They say hindsight is 20/20 and boy are we going to dive in to some hindsight today. Every year each team makes many moves to “improve” their club. Some work out great and others not so much. This list is dedicated to those that fall in to the not so much category. Every type of roster move makes an appearance on this list. We have Free agent signings that have gone bust, Draft picks that never panned out, resigning of a team’s own players that proved costly and of course horrific trades that blew up in a franchise’s face.
Dynasties are made based on solid decision making and the general ,anagers that feature in these moves clearly have a lot left to learn. You will see some team’s feature more that once in more than one category of move. So let’s get this started as we take a look at 20 NHL roster moves that looked terrible from the start. To keep the list recent, we're sticking with roster moves of the past five years, around the time the NHL had their last lockout. So those looking for the greatest hits of days gone past will have to look out for future articles by the great team here at Th Sportster!
20 The New Jersey Devils Acquire Taylor Hall
This is a trade that has great potential to be off this list in the near future. Taylor Hall is a super talented winger with the ability to change a game in an instant. He hasn't shown any of this ability with the New Jersey Devils. In his first year with the Devils, Hall saw a 12 point drop in production, to make it worse the loss of Adam Larsson made the team much more porous in its defensive end.
The Devils struggled to score, or keep the puck out of their own net. The Oilers prospered with Larsson, but Taylor Hall will need to return to his point per game ability for this trade not to be considered a huge mistake by the Devils.
19 The Edmonton Oilers Sign Milan Lucic
Of all the signings on this list, this one has the best potential to find its way off future lists. The Edmonton Oilers organization knew they had to get bigger and threw a pile of money at UFA Milan Lucic. The hope was that Lucic would play with McDavid and put up big points. Seems that Patrick Maroon was a much better fit for McDavid’s wing at a fraction of the cost. Lucic also had his worst statistical season playing 5 on 5 of his career. Lucic can easily turn it around but for now he ranks as one of the worst roster decisions of the last five years. With McDavid and Draisaitl set to get paid big bucks for the long haul, Lucic's contract will be a hinderance to the Oilers unless they can find a way to dump it.
18 The Edmonton Oilers Acquire Griffin Reinhart
Since taking over as General Manager of the Edmonton Oilers Peter Chiarelli has made very few mistakes. Acquiring Griffin Reinhart was definitely a mistake. 2015 was known as one of the deepest drafts in recent history. The Oilers moved the #16 and #33 picks to the New York Islanders for Griffin. For a mid-first and an early 2nd pick all the Oilers got was a defenseman who couldn't crack the lineup.
After being left exposed, the Vegas Golden Knights claimed Griffin Reinhart so now the Oilers have nothing to show for this deal. Despite being on an expansion team, Reinhart hasn't even been able to crack the starting lineup there, so it's curious to see what the Oilers possibly saw in Reinhart. This move will look even worse in the future if Matthew Barzal becomes a star.
17 Detroit Red Wings Sign Frans Nielsen
The Detroit Red Wings did make one big free agent signing in 2016, and it definitely blew up in their face. The Wings signed Frans Nielsen to a six year deal worth $31.5 million. Nielsen rewarded the Detroit Red Wings with a poor performance. Frans Nielsen scored just 17 goals and added 24 assists in 79 games. The Red Wings had brought Nielsen in to replace the production lost when Pavel Datsyuk retired. It is safe to say he struggled to fill those shoes. The Red Wings will be paying him $5.25 million a season for the next 5 years and if he doesn’t improve greatly this move will haunt the Red Wings as it gets harder and harder to sign their young players.
16 The Tampa Bay Lightning Sign Ryan Callahan
Ryan Callahan is not a horrible player by any stretch of the imagination. He was the centerpiece in the deal that Tampa received after trading their star Martin St. Louis. The reason why Callahan makes an appearance on this list is strictly due to how much he makes. After acquiring Callahan, Tampa Bay signed Callahan to a six year deal worth $5.8 million a season. Even when healthy Callahan has not proven to be worth anywhere near that. He had a career high 54 points during the 2014-15 NHL season but it has been all downhill from there. Injuries and ineffectiveness make sure Callahan has a place on this list. The Lightning would like to upgrade their blue line and add some depth on the bottom six, but Callahan's contract makes it difficult.
15 The Bruins Sign David Backes
The Boston Bruins took a big swing in free agency last year signing David Backes to a 6 year deal worth $30 million. David Backes did not live up to that contract thus far. He struggled to only 17 goals and 21 assists. This was his lowest point production since his sophomore season in the NHL. This was not what Boston expected when they signed Backes. He seemed like a completely different player with the Bruins than he was with the Blues. He was slower, his hits were down and he couldn't mesh with the Bruins team. He still has a long time on this contract to turn things around and the Bruins better hope last season was a blip and not what Backes has left in the tank.
14 The Detroit Red Wings Extend Danny Dekeyser
Not every mistake a team makes with its roster is a trade or free agent signing. Sometimes it’s making a mistake with one of its own players. The Detroit Red Wings experienced this recently with the contract extension of Danny Dekeyser. Danny Dekeyser had shown a lot of promise on the back end for the Red Wings. Detroit locked him up to a 6 year contract worth $5 million a year. Dekeyser felt the pressure of this contract and had one of the worst seasons on his career. Last season he had 4 goals and 8 assists in 82 games and suffered the worst plus/minus of his career with a minus 22. He has the potential to bounce back but right now this looks like a horrible move.
13 The Islanders Sign Andrew Ladd
Last season Andrew Ladd was the big free agent signing for the New York Islanders. They lost Kyle Okposo to the Buffalo Sabres and brought in Ladd to try and mitigate the damage. It's easy to say it was an unmitigated disaster. Ladd struggled to gain any chemistry with New York Islanders star John Tavares. Ladd scored 23 goals last season but added only 8 assists. The Islanders signed Ladd to a seven year deal worth $38.5 million. Now the Islanders are struggling to try and get Tavares signed to a longterm extension and it is failed moves like this that must make Tavares question staying with the club. He had a lot more chemistry with Okposo and the Isles could have easily used the money they spent to get Ladd and given Okposo what he wanted.
12 The Bruins Sign Matt Beleskey
I think it is safe to say the Boston Bruins panicked a little bit with this move here. The team knew they had to inject some fresh blood in to a line up that was getting a little stale and complacent. Enter in UFA Matt Beleskey, Beleskey had his breakout year with the Anaheim Ducks during the 2014-15 NHL season with 22 goals. It seemed Boston was blinded to the fact Beleskey only had 35 goals in the 5 SEASONS prior. Beleskey has been nothing but a disappointment with the Bruins. Injury trouble and ineffectiveness has limited his production. Last season he had 8 points in 49 games that is not what the Bruins expected when they signed him to help replace Milan Lucic.
11 The Ducks Trade Patrick Maroon
This trade has come back to bite the Ducks in the butt big time. In fact, it could only get worse as the Oilers start to surpass the Pacific Division powerhouse Ducks. On February 29th, 2016 the Ducks traded Patrick Maroon to the Edmonton Oilers for a 4th round pick and failed prospect Martin Gernat. Maroon had a career year last year, scoring 27 goals in 81 games gaining chemistry with Connor McDavid. What makes the trade worse, the Ducks will be giving the Oilers $500,000 a year to have Maroon. With McDavid now signed on a longterm contract, Maroon has a spot on a generational player's wing, while the Ducks could have paired Maroon with Getzlaf and Perry for the foreseeable future.
10 The Panthers Sign Dave Bolland
There is nothing good to say about this deal at all. Bolland was never a player that was worth the contract he was given by the Florida Panthers. When your career high is 47 points there is no way you should get a 5 year deal worth $27.5 million. Yet that is exactly what the Panthers did in 2014. It predictably blew up in the Panthers' faces. Bolland struggled to only 23 points in his first year as a Panther and was even worse the next season. Bolland was so bad that the Panthers had to throw in a prospect just to get a cap floor team to take him. Safe to say the Panthers are regretting this one.
9 The Canadiens Trade P.K Subban
P.K Subban has established himself as a premier defenseman in the NHL. Not only that, but he has become a public relations dream as there are few players more charitable than Subban. Subban apparently clashed with the players in the locker room back in Montreal and with the GM and coach.
The Habs moved Subban to the Nashville Predators for Shea Weber. Weber is a great defenseman but he is older and plays a much more physical style than Subban, one that isn't as conducive to today's NHL as Subban's game is. The Preds' trip to the Stanley Cup Final last year while the Habs quickly bowed out of the first round served as a bad sign for the Habs. The Habs were supposed to benefit in the short-term, but the Preds seem to be winning that side of the trade as well. As the years go by, Subban will still be in his prime, while age is bound to slow Weber down when he reaches his mid 30s.
8 The Blue Jackets Sign Nathan Horton
This had the potential to be a great signing for the Blue Jackets. Nathan Horton had been a reliable two way player. He suffered a brutal concussion during the 2011 Stanley Cup Finals and it is safe to say he wasn’t the same player after that. He signed with the Blue Jackets in 2013, yet just one year later was diagnosed with a degenerative back injury that ended his career.
He has since been moved to the Leafs for fellow list mate David Clarkson. The Jackets traded Horton away because they figured if they were going to have a bad contract on the books, it might as well be for an active player.
Who knows how Horton would have done if his body didn’t break down.
7 The Capitals Trade Filip Forsberg
This is a roster move that is going to torture the Washington Capitals for many more years. The Capitals were looking to make a deep run in the 2013 NHL playoffs. They made the grave error of trading their #11 overall pick in the 2012 NHL draft Filip Forsberg to the Nashville Predators for Martin Erat. Erat was a bust with the Capitals. He lasted 2 seasons, playing 66 games but only scored 2 goals. To make it even worse, The Capitals were eliminated in round 1 that year.
Filip Forsberg on the other hand has become a go to scorer for the Nashville Predators. Forsberg has had over 30 goals in the last 2 seasons, and added 16 points in the Predators run to the Stanley Cup Finals last season. Filip Forsberg has a long career ahead of him and he is well on his way to establishing himself as a premier player in the league.
6 The Flyers Trade Sergei Bobrovsky
It seems like the Philadelphia Flyers have been looking for a goalie since Ron Hextall retired. Little did they know they had a future 2 time Vezina Trophy winner in their grasps and they let him go for almost nothing. The Flyers traded Bobrovsky to the Columbus Blue Jackets during the 2012 NHL draft. In exchange they got a 2nd round pick and a 4th round pick in 2012 and a 3rd round pick in 2013. Bobrovsky has gone on to stardom with the Blue Jackets and is the reigning Vezina winner.
The Flyers used one of the picks on Anthony Stolarz who shows potential as a future starting goalie. Too bad they gave up on the elite one they already had.
5 The L.A Kings Extend Dustin Brown
There is no doubt that Dustin Brown played an important part in the L.A Kings two Stanley Cup wins in 2012 and 2014. IN between those 2 Cup wins, the Kings signed Brown to a 8 year deal worth $47 million ($5.875/season) The contract made no sense as he was already showing signs of a decline. Since the contract has been signed, the Kings find themselves in cap hell and Brown has found himself stripped as a captain. With no one to take on his contract, and a buyout that would strangle the team for years it seems like Brown and the Kings are stuck together. It seemed like Brown's game went down the drain as soon as he signed the deal, meaning this was probably very poor timing for the Kings to lock him up.
4 The Edmonton Oilers Draft Nail Yakupov
Leading in to the 2012 NHL Draft season all anyone could talk about was the plan to fail for Nail. Nail Yakupov was seen as the next in a long line of Great Russian players. He was thought to have great speed and a wicked shot but he definitely failed to achieve much success in the NHL. The Edmonton Oilers selected Nail Yakupov 1st overall. His rookie year was solid, leading all rookies with 17 goals. But that season was also a shortened 48-game schedule. Once the rigors of an 82-game season reared their ugly head, Yakupov's game has disappeared.
He has scored less goals than the season before in every successive year. He is now on a last chance deal with the Colorado Avalanche. After only 9 points last season, not much is expected from him.
3 The Canucks Sign Loui Eriksson
This should have been a deal that worked wonders for everyone. The Sedins and Loui Eriksson had a history of great success during Olympic and the World Hockey Championships. They had built chemistry, yet with the Canucks none of that materialized. The Canucks paid Loui Eriksson $6 million a year and he rewarded them with the worst season of his career since his debut. Eriksson scored only 11 goals and 13 assists in 65 games. The deal has quickly blown up for the team. There is a lot of money tied up in their Swedish trio and it’s not working out. The Canucks are quickly falling into irrelevancy and it is deals like this that have buried them.
2 The Boston Bruins Trade Tyler Seguin
This trade definitely hurt the Boston Bruins. Tyler Seguin gained a reputation as a partier while with the Bruins. He didn’t fit the mold that the team wanted so they traded him. The Bruins packaged Tyler Seguin, forward Rich Peverley and defenseman Ryan Button to the Stars for forward Loui Eriksson and three prospects (Joseph Morrow, Reilly Smith and Matt Fraser).
It is safe to say he was worth much more than that. Just four years later and the Bruins have nothing to show for it. Seguin however has become a big star in the NHL, never scoring less than 70 points in a season. The Bruins still have a talented group of forwards, but just imagine what they could have had, if they had been a little more patient with Seguin maturing.
1 The Leafs Sign David Clarkson
This is a cautionary tale for NHL teams to follow. Don't go all in on a player after just one good season. During the 2011-12 season Clarkson exploded for 30 goals in 80 games. His previous career high was 17, and he would never even reach that again. The Toronto Maple Leafs would sign Clarkson to a 7 year deal worth $36.75 million. He would contribute 26 points over 2 injury filled seasons before he was traded for a player who medically was unable to ever play again (Nathan Horton)
Now Clarkson is in the same boat, unable to play and his contract belongs to the Vegas Golden Knights.
The Leafs seem to have learned their lesson, as they have spent the last few years building around their young stars and relying on draft picks to acquire talent.