Top 15 2016 Free Agent Signings NHL Teams Are Already Regretting

Despite the fact that there hasn't been a superstar free agent in seemingly a decade, year after year, huge contracts are handed out come July 1st. With young stars often locked up on long-term deals well before they're 27, it's very rare that a big name hits the open market. It appeared we were going to get one last summer in Steven Stamkos, but after a year of speculation, he ended up re-signing with Tampa just a few days before July 1st. Once Stamkos was off the board, the free agent market dried up in a hurry and teams were essentially forced to look at aging veterans coming off a solid season. Third liners ended up getting top-six forward level contracts while some players got contracts based off of their reputation, rather than the skills they showed in 2015-16.

Often times in free agency a team is paying for a player that said player was, rather than the player they will be. That is a huge problem and why it's better to steer clear of handing out big contracts come July 1st.  We're not even a full season into these contracts but they're already looking like bad deals for the teams that signed them.

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15 Reilly Smith

Sergei Belski-USA TODAY Sports

While this wasn't a free agent acquisition this past July, the Panthers did ink Reilly Smith to a new deal in July. The Panthers acquired Reilly Smith from the Boston Bruins in 2015. After a year with the Panthers, Florida signed Reilly Smith to a brand new, 5-year, $25 million contract extension. Paying that kind of money would suggest that the Panthers expected Smith to be a top six forward, but it's pretty clear Smith will be a bottom-six forward for the duration of his contract. After 50 points last season, as well as 8 in the team's first round playoff loss, the Panthers expected Smith to take a step forward this year.

Smith's on pace for less than 40 points after 52 games this year and the Panthers have taken a step back in general. Smith's new deal with a $5 million cap hit is set to kick in next year and the Panthers can't be feeling too good about that right now.

14 P.A. Parenteau (New York Islanders)

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It turns out the Islanders were right to give P.A. Parenteau a look, as Parenteau has enjoyed a decent season in New Jersey, and is once again on pace to reach 20 goals. He's doing it on a one-year deal worth $1.25 million so it's a little curious as to why the Islanders waived him before the season started. This isn't so much as the Islanders regret signing Parenteau to a deal, but there's got to be some sort of regret for letting Parenteau go so soon. While Parenteau will never be the player he was a few years ago when he was putting up nearly 70 points a season, he still has some gas left in the tank and plays on a very team-friendly deal.

13 Danny Dekyser

Tom Szczerbowski-USA TODAY Sports

It's clear at this point that the Detroit Red Wings, for the first time in decades, have to begin rebuilding. In an effort to keep their playoff streak alive, as the team is set to move to a new arena after this season, the Wings made some bad cap moves this past offseason. They re-signed Danny Dekyser to a six-year deal worth $30 million. Perhaps it's a little unfair to pin this on Dekyser, but his plus-minus totals have dipped this season, now at minus-15 through 50-plus games. The Wings are at the bottom of the Eastern Conference, and with Dekyser entering the prime of his career, he needs to be one of their defensive stalwarts.

The Wings are committed to Dekyser but at this point, the Wings will have to make tough decisions as to who they keep after this year.

12 Troy Brouwer

Sergei Belski-USA TODAY Sports

The Calgary Flames have shown some improvement this year after a disappointing 2015-16 season. The team made it a point to bring in some veteran help and brought in Troy Brouwer, who scored some big goals for St. Louis in last year's playoff run. Perhaps we'll see more of Brower's value if the Flames make the playoffs, but so far, the move to bring in Brouwer at four years for $18 million is a little questionable. Brouwer is 31 years old and plays a hard style of hockey. It's a young man's league now, so one has to wonder if Brouwer's body will continue to hold up for 82-game seasons.

He's on roughly the same pace in point totals that he had last year, but his plus-minus numbers have dipped, as he sits as minus-11.

11 Devante Smith-Pelly

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The Devils acquired Devante Smith-Pelly from the Montreal Canadiens at last year's deadline. On an expiring contract DSP found new life in New Jersey, as he went on a tear to close out the season. Smith-Pelly scored eight goals in the Devils' final 18 games, and was rewarded with a two-year deal at $1.3 million a season. While it's not a hard contract to swallow, Smith-Pelly has been a huge disappointment this year in New Jersey, as he sits at two goals midway through the season. He's been a healthy scratch at times this season, as he's continued to struggle in finding consistency at the NHL level.

One has to wonder if DSP will again be on the trading block at this point next season. He's been traded twice in the last three seasons, and it could be three in five by 2018.

10 Loui Eriksson

John E. Sokolowski-USA TODAY Sports

The Canucks couldn't seem to decide whether they wanted to rebuild or contend. In a questionable move considering those circumstances, the Canucks handed out one of the richest contracts in free agency last summer when they signed Loui Eriksson who was coming off a 30-goal season in his final year with the Bruins. Eriksson has a six year deal worth $36 million and a full NMC for the next two years and a NTC through 2020.

The idea was that Eriksson could be a linemate of the Sedin twins, but he has already been moved off their line this year and he's nowhere close to the 30-goal pace he put up last year. The Canucks have stayed in contention, but this just seems like a move that will keep the Canucks in purgatory.

9 Matt Martin

Tom Szczerbowski-USA TODAY Sports

The Leafs have been one of the better stories this season, as the team sits in striking distance of a playoff spot after a 2015-16 season where the goal was to win the lottery and draft Auston Matthews. With some newfound cap space, something the Leafs haven't had in a while, they decided to sign fourth liner Matt Martin to a four-year deal worth $10 million. While Martin hasn't really been a hinderance to the team, was it really necessary to give Martin $2.5 million a year? The Leafs' rebuild isn't quite taking as much time as initially expected, so you have to wonder if that cap space could have been saved for a trade acquisition in a playoff push. Either way, it's not a huge mistake, but it's a little questionable.

8 Mikkel Boedker

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After their most successful season in franchise history, the Sharks probably felt they had to do something to take another step. They decided to sign Mikkel Boedker to a four-year deal worth $16 million. Boedker had been a servicable second line winger in Arizona and was traded at last year's deadline to Colorado. Boedker has yet to score 20 goals in a season in his NHL career and his numbers have dipped this season. It seems like he may even struggle to reach 10, as he has just six goals in 56 games and isn't getting the ice time he used to out in Arizona. It has to make you wonder if the Sharks should have used their resources elsewhere to address the need for speed on their team.

7 Dale Weise

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Dale Weise unexpectedly got extended ice time in Montreal for parts of last season and he enjoyed a career year at the best possible time. He scored 14 goals in 56 games with the Canadiens in 2015-16 before his play dipped off following his trade to Chicago. After failing to score a goal with the Blackhawks, Weise landed a four-year deal with the Philadelphia Flyers worth $9.4 million. Weise has since found himself as a healthy scratch for several stretches this season and doesn't seem to have that same spark he had in Montreal the last couple of years. At this point you have to wonder if Weise's career has already peaked, even though he's only 28. It's hard to see him turning things around in Philly.

6 Alexander Radulov (Only 1 Year)

Eric Bolte-USA TODAY Sports

Whoa, whoa, whoa, back off angry Habs fans. As a Montrealer myeself, I'm fully aware that Alexander Radulov has been the team's best forward this season. He has excited crowds with his ability to control the play and to set up his teammates. Marc Bergevin made arguably the best free agent signing of the summer, landing a top line winger for less than $6 million. The problem? He only signed him for one year.

While it was a calculated risk, as Radulov hadn't played in the NHL for five years, Radulov's value has skyrocketed this season and he's set to be a UFA again in July. Now over 30, Radulov will be looking to cash in and the Habs will be straped for the cap space to re-sign him for the amount he wants. It'd be devastating if the Habs lose Radulov for nothing. If he could turn back time, Bergevin would have inked Radulov to a multi-year deal.

5 James Reimer

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With Roberto Luongo getting up there in age and the Panthers looking like a team on their way, it made sense for the Panthers to look for a young goaltender to take some pressure off Luongo and perhaps take the reins as Luongo continues to slow down. In 21 starts this season, Reimer has managed a .915 SV% with a 2.55 GAA. Those numbers have gone up recently, but Reimer's bad start to this season hurt the Panthers while Luongo was recovering from offseason surgery. Reimer has been able to shoulder the load before, but you have to wonder why the Panthers committed five years to Reimer. Luongo likely has 2-3 good years left, so maybe Reimer's cap hit of $3.4 million will eventually look like a bargain.

4 David Backes 

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The Bruins may be coming alive now after having fired Claude Julien and getting a good start under Bruce Cassidy. However, with the coaching excuse out the window, it's time to start looking at the Bruins' moves under GM Don Sweeney and team president Cam Neely. Why was David Backes signed to a five year deal at age 32 worth $6 million a season? The Bruins are trying to stay in playoff contention, but it's clear this team's time to win the Stanley Cup won't come for another few years. Having an aging Backes on a $6 million cap hit will come back to haunt them when they need to acquire help on their blue line and the Bruins must be realizing that now.

3 Andrew Ladd

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Andrew Ladd was signed by the New York Islanders after the Isles let a younger Kyle Okposo walk in free agency despite having good chemistry with John Tavares. It was hoped that Ladd's playoff experience would be of use to the team, but so far, Ladd looks like a player who's really slowing down at 31. Like the Bruins, the Isles recently made a coaching change, turning to Doug Weight to replace Jack Capuano and it's sparked the team for now, as Ladd's play has gotten better as well.

Ladd got a max-term contract at seven years worth $5.5 million a season this past summer it's not looking like Ladd will be a player worth that much until he's 38. The team also has to think about keeping Tavares happy so he signs an extension. Does letting Okposo walk only to sign Ladd help their cause?

2 Milan Lucic

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The Edmonton Oilers are enjoying a successful season and seem set to return to the playoffs for the first time since 2006. While the new blood Peter Chiarelli has brought in is paying some dividends, it's already looking like giving Milan Lucic $7 million a season for the next seven years will hinder the Oilers. In his late 20s, Lucic has already slowed down considerably and will continue to do so. He has a chance to reach 20 goals this season, but we have to remember he's playing with the likes of Connor McDavid and Leon Draisaitl, who have the ability to inflate their wingers' point totals.

The Oilers could have easily saved that cap room for extending their young stars or looking for more affordable options. This contract will look worse and worse as time goes on.

1 Frans Nielsen 

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As said before, the Red Wings were looking to extend their playoff streak and in turn they gave out some expensive contracts in free agency. One of their moves was to sign Frans Nielsen away from the Islanders (another player the Isles should have kept). Nielsen is on a six-year deal worth $5.25 million a season. The Wings sit at last place in the East and it seems like Henrik Zetterberg's days in Detroit are numbered as the Red Wings are heading for a rebuild. If Zetterberg were to leave in free agency that could leave Nielsen as their no.1 center for the foreseeable future.

While Nielsen's play hasn't dipped this season, it just doesn't seem like the Wings filled a need in free agency and they're stuck on a bad contract with the 32-year-old.

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