Even with a hard salary cap in place, it hasn’t stopped NHL teams from spending profligately, and stupidly.

A look at the most recent cap space projections by our friends at Cap Friendly sees nearly half the teams in a cap crunch position. That is, having around $2 million or less in cap space going into the 2018 trade deadline and free agency thereafter.

One of them is the New York Islanders, who have a major decision to make on soon-to-be free agent John Tavares (he was not extended at the time of this writing).

On some occasions since the implementation of the cap after the ’04-05 lockout, teams have found good matches that that have helped them on a deep run throughout the season and playoffs.

In most instances, though, horrendous contracts are given out to players who look good on paper but turn out to be mediocre at best, guys whose value plummets as soon as the ink dries.

Now, not all bad contracts are solely handed out during free agency (as you will see) and with players the teams acquire at the deadline who aren’t rentals, but this is usually the time of year where a GM will feel the pressure to make a move and bolster their roster, which can lead to the exact opposite.

With the 2018 trade deadline looming and free agency not long in the offing, let’s have a look at the top 20 worst NHL contracts handed out since 2005.

20. Dion Phaneuf – Ottawa Senators

The Ottawa Senators are fairly horrible in 2017-18 and part of the reason for that is the play of a diminishing asset like 32-year-old defenceman Dion Phaneuf. Once at best a 3-4 D-man in Toronto, he was signed to top two money in the middle of the 2013-14 season. It was a pretty hefty deal (seven years, $49 million; ninth highest among rearguards) for a guy who was years removed from being a Norris Trophy candidate in Calgary and whose leadership (remember salute-gate) was questionable. Phaneuf’s stats declined after signing the pact, to the point he went from a +3 in 13-14, to -11 in 10 fewer games in 2014-15. However, Leafs management pulled off the purge of the decade by shipping Phaneuf to Ottawa during a 2016 trade deadline blockbuster. His goodbye cost the Leafs nearly $5 million against the cap that season, but his $7 million cap hit, which is highest on the team, doesn’t expire until 2021.

THE CANADIAN PRESS/Adrian Wyld

19. Marc Staal – New York Rangers

As of 2017-18, the Rangers are in a good cap situation with few fat contracts impeding growth and Rick Nash’s $7.8 million coming off the books (second highest salary on the team). Yet, there is one deal they may want a do-over on and that one belongs to veteran defenceman Marc Staal. A dependable two-way defenceman who isn’t a big scorer, the 31-year-old signed a lucrative six-year, $34.2 million contract with the Blueshirts in 2015-16. Now a third-pair defenceman, he soaks up $5.7 million of New York cap space and has seen his average ice time decrease over a minute and a half since 2015-16 (19:41 to 18:07). It’s a pretty hefty chunk of change to give a guy who doesn’t play on the powerplay and whose numbers have slowly ebbed from 20 points in 2014-15 to 15, 10 and a projected 10 this season.

(AP Photo/Julie Jacobson)

18. Loui Eriksson – Vancouver Canucks

The Canucks will be in the advantageous position of having the Sedin twins current $7 million cap hits off their ledger come July 1, but the taste from underachieving winger Loui Eriksson’s six-year, $36 million pact won’t be washed away soon. Signed in free agent on July 1, 2016, it was hoped that the Swedish sniper would score 25-30 goals like he did five times previously with Dallas and Boston. It was also believed that his sound two-way skills would help calm their top two lines. Well, Eriksson scored but 11 goals in 2016-17 and finished with 24 points and a -9 in 65 games. A stark contrast from his 2015-16 campaign with the Bruins, where he had 30 goals, 63 points and a +13. So far in 2017-18 Eriksson, who mans the right wing on the Sedin’s line, has 16 points in 33 games and is -3. He also has a full no-movement clause this year, which then becomes a no trade for two seasons and then a modified no-trade the last two years of the deal.

THE CANADIAN PRESS/Jonathan Hayward

17. Karl Alzner – Montreal Canadiens

Alzner, like Marc Staal in New York, has been a fairly dependable two-way defenceman who did the little things right with Washington. He was durable, playing every game for the Capitals from 2010-11 until 2016-17 and was a decent shot blocker and hitter. After yet another 82-game season, with 13 points, and a +23 with Washington, the Habs inked the 29-year-old B.C. native to a fairly significant five-year, $23.125 million contract ($4.625 million cap hit, annually) with a modified no-trade clause thrown in for good measure. Montreal has not been good in 2017-18 and while all the blame can’t be laid at the feet of Alzner, he has been a minus player and below average on possession numbers (PDO and Corsi). Unless the team, and Alzner, see a big uptick, that near $5 million cap hit will be an albatross in no time.

(AP Photo/Mark J. Terrill)

16. Frans Nielsen – Detroit Red Wings

Red Wings’ GM Ken Holland is widely considered a genius in hockey circles. Lately, though, we think he’s lost a bit of his touch. We could have picked several terrible Red Wings’ contracts negotiated by Holland, including those of Justin Abdelkader, Danny DeKeyser, Darren Helm and Jonathan Ericsson. But for shear spur-of-the-moment lunacy we picked the big-time six-year, $31.5 million contract — with a no movement clause — Holland put in front of two-way playmaker Frans Nielsen in 2016. It seemed like a good idea at the time, as he had scored 52 points in 81 games and was a +1, along with being over 50 percent efficient on the face-off dot. But, Nielsen was already 32 then and in the season and a half since he joined the Wings, it has showed. He had 41 points and was -19 in 79 games last year and has followed it up with 15 points (30 point projection) and a -7 this season, not to mention he is the third line center playing less than 16 minutes per game.

(AP Photo/Paul Sancya)

15. Zach Parise – Minnesota Wild

Minnesota Wild GM Chuck Fletcher, much like his famous dad, “Trader” Cliff, isn’t afraid of making deals to improve his club’s chances. In 2012, Chuck took aim at key free agents Zach Parise (who is a Minnesota native and a sniper in New Jersey) and star defenceman Ryan Suter, who was with Nashville. He gave them both 13-year, $98 million no-movement contracts with an eye to them being team cornerstones for many years. Thus far, Suter hasn’t disappointed, putting up consistent offensive numbers while missing just five games in six seasons since. Parise, on the other hand, is a year older at 33 and is becoming an expensive liability. He hasn’t been near as durable as Suter, missing 48 games in his first five seasons in Minnesota and has played but seven of Minnesota’s first 46 games in 2017-18. He had back surgery in October, 2017 and saw his first game action on Jan. 2. He had one assist and was -4 playing on the second line. To boot, his production went from 62 points (+21) in 2014-15, to 53 in 2015-16 and 42 in 2016-17 (second worst output, ever).

(AP Photo/Hannah Foslien)

14. Mike Richards – Los Angeles Kings

The Flyers did the deed and the L.A. Kings are still suffering the fallout. In December 2007, the Flyers, undaunted by a little thing called the salary cap, signed Richards to a rich 12-year contract worth $69 million. After all he was their future captain and like “goalie of the future” Ilya Bryzgalov, wanted him around for a while.  Soon, though, he and a few others, including teammate Jeff Carter, were accused of being boozy nighthawks, which didn’t sit well with Richards. Flyers management must have believed the press and shipped him out just and a half years after the contract award. The Kings, who gave up Brayden Schenn and Wayne Simmonds in the deal, must not have been reading Philly newspapers then. Richards, not a great skater to begin with, skated even slower in L.A. and his production tailed alarmingly. His best season, 2008-09 with the Flyers, he had 80 points, and his first season in La-la land he had just 44. By 2014-15, he was was down to 16 points in 53 games and plodding along at -10. A drug bust and suspension followed, as did a buyout. The Kings are still pay Richards a quarter million a year until 2031-32 as per the buyout agreement.

(AP Photo/Chris Szagola, File)

(AP Photo/Chris Szagola, File)

13. Brooks Orpik – Washington Capitals

On paper, the five-year, $27.5 million deal the Caps threw at Brooks Orpik on July 1, 2014 seemed like the right thing to do at the time.  But for a guy who was soon to be 34 and had  just 13 points and a minus-3 rating in 72 games (he missed some time due concussion, which never helps), it was a little sketchy. Yes, he brings grit (he’s been suspended a couple of times for questionable hits) and experience, but he’s being paid top two money (tied for 18th overall in average defenceman salary) to play on the bottom pair in D.C. Orpik, who is now 37, is coming off a bounceback season of sorts in 2016-17, with 14 points and a +32 in 79 games. The fact, though, that they had to part with promising rearguard Nate Schmidt at the expansion draft, while still having to pay Orpik $5.5 million until 2019 has to chafe management.

(AP Photo/John Locher)

12. Brent Seabrook – Chicago Blackhawks

Seabrook has been a good old warrior for the Blackhawks since joining the club in 2005. He’s been a steadying influence on a team that has won three Stanley Cups and undergone major personnel shake-ups after said titles. The ironman has missed only 14 games in the past 12 seasons and does all of the little things correctly. Problem now is, the Hawks aren’t quite as good as they have been in the past and the 32-year-old Seabrook just signed a big, eight-year, $55 million contract that kicked in for the 2016-17 season. The pact, which carries a $6.875 million cap hit until 2024, when Seabrook will be 39, also has a no movement clause until 2022, when it becomes modified for the last two seasons. For now, Seabrook is earning his keep. The Hawks last won a Cup in 2015 and aren’t a contender this year. Signing Seabrook for big bucks — instead of maximizing his value in trade to re-tool — might not have been the best thing.

(AP Photo/Chris O’Meara)

11. Jeff Finger – Toronto Maple Leafs

This was one of the most puzzling UFA signings in free agency history. Toronto gave 28-year old defenseman Jeff Finger, who at the time had played all of 94 NHL games and recorded 24 points, $3.5m per year on a four-year deal in the summer of 2008. It was widely pointed at as the reason former genius GM Cliff Fletcher’s legacy was tarnished measurably. Not surprisingly, Finger flamed out and was a regular healthy scratch by the mid-point of the second year of the contract. He was put on waivers in 2010 and once cleared (he had a no trade clause to top it all off), he never played in another NHL game again, finishing with a total 57 career points in the NHL. Thanks to the Maple Leafs however, Finger likely has a pretty comfortable retirement fund.

THE CANADIAN PRESS/Nathan Denette

THE CANADIAN PRESS/Nathan Denette

10. David Clarkson – Vegas Golden Knights

Dave Nonis must have been drinking Brian Burke’s “Truculence Kool-Aid” when, as one of his first duties as Toronto Maple Leafs GM, signed gritty local boy David Clarkson to an eye-popping seven-year, $36.75 million deal in the summer of 2013. The then 29-year-old had one 30-goal season in the NHL with Jersey (2011-12) and was thought to be a premier “power forward” in the game. Well, in year one of his deal Clarkson gifted the city he was born in by playing 60 games and recording a grand total of 5 goals and 11 points. Another moribund 58 games followed in 2014-15 where he scored 10 goals and added five assists, while making first line money. It was an act of sheer genius that Nonis was able to send the now permanently injured Clarkson to Columbus (while bringing Nathan Horton’s dead contract back) before he got the heave-ho in April of 2015. The Golden Knights, who are really good this season, had to eat his contract, which has a $5.25 million cap hit until 2020, in order to select Columbus forward William Karlsson in the expansion draft. The silver lining? Karlsson has a career high 23 goals with Vegas and the 2017-18 season is only half over.

(AP Photo/Ross D. Franklin)

9. Marian Gaborik – Los Angeles Kings

It was a tough choice between former Stanley Cup heroes Dustin Brown (who is now 33) and Marian Gaborik (35), but in the end we went with the old guy. While Brown carries a cap hit of $5.875 million until 2022, he’s enjoyed a renaissance of sorts and could conceivably eclipse the career best 60 points he tallied in 2007-08. Gaborik, who was huge in the Kings last Stanley Cup run in 2014 when he had 14 goals in 26 games, has missed huge chunks of time to injuries since and really hasn’t been a boon to the team’s offence since. His production dipped to a career low 21 points last year, along with a -4 in 56 games. This season, the Czech veteran, who will be 36 in February, didn’t see game action until late November and tallied 13 points in 24 games as of Jan. 15, 2018. The Kings, flush with pride at winning another title in 2014, signed the Cup catalyst to a seven-year, $34.125 million contract soon after and it won’t expire until 2021, when Gaborik will be 39. However, he doesn’t have any clause precluding trades, so there is that.

(AP Photo/Chris Carlson)

8. Troy Brouwer – Calgary Flames

In terms of Calgary player personnel finances, veteran Troy Brouwer is making first line money to play on the second line but is producing like a fourth liner. The well-traveled winger was a free agent coming off a pretty decent season in St. Louis in 2016 when the Flames braintrust dangled a four-year, $18 million contract in front of him. Brouwer signed and then had his worst full season yet, statistically, with 25 point and an uncharacteristic -11 in 74 games. It hasn’t gotten much better in the second year of the pact, as Brouwer has chuffed along with just three goals and 12 points in 45 games. At that rate, the third highest paid forward on the Flames will post 22 points, another new career low. Making matters worse is the no trade clause he negotiated, with a modified one replacing it next season.

THE CANADIAN PRESS/Jeff McIntosh

7. Brandon Dubinsky – Columbus Blue Jackets

The Columbus Blue Jackets were able to shed themselves of David Clarkson’s dead contract last year — it did cost them William Karlsson — and we have to wonder if the wheels are spinning on Brandon Dubinsky, too. He’s been out since mid-December of 2017 with a facial fracture and before being injured had a measly 12 points in 31 games. Dubinsky is a great face-off man and all, however, he is 31 and even if he had seen action in all 46 Blue Jackets games this season (up until Jan. 15), he would have likely had 18 points. That kind of production would put him tied for seventh in team scoring, while he is being paid the kind of money, $5.85 million until 2021, reserved for top shelf scorers.

(AP Photo/Paul Vernon)

6. Roberto Luongo – Florida Panthers

Bobby Lu hasn’t played since the first week in December, which can’t make his team, fantasy owners or real owners all that happy. The 38-year-old netminder has an old guy injury — groin — and has played but 15 contests in 2017-18. One has to wonder whether he is starting material anymore, considering his declining stats the last three seasons and the lack of post-season berths (just one) since the Cats brought Luongo on board at the 2014 trade deadline. They assumed his $4.533 million cap hit contract that he signed with Vancouver, which doesn’t run out until 2022 and has cap recapture with penalties if he retires, since it was front loaded. Luongo, now in his second stint with Florida, also has a modified no trade clause, which, combined with his age and diminishing skills, makes him doubly difficult to deal.

(AP Photo/Bill Kostroun)

5. Milan Lucic – Edmonton Oilers

The Oilers could be forgiven for signing tough-as-nails playmaker Milan Lucic to a rich, seven-year, $42 million contract in 2016. After all, he had plenty of playoff experience, had won a Stanley Cup and his services were in huge demand. The team, with Lucic in the line-up, made the playoffs for the first time in a long time and went two rounds into the post-season before succumbing. Lucic was good, scoring 50 points in 82 games, earning his $6 million cap hit, for the most part. Lucic is still on pace to put up 50 points this season, but he has just nine goals on an underachieving Oilers squad which desperately needs secondary goal scoring. His deal doesn’t look so bad, right now, given that team leader and superstar Connor McDavid is only making $925,000 in 2017-18. The team will also have to sign budding star defenceman Darnell Nurse to an extension, as he is RFA. Next year, McD is in the first year of a contract that pays him $12.5 million annually, which will make Lucic’s $6 million, no-movement clause contract even more unattractive.

THE CANADIAN PRESS/Jason Franson

4. Alexi Yashin – New York Islanders

The Islanders just recently stopped paying Alexei Yashin $2.2 million dollars a year in dead money, the last payment of which was sent out in 2015. That was a full eight years after he last played for the Isles. Yikes! Yashin was the no. 2 overall selection in the 1992 NHL Entry Draft, and did register a couple of 40-goal seasons in his time with Ottawa before being dealt to the Islanders on draft day in 2001. The contract he signed was actually pre-salary cap era (10 years and $87.5 million in 2001) and wasn’t terrible based on his production, but the terribly enigmatic player would sometimes disappear in games, especially the ones that mattered. The buyout, which was negotiated under the terms of the new CBA (thus post-salary cap) netted Yashin roughly $17.63 million, at which point he packed his bags and took off for the KHL.

(AP Photo/Kathy Willens)

(AP Photo/Kathy Willens)

3. Wade Redden – New York Rangers

Glen Sather was back at it again in 2008. He handed Wade Redden a six-year, $39-million contract that summer – quite a lot for a defenceman whose play plummeted in his final two seasons with his former team, the Ottawa Senators. If Redden was still in his prime, the compensation he was gifted by Sather wouldn’t have been such an albatross. The fact was, though, that Redden was a borderline NHLer, who declined to 26 points in his first year of the contract (2008-09) and then 14 the next, before being put through waivers and was forced to spend a full two years in the minors while collecting his hefty paycheque. The contract was eventually bought out in 2012 and he was able to play another 29 NHL games before hanging up the skates.

(AP Photo/Frank Franklin II)

(AP Photo/Frank Franklin II)

2. Ville Leino – Buffalo Sabres

In the future, onerous contracts that get bought out early might get called “Doin’ the Leino.” Detroit signed Leino out of the Finnish Elite League as an undrafted free agent in his mid 20’s in 2008. He spent parts of two season with the Wings before heading to Philadelphia, where he had one successful playoff run during the 2010 playoffs, netting a surprise 21 points in 19 games. Leino then had a decent follow-up 2010-11 season, tallying 53 points in 81 games. As a UFA the following summer, Buffalo carted wheelbarrows full of money to him as he signed an outrageous six-year, $27 million contract under new owner Terry Pegula. Leino recorded 25 points in his first season, just six the following year (in an injury-riddled season), and then 15 points in 2013-14, in which he was regularly a healthy scratch. He was subsequently bought out and is now plying his trade with Vaxjo of the Swedish League.

THE CANADIAN PRESS/Darryl Dyck

THE CANADIAN PRESS/Darryl Dyck

1. Rick DiPietro – New York Islanders

This is the grand-daddy of all bad contracts and one that would probably be in the curriculum if there was a course on how to be a sports GM. In the 2006-07 season, the New York Islanders’ somehow decided it would be a great move to sign a goalie who had never recorded an NHL save percentage of .915 or better to a whopping 15-year deal. The pact given to Rick DiPietro was for a whopping $67.5 million, easily the least prescient and later deemed dumbest contract ever awarded in the NHL — possibly in all of pro sports. He was injury riddled and inconsistent and had barely played two full seasons worth of games across six years after being selected no.1 overall out of Boston University in 2000. For his entire career, he played a grand total of 318 NHL games and logged a pretty pedestrian .902 save percentage. He was finally bought out of his deal and tried (but failed) in a AHL tryout with the Carolina Hurricanes organization in 2013-14.

(AP Photo/Kathy Kmonicek, File)

(AP Photo/Kathy Kmonicek, File)