The NHL’s salary cap shows no mercy. Even one error in judgment by a general manager can handcuff a team, rendering it incapable of making roster changes and forcing it to ice something less than its best possible lineup.

Of course, there are varying degrees of bad deals. Some are short-term and will be off the books in the next year or so. Others seem bad when viewed over the long term, but they provide decent value in the here and now.

Then there are the dogs that are too ugly to dress up and too painful to overlook. Here’s a snapshot of the league’s worst deals right now.

Andrew MacDonald, Flyers

Cap hit: $5,000,000 (through 2019-20)

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This contract might top the list of reasons why Paul Holmgren is now the former GM of the Flyers. As if sending two picks (one second rounder and one third) and a prospect to the Islanders at the 2014 trade deadline in exchange for the now 29-year-old defender wasn’t a complete waste of assets, Holmgren doubled down by signing MacDonald to a six-year, $30 million deal. Nice for the player, who was making just $550,000 on his previous contract, but a gross overpayment by Holmgren who completely misjudged MacDonald’s abilities when removed from the protective bubble he enjoyed on Long Island.

Exactly how gross became apparent this fall when the Fyers waived MacDonald and then buried him and his deal in Lehigh Valley of the AHL where he’s now the highest-paid player in the minors. In fact, he’s pocketing more than top-pair NHL stars like Justin Faulk, Ryan McDonagh, Kevin Shattenkirk and Roman Josi.

Although he’s been fairly effective with the Phantoms, earning 10 points in 20 games, MacDonald has been bypassed in favor of Davis Drewiske and Shayne Gostisbehere when the Flyers needed reinforcements on the blue line. It’s pretty clear that he’ll continue earning that tidy sum while riding the buses.

Dustin Brown, Kings

Cap hit: $5,875,000 (through 2021-22)

Brown is entering the second season of an eight-year, $47 million contract that seems to get worse every time he steps on the ice. Though he has captained the Kings to a pair of Stanley Cup championships, his personal performance is in a steep decline. He hasn’t hit the 50-point mark since 2011-12 and has scored just 27 points each of the past two seasons. With only seven points in his first 23 games this season, he'll be lucky to equal those paltry totals. He’s been called out by coach Darryl Sutter but has just one goal in his past eight games and has seen his ice time decline steadily, with a season-low 12:44 coming in a 2–1 loss to the Lightning last Wednesday. At this point, Brown is a spare part on a team that’s looking to him for leadership.

Zach Parise, Wild

Cap hit: $7,538,461 (through 2024-25)

Nothing wrong with giving dollars and term to truly elite players, someone like Ryan Suter for example. But Parise, who was given an identical deal to Suter and is on the books for $9 million this season, is a solid player who’s being paid like a superstar. And that’s how the 31-year-old will continue to be paid into his 40s even as his game goes into a sharp decline. The Wild went 4-3-1 during his recent stint on the IR, and while that’s a very small sample, it hints at his impact. Minnesota is a better team when Parise is in the lineup, but take him out and his absence isn’t felt as keenly as if Suter or Mikko Koivu were sidelined. And, yes, another team likely would have offered him a similar deal in free agency, but that doesn’t make it a smart investment.

Marian Gaborik, Kings

Cap hit: $4,875,000 (through 2020-21)

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Even with three goals in his last three games, Gaborik’s numbers—five goals and seven points in 23 games—are lousy for a player who is being paid to play first line minutes for a contending team ... and they only look worse when you consider that he’s actually making $6.075 million this season and next. There’s little spark in the play of the 33-year-old and signs of his old speed and creativity are few and far between. It looks like last year’s 27-goal performance was an aberration rather than a return to form after two injury-plagued campaigns, making this gamble another painful error by GM Dean Lombardi.

Dave Bolland, Panthers

Cap hit $5,500,000 (through 2018-19)

It’s easy to understand why Panthers GM Dale Talon was so high on bringing Bolland into the organization. Bolland’s scrappy leadership was an element that could come in handy on a team relying heavily on youth while it was being rebuilt. But when a guy is the highest-paid forward on the team, he needs to bring more to the table than intangibles. On that count, Bolland has failed miserably. After scoring just 23 points last season, he has one goal and four assists in 18 games this season and has become a frequent visitor to the press box. At 29, and with three more seasons to go on his deal, it’s unlikely that Bolland will ever elevate his play to a level that merits this salary.

Bryan Bickell, Blackhawks

Cap hit: $4,000,000 (through 2016-17)

Bickell’s Cinderella success story during Chicago’s 2013 Stanley Cup run earned him a four-year, $16 million deal. That contract is more than reasonable if he is a top-six winger for the Hawks, but not so much for a guy skating with the Rockford Ice Hogs. Bickell’s struggles at the NHL level led to him being waived and later demoted to the AHL, and while he’s had some success there—nine points in 10 games—his inability to contribute in Chicago makes him a painful drain on the Blackhawks’ cap. Coach Joel Quenneville has been complimentary of Bickell’s work in the minors, suggesting he may get another shot at the show before long, but it’s hard to imagine him living up to his paper.

Brooks Orpik, Capitals

Cap hit: $5,500,000 (through 2018-19)

A $5.5 million cap hit is massive for a 35-year-old defensive-minded second-pairing defender whose career is in decline. In fact, only 24 blueliners earn more than Orpik, whose value has been diminished even further while he’s on IR (lower body injury). Nate Schmidt has stepped into his place on the penalty kill—where Orpik primarily earns his keep—and been more effective as a shot suppressor while counting just $812,500 against Washington’s cap. With three more years to go on this deal, and his role potentially shrinking, Orpik is a massive drain on this team’s limited resources.

David Clarkson, Blue Jackets

Cap hit: $5,250,000 (through 2019-20)

It says all you need to know about Clarkson’s value that he was traded by the Maple Leafs to the Jackets last season for Nathan Horton, a player who is likely to never skate again in the NHL.

The deal made sense for Columbus, if only because it gave the Jackets a body they could potentially count on to play, but his $5.25 million annual cap hit (which includes two seasons where he’ll earn $7 million in actual salary) is grossly inflated compared to his actual value. Clarkson has just one assist in eight games this season, giving him 27 total points since he signed this seven-year, $36.75 million deal back in 2013. Now 31, it’s hard to imagine him ever approaching the 30-goal, 46-point heights he achieved with the Devils in 2011-12.

Jordan Staal, Hurricanes

Cap hit: $6,000,000 (through 2022-23)

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Though $6 million isn’t a ton of money to invest in a top center, Staal isn’t exactly that, is he? Nor is he really much of a No.2 or even a top-notch No. 3 for that matter. He doesn’t score much—he has just eight points through 23 games this season, which is well off last season’s pace when he managed just 24 points in 46 games. And while he’s still dynamite on the draw, he’s far from being a high-end defensive pivot. After earning Selke Trophy votes in each of his first seven seasons he hasn’t received a sniff of consideration in any of the past three. He’s overpaid by half now, and still has seven years to go on a deal that’s only going to look worse.

Vincent Lecavalier, Flyers

Cap hit: $4,500,000 (through 2017-18)

Lecavalier paid decent dividends (20-17-37 in 69 games) in the first season of the five-year, $22.5 million deal he signed with the Flyers in the summer of 2012, but since then he’s been reduced to spectator status. He’s skated in just 64 games since the start of the 2014-15 season, and has spent all but seven in the press box this season, a victim of his slowing feet and increasing instances of poor puck management and inexplicable defensive decisions. Having lost the faith of the coaching staff, he’s likely to ride out the majority of this costly deal why wearing a suit instead of pads.

Note: All salary info courtesy General Fanager.

The numbers game

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