Top 15 Recent NHL Free Agent Signings Teams Are Already Regretting

The summer can be hard for NHL fans. Endless months of no hockey, no hockey news, no awesome highlights from around the league, no fantasy. It can be a dull affair. The most exciting news to bless us from the hockey world from time to time in the summer months are free agent signings; who’s going where and for how much, but most importantly, will it work out? There are always signings to talk about, and of course it’s fun to speculate on whether or not this player can make it with their new team. This past season has been no different, with many star players packing their bags and joining new teams for their next adventure.

This list looks to explore the failed additions, or more specifically, the one that teams will come to regret, or in some cases, already deeply regret. Some people saw these coming from a mile away. When declining players or career bottom six forwards start to get paid like All-Stars, you can already tell the signing will be a bust. Well, these 15 have already shown to be that and we're not even at the halfway point of the season yet.

Needless to say, the Islanders are mentioned quite a bit in this list considering their offseason madness. Their start this season has shown how bad their moves were.

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15 Frans Nielsen – Detroit Red Wings

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Another long-time Islander that didn’t re-sign with the Isles this year, Frans Nielsen instead opted to give the Detroit Red Wings a shot. The Islanders originally selected the Swede 87th overall in the 2002 draft. After 10 years with New York, Nielsen signed a six-year deal that will make him a Detroit Red Wing through the 2021-22 season. Although Nielsen can definitely play a top-six role, having him there for the next six years seems counter-productive.

Nielsen has always been solid, but has never broken the 60-point mark, and is more likely to get you around the 40-point mark than the 50 mark, which is fine of course. But with an aging core, and just having lost Pavel Datsyuk, I think the Red Wings are going to regret having signed Nielsen and would have been better suited spending more money for a better forward.

14 Jordin Tootoo – Chicago Blackhawks

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Everyone remember Jordin Tootoo? Selected way back in 2001, 98th overall by the Nashville Predators, Tootoo is the first person of Inuit descent to play in the NHL, wearing the number 22, obviously a play on the pronunciation of his name. He spent the last two years of his career with the New Jersey Devils, where he wasn’t particularly productive, although he never really has been.

Tootoo’s move to Chicago makes sense in a way; the Blackhawks like signing older, character players to add to the team flair, and Tootoo definitely fits the bill. At 33 years old, he’s definitely near the end of his career. He only signed a one-year deal with the Hawks, and although it’s hard to truly regret one-year deals, I think they would’ve let this one go if they can go back a few months.

13 Shawn Matthias – Winnipeg Jets

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At just 28 years old, Matthias is well into the season with his fifth NHL team, the Winnipeg Jets. He was drafted originally by the Detroit Red Wings, 47th overall, back in 2006. Matthias quickly made it clear that he would make a fine third or fourth line winger, and provide excellent depth to any team, but he would never be quite good enough to crack the top two lines on a regular basis. His point tally in his career thus far prove as much; since he started in the NHL, his highest point tally was just 27 (last year he was limited to 11 points with the Avalanche).

After his contract ended with Colorado, Matthias opted for Winnipeg on a two-year deal. So far this year, the forward has just two goals to show for it. How about that Patrik Laine, though?

12 Joe Colborne – Colorado Avalanche

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Colborne was selected 16th overall in the first round by the Bruins, although he never played with the team and was then eventually traded to the Maple Leafs in 2011. After almost three years there, he joined the Calgary Flames in 2013 after being traded, and this is where he found some success in the NHL, playing three full seasons with the Flames. His most successful campaign was last year when he earned 19 goals and 44 points. After his contract expired, it wasn’t likely that the Flames would re-sign him, so Colborne opted for Denver, where he signed a two-year, $5 million deal.

In 21 games this year, the 26-year-old center has only three goals and one assist and is on pace for much lower totals than what he earned with the Flames last year. In terms of his offensive contribution, I’m sure the Avalanche will have some regrets there.

11 David Schlemko – San Jose Sharks

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Schlemko is an NHL defenseman who originally went undrafted, but was signed as a free agent by the Coyotes in 2007. Since then, the stay-at-home defenseman has played for the Dallas Stars, Calgary Flames, and New Jersey Devils, before signing long-term with the San Jose Sharks. As you can see, Schlemko bounced around for quite a while and signed with a fourth different organization when he joined the Devils. In 67 games, he put up his best numbers yet, netting six times and earning 19 points.

A small sample size of success to be sure, but not for the Sharks who jumped on the defenseman and signed him long-term to a four-year deal. He has no goals and just five assists with the team so far, but I’m not too sure the success he found in Jersey will be mirrored in San Jose.

10 David Perron – St. Louis Blues

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David Perron signed a two-year deal in the offseason with the team that had originally drafted him 26th overall back in 2007, the St. Louis Blues. Perron made the rounds since then, being traded first to the Oilers, then to the Penguins, and then to the Ducks, before ultimately ending up back with the Blues. Perron struggled to find success last season in Pittsburgh, which is why he was ultimately traded to Anaheim for Carl Hagelin, who was wonderful for the Pens during their cup run. David Perron, not so much.

So far, Perron has seven goals in 25 games, putting him on pace for just over 20 goals. Perron, however, lacks consistency and I personally don’t see him breaking 20 goals this season. However, on a Blues team that has no lack of scoring, it shouldn’t be too much of an issue for St. Louis.

9 James Reimer – Florida Panthers

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Everyone remember Reimer? He was the Leafs goaltender that burst onto the scene in 2010 and made himself a niche in Toronto, often fighting for the first goalie position with Jonathan Bernier. But when Babcock came in, after one year something was clear; neither of these goalies were good enough in his opinion to be the main netminder. What does that mean? Well, they were both promptly excused from Toronto.

Reimer was first traded to the San Jose Sharks before the 2016 trade deadline, finishing the season with the Sharks. As a free agent for the first time in his young career, Reimer signed a five-year contract with the Florida Panthers, as official backup goaltender for the Florida Panthers. It hasn’t been the ideal start for Reimer. He has a .896 save percentage, and just three wins in nine games played this season. If the Panthers thought that maybe Reimer would take over one day, it’s not looking that good so far.

8 Matt Martin – Toronto Maple Leafs

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What used to be the heart and soul of the New York Islanders, Martin was originally selected 148th overall in the 2008 NHL Entry draft by the Islanders, until he signed this offseason to a four-year, $10 million contract with the Toronto Maple Leafs. Last year with the Islanders, Martin's fourth line with Casey Cizikas and Cal Clutterbuck was considered to be the best fourth line in hockey by most of the NHL, so it seems surprising to me that the Islanders wouldn’t want to re-sign him for a small price.

Instead, he opted for the Maple Leafs, and it hasn’t quite been the best start. After going a large portion of the season with getting his first goal, Martin now only has two goals in 24 games for the Leafs, but more worrying is the fact that the electricity he brought for the Islanders hasn’t quite been the same for the Leafs.

7 Dan Hamhuis – Dallas Stars

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Dan Hamhuis is an NHL veteran, being the second defenseman overall to be selected after Mike Komisarek in the 2001 NHL draft. He was originally selected by the Nashville Predators, although in 2010 he joined the Vancouver Canucks on a six-year deal. Hamhuis found some success with the Canucks, although his last two seasons were peppered by many long-term injuries. In the summer offseason, the Canucks opted to end their relationship with Hamhuis, who instead signed a two-year, $7.5 million deal with the Dallas Stars.

In 24 games with the Stars, Hamhuis has yet to find the back of the net but has earned a meager five assists with his new team. The Stars have also had a hard time defending this year, with the Stars having one of the worst goal differentials in the NHL. At 33 years old, Hamhuis is certainly looking at the bottom half of his career.

6 Lee Stempniak – Carolina Hurricanes

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At 33 years old, Lee Stempniak signed this offseason with his tenth NHL team, the Carolina Hurricanes. Originally drafted in 2003 by the St. Louis Blues, Stempniak never stayed in one place too long, unable to build himself a niche in any team. He’s never been a very productive forward, barely cracking the top six, depending on the team of course. Last year with the New Jersey Devils was one of his most productive with 41 points, prompting the Hurricanes to jump the gun and sign the winger to a two-year contract.

With four goals in 25 games thus far, Stempniak definitely has not met expectations. On a Hurricanes team without much offensive punch, Stempniak was expected to have a larger offensive role for the Canes, although he looks set to hover around the 40-point mark once again.

5 Dale Weise – Philadelphia Flyers

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I have a personal soft spot for Dale Weise, and of course feel bad including him on a list like this. But I do think the Flyers are/will regret signing a player like Weise, and here’s why. Weise was originally introduced to NHL hockey when he was drafted 111th overall by the New York Rangers. He was later traded to the Canucks and then to the Canadiens, and that’s where things got interesting. Fans in Montreal fell in love with Weise’s heart and passion, and of course his effort on the ice, but most importantly his love of the Canadiens. That particular fire elevated his game in Montreal to a level I doubt we’ll see again while he’s a Flyer.

After scoring 14 goals in 56 games with the Canadiens last year and even occasionally playing on the top line, Weise’s production seriously halted when he was traded to the Chicago Blackhawks, who were adding depth up front for a cup run. In 25 games with the Flyers this year, Weise has just two goals.

4 P.A. Parenteau – New York Islanders

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P.A. Parenteau is another questionable free agent that the Islanders decided to sign in the offseason. Instead of trying to hold on to their quality forwards, they basically went out shopping for an entirely new team to surround captain John Tavares, and so far the experiment has not gone as planned. You know how I know they regret signing a washed up player like P.A. Parenteau to a one-year contract? Because they put him on waivers before the season even started. He would be claimed by the New Jersey Devils, his official new team.

Parenteau had already played two seasons with the Islanders between 2010-12, earning 53 points and 67 points consecutively. Obviously, those productive years were long gone for Parenteau, who had only 41 points in his previous campaign with the Leafs.

3 Mikkel Boedker – San Jose Sharks

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This one here has to be one of the worst free agent signings in this year’s offseason. The 26-year-old Mikkel Boedker is a Danish hockey player who was selected eighth overall by the Coyotes and spent his entire career there before being traded to the Avalanche last year before the trade deadline. However, the two were unable to come to a contract agreement and Mikkel Boedker signed a four-year, $16 million contract with last year’s finalists, the San Jose Sharks.

He’s had perhaps one of the saddest starts to this year’s campaign, with just two goals and two assists in 25 games thus far. Their big offseason acquisition really isn’t looking too good for the Sharks with Boedker unable to find his game whatsoever so far.

2 Loui Eriksson – Vancouver Canucks

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The Vancouver Canucks were not destined for great things this season, and so far, they’ve proven everyone right. Signing Loui Eriksson was a confusing move, to say the least. After a solid 63 points in Boston the year before, the Vancouver Canucks took this as a sign that he deserved a six-year, $36 million deal. In his first game with the Canucks, he scored his first goal – impressive, but unfortunately, it was in his own net when the goalie was out due to an oncoming penalty.

With 11 points in 25 games so far, Loui is on pace for less than 40 points this season, a solid downgrade to the success he had last season. I’ve had a feeling that Eriksson might be on the decline, ever since he joined the Bruins from the Stars, and I don’t think he’ll find much success on a Vancouver team with no identity that also has a lack of scoring.

1 Andrew Ladd – New York Islanders

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Andrew Ladd was with the Winnipeg Jets for the majority of the 2015-16 season before being traded to the Chicago Blackhawks, who were adding some serious star power to their line-up for what was supposed to be a very deep Stanley Cup run. Obviously, that didn’t work out, as the San Jose Sharks found themselves in the finals against the Pittsburgh Penguins. Chicago, therefore, started getting rid of their rentals, Andrew Ladd perhaps being the most important of all.

The Islanders were going through some changes of their own. Kyle Okposo, perhaps their second best forward after John Tavares, signed with the Sabres. Frans Nielsen left as well, signing long-term with the Detroit Red Wings. As you can see, the Islanders were desperate for a top-six forward. In comes Andrew Ladd. The Islanders quickly signed him to a seven-year, $38.5 million contract that hasn’t started off so well for the winger. Ladd has had a horrible quarter-season so far, and despite the small sample, I’m sure the Islanders are a little anxious for Ladd to start producing.

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