his career-best season with 53 points in 81 games but unfortunately, could not carry on his productivity with the Sabres.

Leino would only play 137 games over three years with the Sabres where he tallied only 10 goals and 46 points - talk about disappointing. Signing a very similar, four-year and $18 million contract ($4.5 million per year) that year was Tomas Fleischmann who was much more productive with the Florida Panthers. Fleischmann actually played out his entire contract and recorded 145 points in 262 games which included a 27-goal season in 2011-12. With a better contract, better productivity and being younger, Fleischmann would have been a way better signing.

12 Colorado Avalanche Sign Teemu Selanne

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Better Option: Sergei Fedorov

Being the NHL legend that he was, how could you blame the Colorado Avalanche for taking an expensive $5.8 million, one-year shot on Teemu Selanne. Coming off of a 28 goal, 64 point season with the San Jose Sharks one would have expected similar production in the 2003-04 season with the 'Aves'. Unfortunately, that season was a complete anomaly for Selanne that saw to him notching a meager 32 points and even playing a decent amount of fourth line minutes.

The free agency pool was ridiculously stacked for the 2003-04 season and there were a handful of talented alternatives for Selanne. One possibility could have been another NHL legend, Sergei Fedorov - one of the best Russians to ever play the game. Fedorov signed a five-year, $26.24 million ($5.25 million per year) with the Anaheim Ducks and put up 31 goals and 65 points in his first season. He would only play five games in the next season before being moved to the Columbus Blue Jackets. The Avalanche could have taken Fedorov instead of Selanne for a similar contract and received double the offensive production.

11 Montreal Canadiens Sign Sergei Samsonov

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Better Option: Brendan Shanahan

As I've touched on a previous article, Sergei Samsonov was a notoriously horrendous signing by the Montreal Canadiens. The 'Habs' had very high hopes for the four-time 20+ goal scorer, Samsonov and signed him to a lucrative two-year, $6.25 million contract. Samsonov only ended up playing one season of his contract where he contributed nine goals and 26 points while being healthy scratched a handful of times.

The 2006-07 free agency was another star-studded one with numerous other players that would have been better than Samsonov. A perfect example was NHL legend, Brendan Shanahan - even at the end of his career, 'Shanny' was still good for around 50 points per season. Shanahan played his final two full seasons (he played a half-season to finish his career) with the New York Rangers and earned $6.5 million over those two seasons - an income very comparable to Samsonov's contract. In that 2006-07 season, 'Shanny' notched 29 goals and 62 points in 67 games - over double Samsonov's numbers.

10 Columbus Blue Jackets Sign Nathan Horton

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Better Option: Jarome Iginla

Nathan Horton, the poor guy, was an absolute Band-Aid during his NHL career - he has been held back by countless injuries ranging from back issues to severe concussions. Horton was, and technically still is a great hockey player who is capable of 50 points per season when he's healthy. I just can't understand why the Columbus Blue Jackets decided to sign such an injury-prone player to such a massive seven-year, $37.1 million contract - a contract he has only played 36 games over one season of.

There were countless suitable alternatives in the 2013/14 free agent pool but I think Jarome Iginla would have been the best. Yes, he is eight years older than Horton but he is also really consistent, constantly healthy, and very productive. Iginla signed a one-year, $1.8 million contract with the Boston Bruins and racked up 30 goals and 61 points in that 2013-14 season. Following that season, Iginla signed a three-year, $16 million contract with the Aves where he has continued his productivity. In hindsight, it's easy to say that the Blue Jackets could have signed 'Iggy' to a large contract and received so much more in terms of production, leadership, and consistency.

9 New York Rangers Sign Bobby Holik

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Better Option(s): Martin Gelinas & Curtis Joseph

Bobby Holik was a massive centreman standing at 6'4" and 230 lbs and the contract the New York Rangers signed him to was equally as large - prior to the 2002-03 season, Holik was signed to a five-year, $45 million contract. He was a good hockey player, don't get me wrong, but if you're paying upwards of $9 million per year for about 45 points per season, you may have made a mistake. The Rangers thankfully realized their blunder and bought out Holik at the conclusion of the 2003/04 season.

Looking at the Rangers' roster for that season, you could argue that they didn't need anybody at all - especially down the middle behind Mark Messier and Eric Lindros. Their biggest weaknesses (if any) were down the left side and in between the pipes. The Rangers could have picked up a very affordable Martin Gelinas (three-year, $4.85 million) who had a very similar point production as Holik. On top of Gelinas, the Rangers could have signed an elite NHL goalie such as Curtis Joseph (three-year, $24 million) who had far better numbers than the Rangers' netminders, Mike Dunham and Dan Blackburn.

8 New York Rangers Sign Scott Gomez

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Better Option: Pavel Datsyuk

A name I've covered in a previous article of mine, Scott Gomez is either a name you love or a name you just can't stand. Gomez was a very good hockey player capable of 60 points per season, but was also known to be quite inconsistent. In 2007, the New York Rangers signed the Alaska product to a generous seven-year, $51.5 million contract. Gomez did put up pretty good numbers with the Rangers but was ultimately overpaid and New York wisely shipped him off  to Montreal in return for their current captain, Ryan McDonagh.

The 2007 free agents list was riddled with superstar UFAs including the magician, Pavel Datsyuk. Would you believe that Datsyuk was signed for less money than Gomez? Well, he was and for seven years as well ($46.9 million). Did I mention that in the first two years of that contract he notched back-to-back 97 point seasons? Looking back, I'm sure the Rangers wished they offered Datsyuk a similar seven-year contract for upwards of $55-60 million. Oh well.

7 Detroit Red Wings Sign Uwe Krupp

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Better Option: Jyrki Lumme

Uwe Krupp was a reliable, 12-season NHL veteran going into the 1998-99 free agency and was definitely on many team's radars. The big 6'6", 240 lbs German was locked down by Detroit for a four-year, $16.4 million contract and had the Detroit faithful very pleased with how their defensive core was looking. Unfortunately, injuries dragged Krupp down into the depths of the NHL and he only ended up playing 30 games for the 'Motor city' where he managed a miniscule six points.

There were many suitable replacements for Krupp in the '98 free agency pool but I'd look no further than Jyrki Lumme. Playing only one season less than Krupp coming into the '98 season, Lumme was also a very reliable and seasoned NHL D-man. Lumme was generally good for around 30 points per season and was a cool +76 during his long career. Playoff experienced, reliable and productive, Jyrki Lumme was definitely a better option.

6 Detroit Red Wings Sign Stephen Weiss

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Better Option: Mike Fisher

Stephen Weiss played 11 seasons with the Florida Panthers and really proved himself as a great two-way centreman capable of around 50 points per season. The Detroit Red Wings saw Weiss' potential and signed him to a five-year, $24.5 million contract. For whatever reason, Weiss just couldn't maintain his level of play and would only go on to play in 78 games over two seasons - he contributed a disappointing 29 points. He has not played in the NHL since his last season as a Red Wing.

There were a handful of available, quality NHL centremen in that 2013/14 playoff pool but only one in particular seemed to pop out at me - Mike Fisher. The current Nashville Predators captain was signed by the 'Preds' for a two-year, $8.4 million contract - $700 thousand cheaper per season than Weiss. He's not amazing by any means, but Fisher is a an above-average player who is easily capable of notching upwards of 35-40 points per season. Mike Fisher, in hindsight was definitely a better alternative.

5 Toronto Maple Leafs Sign Jeff Finger

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Better Option: Ron Hainsey

Jeff Finger played 199 games over his short four-season NHL career and put up some decent numbers for a D-man - unfortunately, his defensive game was not so decent. After just 94 games with the Colorado Avalanche, the Toronto Maple Leafs decided to take a shot on Finger with a healthy looking four-year, $14 million contract - a gamble to say the least. After 105 games, the Leafs' realized their mistake of an investment as Finger's defensive game left him as a -18 (over two seasons) and a constant healthy scratch in the 2009-10 season - he was sent down to the Toronto Marlies where he played two seasons before calling it quits.

The Leafs were looking for a solid two-way D-man to slot in on their second pairing and based on Finger's numbers in Colorado, it was a fair chance to take - however, he was offered just way too much money. A better alternative would have been Ron Hainsey who signed a five-year, $22.5 million contract with the Atlanta Thrashers. Hainsey is a solid blue-liner who's adequate in the defensive end, good for around 20-30 points per season, and a great leader. Hainsey would have been perfect for the Leafs on their second pairing and a much, much better investment.

4 New York Rangers Sign Wade Redden

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Better Option(s): James Wisniewski & Craig Conroy

Wade Redden was a great NHL D-man during his first 11 seasons with the Ottawa Senators so it made sense for the New York Rangers to offer Redden a big six-year, $39 million contract. Redden went from being good for about 40 points per season with the 'Sens' down to 25 points per season, then down to 15 and then he was gone. Just two seasons into his contract the once elite defenceman lost his roster spot with the Rangers and never recovered - he went on to play just 29 more NHL games for two different teams (Blues & Bruins) before hanging up the skates in 2013.

The 2008-09 Rangers had a lot of depth throughout their roster but were a bit lacking down the middle and slightly on defence. With the cap they spent on Redden, the Rangers could have picked up two players - centreman, Craig Conroy and defenceman, James Wisniewski. Conroy was signed by the Calgary Flames for two years at $2.1 million and put up very respectable numbers while providing stability down the middle. Wisniewski easily could have been signed for four years and $3-4 million - he contributed 25-50 points per season from 2008-2012.

3 Carolina Hurricanes Sign Alexander Semin

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Better Option: Zach Parise

Alexander Semin is an incredibly talented Russian hockey player who tore up the NHL during his seven-season ride with the Washington Capitals - he was arguably one of the best wingers in the league. Semin quickly became a very expensive asset and once his contract expired with the 'Caps', he was signed by the Carolina Hurricanes for a gigantic one-year, $7 million contract. He marked up a mediocre 44 points in that 2012-13 season (career low since his rookie season) and for some reason was resigned by the 'Canes' for another big contract - five years at $35 million. His point production and motivation just kept going downhill and he was bought out following the 2014-15 season.

Also signing a big contract in 2012 was fellow left-winger, Zach Parise who was signed by the Minnesota Wild for a make-you-look-twice, 13-year, $98 million contract - $538 thousand more of a cap hit per year than Semin. Parise is currently a staple in the dominant Minnesota Wild's offensive core and produces around 50-60 points per year while being a leader and wearing the 'A'. It's easy to see just how much more valuable Parise would have been to the struggling, but up-and-coming, 'Canes' roster.

2 Boston Bruins Sign Martin Lapointe

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Better Option: Alexander Mogilny

Martin Lapointe was an average second line winger, but a great third line addition - the Boston Bruins simply just expected too much of the French-Canadian. Coming off of career-best season of 57 points with the Detroit Red Wings, the Bruins decided to take a four-year shot on Martin Lapointe (#20) in 2001 that saw to him earing over $5 million per season. Lapointe was a good player but put up only 83 points over three seasons - hardly worthy of that kind of cash.

In that same 2001 offseason, NHL legend Alexander Mogilny was signed to a four-year, $22 million contract with the Toronto Maple Leafs - he earned only $500 thousand more than Lapointe over the next three seasons. Mogilny would contribute 166 points in those three seasons - funnily enough, exactly double Lapointe's production. The Bruins had a very impressive roster and could have slotted Mogilny alongside Joe Thornton and the aforementioned Sergei Samsonov on their first line.

1 Philadelphia Flyers Sign Ilya Bryzgalov

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Better Option: Brian Elliott

Ilya Bryzgalov was a very good goaltender whose only fear was "bear in forest" - a good quality to have when you have over 100 mph slap shots flying at your head. Coming off of four impressive seasons with the Phoenix Coyotes (only dropping below a .920 SV% once), the Philadelphia Flyers invested heavily in 'Bryz' with a nine-year, $51 million contract. Unfortunately, he couldn't maintain his stellar level of play and had two of his worst professional seasons (2011-2013) with 'Philly' before being shipped off to Edmonton.

With the young and rising Sergei Bobrovsky in the backup position, the Flyers were looking for a solid number one to take most of the starts between the pipes. A better option would have been Brian Elliott who signed with the St. Louis Blues for one season and $600 thousand - he resigned the following season for a two-year, $3.6 million contract. From 2011-2013, 'Moose' would put up an impressive combined .933 SV%, 3.84 GAA, and 12 shutouts. Can't blame the Flyers for taking the shot on Bryzgalov, but Elliott would have been a much better investment.

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