The past speaks volumes when signing a free agent or extending a current player, especially if it comes with a pay raise. Sometimes it's a reward for how well the player has produced, and nothing will change going forward in terms of production. On the other hand, a player will begin to regress but will have signed based on prior performance. That's when you get bad contracts and it's difficult to get rid of them.
Just last year's free agent class is a good example of players getting signed into their 30s and being paid without the notion of regression in mind. Most of the long term deals (5+ years) were awarded to players 29 and over. This was mainly due to a thin batch of talent available for signing last Summer, which drove their price up because of demand. It is also due to players needed job security and one good way to get that is through longer deals. Unfortunately though, many of these players had their prime years behind them.
There are a couple of reasons why a contract is bad, but it mostly comes down to the production they make based on their salary. For example, 30-40 point forwards are quite common in the NHL and should cost next to nothing to roster. For some older players though, good and productive seasons are seen as an infinite commodity even though regression is usually imminent, so they sign long term deals valued at what they've done in the past. What makes a lucrative contract for an average player even worse is if it has extended term on it.
15 Brent Seabrook
The Hawks' stalwart on defense and long time member of the top pair with Duncan Keith, Seabrook is still a decent player. Maybe $6.875M is a bit much, but can be justified with his experience, his defensive game, and his decent contribution to offense. What makes this contract bad is the term. Already 32, this contract has him locked up until 2023-24 with a no-movement clause until 2021-22. The Hawks already devoted quite a considerable amount of their salary cap in their top two players Patrick Kane and Johnathan Toews, and still have to re-sign Artemi Panarin in two years.
Contracts like Seabrook's and Marian Hossa's are the reason the revolving door continues to swing in Chicago. It could also mean the downfall of their modern dynasty.
14 Zach Parise
Parise and Ryan Suter were poached by the Wild a few years back, and signed the exact same contract: 13 years at just over $7.5M per year. The Suter signing has so far paid dividends, since he's the epitome of consistency and efficiency on a relatively young Wild blue line. His point production is still there at 32 years old, and his time on ice has started tapering off to accommodate for his age. Parise on the other hand has hardly brought what he once had with New Jersey. Due in part to missing 48 games in the past five seasons, it seems Parise is now playing second fiddle in a young but maturing forward core that has passed him in terms of production. Let's hope he can have one full healthy season sometime soon, and can still produce like he once did.
13 Andrew Ladd
Ladd was fantastic on the Jets. He brought that first line with Blake Wheeler and Bryan Little together perfectly, and was a good reason they made the playoffs in his most successful season points wise. Although he's won two cups away from Winnipeg, he played his best hockey while on that team. The Islanders thought that success would be extended to Brooklyn, but so far couldn't be more wrong.
They signed him to a stunning 7 year, $5.5M per year contract. Brought in to help John Tavares on that first line by playing at a high tempo like he had in the past, he was anything but in his first year. With only 31 points in 78 games, the Islanders' system may be too foreign for Ladd.
12 Bobby Ryan
It's hard to rationalize why the Senators offered Ryan this contract. The season prior to his extension, he was fifth on the team in points and fourth in goals, with the young Kyle Turris breaking out and prospects like Mark Stone and Mike Hoffman on their way to full time NHL gigs. Having finished the 2013-14 season with 48 points in 70 games (only 23 goals), Ryan signed a seven year deal with a cap hit of $7.25M. This is a player whose best years are far behind him, and while on another team, playing on a line with one of the best duos in hockey in Ryan Getzlaf and Corey Perry. His offensive talent was totally lacking this year as well, with only 25 points in 62 games.
11 Corey Perry
Out of Ryan Getzlaf, Ryan Kesler, and Perry, the worst of the 32 year old forwards on no-movement clause contracts has to be the most expensive one in Perry's. With so many younger players looking for extensions in the next few years, especially their franchise goalie John Gibson, Perry's contract will bring with it a potential loss of talented youth. He's making $8.625 million until 2021-22, and his no-movement clause is in effect the whole way through.
Though his shooting percentage was way below career average this past season (only 19 goals, 53 points as a result), it's hard to see him get back into the 65+ point range at his age that helped justify the contract for so many years. The saving grace is Perry is a proven playoff performer.
10 David Backes
The Bruins were more than happy to sign the Blues' long time captain. A hard working power forward who was usually good for close to 60 points per season, he was just what the team needed to balance out their now young core of skilled players. Unfortunately for Boston, they felt the need to give a 32 year old a 6 year, $36 million contract. The more intriguing part is that Backes didn't even have a good contract year, with only 45 points in 79 games on a Blues team that was going through a changing of the guards in terms of forwards. With a no-movement clause for two more years, we'll see how Boston handles this contract when it comes to resigning their younger players.
9 Loui Eriksson
Vancouver is stuck in a rebuild and they have to deal with a contract like this one. At 31, Eriksson is coming off by far one of the worst seasons of his careers. Bad seasons are one thing, but to be making $6M per year, and have a no-movement clause for one more year, must make this contract even more regrettable. Even after his no-movement clause no longer applies, he still has a no-trade clause for two seasons. The former 30 goal scorer was brought in to shine with the Sedin twins only to have 24 points in 65 games this past season. For a team that would rather trade older players for prospects and picks, this contract probably won't get much in return.
8 Aaron Ekblad
This is an interesting contract for the 21 year old first overall pick. After two promising seasons in the NHL coming right out of juniors, Ekblad looked to be the real deal. This year saw him take a step back though, and he had only 21 points in 68 games after missing time with a concussion and a neck injury. His extension has him signed for the maximum of 8 years and will have him making $7.5M per year.
This contract has the potential of going the way P.K. Subban's did. Subban got traded in part so the Montreal Canadiens wouldn't have to have his no-movement clause that would've come into effect a few days after the trade. If Ekblad doesn't pan out the way the Panthers had hoped, they may try moving him before his no-movement clause comes in effect as well (2021-22, the season he'll be turning 26). But at $7.5M per year, it may be difficult depending how he plays then.
7 Matt Moulson
The Sabres are finally trending upward again but have a terrible contract in the way before they can resign their younger players. With Jack Eichel and Sam Reinhart being RFA in two years, and Evander Kane hitting free agency that same offseason, Moulson's contract may mean they can't be as competitive as they can because of their cap space. He's still under contract until 2019-20 at the unfortunate cost of $5 million per year. This is a player whose best season is a ways away, and signed this extension at 31 years old. Though slightly better than the 21 points he put up last year, the 32 points from this past season really don't flatter him considering the amount of money he's making.
6 Travis Zajac
It must be an awkward situation for the Devils to have a 40-45 point player making almost as much as the 25 year old (and potential point per game production) Taylor Hall. Even more awkward is that, at 32, Zajac is signed until 2021-22. Making $5.75 millionper year, Zajac as well as the Devils' glory years, are far behind them. Stuck with the low scoring style they've been plagued with for years now, having so much cap space allocated to a player who offers as much production as someone making half that salary is definitely detrimental. Thankfully for the Devils, he only has a no-trade clause so hopefully this contract is off their books when they have more capable players to fill their lineup.
5 Erik Johnson
Assuming the Avalanche don't blow up this roster and get rid of all their young players not named Nathan MacKinnon in order to rebuild, the Johnson contract could put a spanner in things. With Gabriel Landeskog, Matt Duchene, and Tyson Barrie all due for extensions while Johnson is still under contract, as well as prospects needing extensions by that time as well, they may find it difficult to move a 30+ year old who's making $6 million per year until 2023-24. He tends to miss time at least once per season, but nevertheless has only had three seasons of over 30 points, with two of those being 39 points. The Avs definitely need upgrades throughout their blue line.
4 Milan Lucic
Brought in to protect Connor McDavid and be a physical presence on that first line, Lucic was quickly pushed down the depth chart in favor of Patrick Maroon. Lucic is making $6M per year until he's 34 and at 29, is already showing signs of not being able to keep up with the speed of the game. Maroon, making an incredible $1.5M per year, had 42 points (27 goals) compared to Lucic's 50 points (23 goals). Yes, Maroon had McDavid to help him out but that's in large part due to Maroon being able to keep up with the superstar. Also worth noting is that Lucic is now apparently a power play specialist, since half his points came on the man advantage (with McDavid's unit).
3 Ryan Callahan
This is a classic case of intangibles scaring a general manager into an unnecessarily expensive contract. Brought in via trade (for Tampa legend Martin St. Louis, no less), Callahan was praised as a leader and for the sandpaper style of play he brings to the table. But do those qualities mean that, at 29 years old and with a career high of 54 points, Callahan had to be offered $5.8M per year for 6 years? Not only that, but he also has a no-movement clause until the end of next season. His first year of the deal saw him get 54 points again but since then the former Rangers captain has had only 32 points in 91 games these past two seasons. For a team that has so many good young players to resign, having so much in cap hit in a player that only helps out in the locker room seems a bit questionable.
2 Marc Staal
The Rangers just bought out Dan Girardi's brutal six year, $33M contract. Unfortunately, another overpaid defenseman is still stuck in New York. At 30 years old, Staal is signed until 2020-21 for $5.7 million per year. Of course, the no-movement clause rears its ugly head again, this time in effect for the entirety of his contract. Even without the clause, it's unlikely any team would want Staal on their team for that price. Not known for his point production, it's still worth noting that his point production has decreased, now with consistent seasons of 20 points and under. His bread and butter is on the defensive side of things, but has been bad in that regard as well these past few years. The Rangers would love an out on this deal so they could bring in their next overpaid free agent.
1 Dustin Brown
From playing on one of the best contracts in the league to signing an extension and having one of the worst. The former Kings' captain was a wrecking ball for them in his prime, playing like the ultimate power forward and helping them win two Stanley Cups. Consistent 50+ point seasons, as well as 20 points in 20 games en route to their first cup in 2012, Brown was a steal at just under $3.2M per year.
Then came one of Dean Lombardi's many blunders as general manager. At 29 years old, Brown signed an eight year, $47 million contract. Since signing his extension, he's had seasons of 27, 28, and 36 points. A terrible waste of cap space for a player that can be producing like that for next to nothing.