Ah, the NHL offseason- that special time of year when big name free agents wrestle for overpriced fees and over-extended contracts. The 2015-16 offseason did not disappoint, bringing it’s share of baffling signings and puzzling trades. As the Stanley Cup champion Pittsburgh Penguins gear up for another playoff run after retaining most of its roster from last year, the rest of the NHL teams try to address their needs and desires by signing free agents, offering trades and managing cap space. What better time for a struggling GM to save face or restore the interest of a disillusioned fan base? Yes, this is that special time, when the disappointments of last season are far enough in the rear view mirror to clean the slate, when we can convince ourselves that the aging ex-superstar is just what our club needs to change things around and make a deep playoff run.

Most of the movement that we will see before the season starts is now over. Coaches will begin to strategize based on the strengths and weaknesses of their respective teams. The signing period opened up with the news of the Larsson-Hall trade and built up to the baffling trade of P.K. Subban for Shea Weber. Coveted free agents such as Okposo, Ladd, Backes, and Staal, among others, have been signed. Coaches have come and gone, and there have even been more stirrings regarding the rise of analytics and the positioning of NHL teams towards the use of the data and the opinions of analysts.

Despite the fact that the fanbases on the losing end of these moves may be still trying to come to term with the loss of key players or management, only time will tell if the money spent and contracts dished out this summer were worth the chess pieces received. Quite conveniently, all the craziest moves of the offseason are discussed right here. Let’s see which moves teams will regret once this 2016-17 ends, if not sooner.

15. David Backes – Boston Bruins

Aaron Doster-USA TODAY Sports

Aaron Doster-USA TODAY Sports

This was not an awful move at all. The Bruins lose Loui Erikkson, who has had disappointing production in the past and a large cap hit, and gain David Backes, a proven leader and goal scorer. The issue here is whether or not Backes’s potential contribution to the Bruins is worth the 5-year, $30 million contract. With Boston already having a need filled for top line centers in Bergeron and Krejci, the deal doesn’t appear to be worth the cost.

In the past season, Backes posted the most ice time in the last four seasons, yet we saw a decrease in goals, assists, and +/- ratings. While these kinds of changes are expected with age, it is safe to say they will likely continue exponentially. He will likely see less ice time in Boston, who will regret paying such a high premium for Backes in the next couple years.

14. Matt Pfeffer Firing – Montreal Canadiens

Mike Carroccetto / Yahoo! Sports Canada

Mike Carroccetto / Yahoo! Sports Canada

This one doesn’t have the spotlight that a coach or player has, but it is an interesting move to say the least. The Canadiens fired Matt Pfeffer from their analytics staff after he allegedly made a strong case against the trade of P.K. Subban for Shea Weber. In the debate of the value of hockey analytics, this is an important bet by Montreal’s management team against the use of analytics. Perhaps they felt analytics did not give enough respect to the notion of Weber’s return to Canada. Either way, it is unlikely the best and brightest minds in analytics are going to want to work with in Montreal after these rumors.

Pfeffer had this to say on his stance regarding the Subban/Weber trade: “They didn’t tell me it was over that,” Pfeffer told thn.com. “But I guess everyone knows now where I stood on the Subban-Weber trade. There are times when there’s some possibility that there would be another side to the argument, but this was one of those things where it was so, so far outside what could be considered reasonable. I made a pretty strong case, but I made the case that the analytics made. This wasn’t a personal thing.”

13. Loui Eriksson – Vancouver Canucks

Greg M. Cooper-USA TODAY Sports

Greg M. Cooper-USA TODAY Sports

Loui Eriksson will provide some much needed excitement to the Vancouver fan base, as it will be exciting to see him play with the Sedin brothers, but will likely disappoint fans a few years into the deal. We have seen Eriksson’s numbers climb during his time with the Bruins, but he may be more of a goal-scorer there then he will be playing with the high-scoring Sedin brothers. However, the centerman will be 31 by the start of the season, and it is likely that his best years are behind him. Although the Canucks’ fan base will be hoping for 30-plus goals from the versatile player this year, his more volatile years with the Stars make the case that he may not be so consistent.

The Canucks are less likely to regret the addition of Eriksson for 2016-17, but are likely to regret the term by next summer (six years, $36 million).

12. Letting Dan Humhuis Go – Vancouver Canucks

Anne-Marie Sorvin-USA TODAY Sports

Anne-Marie Sorvin-USA TODAY Sports

Though he is a little old for the league at 33, and likely will be on the decline in the next few years, Hamhuis would have been willing to stay in Vancouver for a short period and a relatively affordable rate.

The Canucks will have to adjust to losing a great defenseman who has shown strong leadership qualities. He would have been worth the price even as a third pairing defenseman. Instead, the Canucks will miss his presence on and off the ice.

The Canucks don’t seem to be in a rebuilding state of mind, as they signed Eriksson and even attempted to sign Milan Lucic. Those aren’t the actions of a team that is rebuilding. If that’s the case, then why would Jim Benning and company let a leader like Hamhuis go?

The Canucks seem to really be stuck in limbo for the next few years, unless management realizes where they stand as a franchise.

11. Erik Gudbranson – Florida Panthers

Robert Duyos-USA TODAY Sports

Robert Duyos-USA TODAY Sports

Florida traded one of their top young defenseman alongside a fifth round draft pick for a fourth round pick and forward Jared McCann. This was another trade designed to avoid a cap hit, since Ekblad remained an essential player for the Panthers to keep. The major loss to the Panthers is that they are not a team with a bank of great defensemen, so it puts pressure on developing players to step up in Florida. The team signed Keith Yandle in free agency, presumably to play alongside Aaron Ekblad, but they also lost Brian Campbell to the Chicago Blackhawks.

The move seems to put the Panthers one step forward and two steps back. The Panthers though, still don’t seem to have the blue line depth to make a deep playoff run. They’ll likely regret this move be next offseason, after a disappointing playoff exit.

10. Dale Weise – Philadelphia Flyers

Eric Bolte-USA TODAY Sports

Eric Bolte-USA TODAY Sports

The Flyers signed 27-year-old Dale Weise to a four year contract this offseason. It is not too hard to see how he would be a good fit for the Flyers. At 6-foot-2, 206 pounds, he will be a strong physical presence on the Flyers’ third or fourth line. Weise will be reliable for a steady offensive boost next year, but with a career high of 14 goals, he doesn’t appear to be worth the $2.35 million annual hit.

However, the Flyers were able to avoid making the mistake of offering an expensive contract to a declining player over 30, so even if Weise stops producing, this deal won’t hurt too much.

Still though, paying a career bottom six player coming off a career-high season going into free agency never seems to pay off. This will likely be Weise’s richest contract of his career and we have to remember, the Flyers are a team that always seem to overpay.

9. Teddy Purcell – Los Angeles Kings

Robert Mayer-USA TODAY Sports

Robert Mayer-USA TODAY Sports

The Kings gave up Milan Lucic to create cap space to make a few signings, one of them being winger Teddy Purcell. While it’s true that Lucic didn’t push the Kings into a deeper playoff run this year, signings like Teddy Purcell don’t seem to push the Kings to a better position either. He seems to provide a certain amount of off-ice value given his history with the Kings, but the lack of hope given by his age and past numbers should raise some concern about this year with the Kings.

That being said, the way he ended last season and the playoffs provided some promise, and apparently enough incentive for the Kings to make that final signing, and a short term deal at that. The Kings will hope that they can make a deep playoff run this year after a disappointing five-game series loss to the Sharks in this year’s opening round. It’s unlikely Purcell will be what puts them over the top.

8. Chris Kelly – Ottawa Senators

Winslow Townson-USA TODAY Sports

Winslow Townson-USA TODAY Sports

The Senators signed the 35-year-old Chris Kelly to a one year, $900,000 contract this offseason. Known for his leadership qualities, the contract is a bit of a gamble due to suffering a fractured femur at the beginning of the 2015-16 season. Though this a low-risk investment for the Senators, it’s hard to see it panning out especially well given the severity of his injury and his age.

The Senators are another team that doesn’t seem to quite know whether they will be contenders for the next few years or if they will have to reload. They clearly felt they could’ve done better last year, as Dave Cameron was fired and Guy Boucher was hired. Perhaps the signing of Kelly was due to the Sens seeing Kelly as a good fit in Boucher’s system.

However, as long as he stays healthy, Ottawa might get their money’s worth.

7. Brian Elliott – St. Louis Blues

Dennis Wierzbicki-USA TODAY Sports

Dennis Wierzbicki-USA TODAY Sports

The Blues paid a premium this season for the desire of their younger franchise goalie to have less competition in net. Elliott, with a record of 23-8-6 last season, could easily be seen as a starting goalie on more than a few teams in the NHL. They gave up the veteran goaltender for the 35th pick in the 2016 draft and a conditional 2018 pick.

St. Louis clears some cap space with the trade, but it still seems like a lopsided trade that the Blues will regret if Jake Allen slumps this year and Carter Hutton has trouble filling in. The Blues’ window to win a Stanley Cup is small and it got smaller this offseason after they lost veterans like David Backes and Troy Brouwer to free agency.

They’ve taken a heck of a gamble on Jake Allen, as he’s never established himself as a no.1 goaltender.

6. Trading Shaw and Teravainen – Chicago Blackhawks

Candice Ward-USA TODAY Sports

Candice Ward-USA TODAY Sports

The Blackhawks are not to be judged too harshly for their offseason moves. They had to avoid cap issues and that meant losing a few key pieces to the team, most notably in 25-year-old center Andrew Shaw. On one hand, the price Shaw was asking for would have been difficult for Chicago to manage given their current commitments. On the other, Shaw’s departure leaves slack in the offensive production that has not yet been picked up.

Both Shaw and Teravainen represent skilled young players that the Blackhawks had to let go of this summer. Hopefully, the fact that this hand felt forced to the Blackhawks management will relieve the feeling of missing Stanley Cup star Andrew Shaw.

A big reason why the Blackhawks were able to win three Stanley Cups in six seasons was due to the depth they had among their group of forwards. Their depth is now suffering, so we’ll have to see if it bites Chicago.

5. Randy Carlyle Replacing Bruce Boudreau – Anaheim Ducks

James Guillory-USA TODAY Sports

James Guillory-USA TODAY Sports

The firing of Bruce Boudreau led way to the re-signing of former Ducks coach Randy Carlyle. At the surface, this switch seems somewhat logical. They lose a winning coach and gain a wining coach who has had more playoff success with the Ducks. He was a fan and player favorite for the job after leading the Ducks to the Stanley Cup in 2007. However, a deeper look reveals the Ducks may not be better off. Puck possession in Anaheim trended downwards to 48% and 44% during his final two years in Anaheim. Carlyle posted similar numbers (under 50%) consistently during his time in Toronto as well. In his absence, the Ducks have managed to have much stronger puck possession (53%) and will likely see a drop in the standings this year if Carlyle’s pattern continues. Anything short of a run to the Stanley Cup will have the Ducks regretting this move, which makes it an extremely high risk.

4. Jared Boll – Anaheim Ducks

Aaron Doster-USA TODAY Sports

Aaron Doster-USA TODAY Sports

The signing of Jared Boll seems to support a path for the Ducks under Carlyle. Though Carlyle has been credited with desiring to adapt to the new direction of the NHL, signings such as Jared Boll affirm the Ducks are not completely ready to let go of old ways. Jared Boll is an enforcer-type player that doesn’t seem worthy of the two-year deal offered by Anaheim. He has consistently been a liability on the ice, as his former team’s 5v5 shot attempt% and 5v5 goals for% has been much better without him on the ice.

The NHL is trending in a direction where players like Boll aren’t of great value to their teams. This seems like a step in the wrong direction for the Ducks, who have built their team on skill. By this time next yeare, it’s very unlikely the Ducks will be saying the signing of Boll really helped them improve as a team.

3. Trading Taylor Hall for Adam Larsson – Edmonton Oilers

Perry Nelson-USA TODAY Sports

Perry Nelson-USA TODAY Sports

One of the first big moves of the offseason was the Oilers trading for defenseman Adam Larsson. They paid the price of one of their most promising young wingers, Taylor Hall, who was the first overall pick of the 2010 draft. Though it did fill a need at the blue line for the Oilers, a vast majority of fans were upset after hearing Hall was given up for Larsson (and nothing else).

It is possible that the Oilers see something in Larsson and feel that they have enough young offensive talent, but this was clearly a lopsided trade that the Oilers will regret as they watch Hall mature in New Jersey.

It’s hard to believe the Oilers couldn’t have gotten more for someone like Taylor Hall, who has shown the ability to be a point-a-game player when healthy. The move made it feel like they rushed into a trade without getting the best possible value for him.

2. Andrew Ladd – New York Islanders

Dennis Wierzbicki-USA TODAY Sports

Dennis Wierzbicki-USA TODAY Sports

Ladd is an exciting addition to the Islanders roster, but at age 30, the seven-year, $38.5 million contract is likely one that the Islanders will regret by next offseason, if not slightly later. On the bright side of the deal, Ladd is by no means a slumping player, managing to score more goals with significantly less ice time than in the 2014-15 season. He currently plays at around 50% in the possession game, however his GF% is too low to expect Ladd to be a contributor worth a seven season commitment. While it does work to fill the hole left by Kyle Okposo and Frans Nielson for the time being, this move is undoubtedly a step down.

The Islanders will have to make some headway to a Stanley Cup in the next two years for this move to be worth it, but it’s very unlikely the addition of Ladd puts them over teams like the Penguins and the Lightning.

1. Trading P.K. Subban – Montreal Canadiens

Eric Bolte-USA TODAY Sports

Eric Bolte-USA TODAY Sports

The biggest headlines this offseason revolved around the trade of P.K. Subban for Shea Weber. Canadiens fans were shocked to see their best defender traded away for a veteran player. While Subban and Weber are both top defenders, Subban is three years younger and statistically, a better defender.

The trade would like be easier for Montreal’s followers to stomach if a high draft pick or additional player was provided. However, the deal went through and it is pretty safe to say that Subban’s numbers will make the Canadiens regret the trade, if they don’t already.

This trade is said to make the Canadiens a better team for the next couple of years, but that ultimately, Nashville will have won the trade when all is said and done. If the Habs don’t make a serious run at the Stanley Cup soon, this can go down as one of the worst trades in their franchise’s history.

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