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In today’s salary cap world, it only takes one bad contract to handcuff your management team. That’s why it’s of the utmost importance for clubs to know exactly what to expect from a player before putting pen to paper, but that’s more easily said than done.

Sometimes, if a team has signed a mediocre-to-poor player to a fat contract with term attached, it’s in the club’s best interest to buy the player out. It takes a GM who’s willing to swallow his pride and admit his mistakes, assuming that it was he who signed the rotten contract in the first place.

Today we’re going to look at 15 players who are still costing their former clubs’ owners financial headaches. In most of these cases they’re causing cap issues as well, as buyouts count against the cap and most of the entries in today’s list are players who were bought out.

Other players appearing on the list are there because they have sustained serious or career-threatening injuries, and thus have been inactive for a long period of time. In these cases the team’s insurance would be on the hook for these salaries. In any case, neither situations are ideal for clubs that thought they were acquiring useful pieces for the future. Enjoy:

15. Stephen Weiss – Detroit

Winslow Townson-USA TODAY Sports

Winslow Townson-USA TODAY Sports

The Detroit Red Wings signed UFA center Styephen Weiss to a five year deal during the 2013 offseason, and it didn’t end well for them. After struggling through two injury-riddled seasons in Motor City, the Red Wings saw a buyout as their best option moving forward with Weiss, and they pulled the trigger on that decision on June 30, 2015, the day before free agency was set to open.

Weiss had shown promise early in his career when playing with Florida, but his regression had already begun by the time he went to Detroit. He never re-discovered the touch that made him successful in the infancy of his career, and as a result he’s now unemployed, yet still collecting a paycheck from the Wings (and he will be until 2020-21).

14. Rich Clune – Nashville

Perry Nelson-USA TODAY Sports

Perry Nelson-USA TODAY Sports

Most people will remember that Rich Clune couldn’t play well enough in the 2015-16 season to stick on the Toronto Maple Leafs roster, playing most of the season with the Marlies of the AHL. That’s where he is today as well, as the Maple Leafs have him buried in the minors. It’s possible that Clune has already played his last game in the league, which is a shame.

Clune’s inclusion on this list isn’t for his time in Toronto though, but rather Nashville. The Predators decided that a buyout was the best course of action after the 2014-15 season. Clune had just one year left on the deal, but as buyouts work the Preds are still paying him for the remainder of this season as well.

13. Brad Boyes – Florida

Kim Klement-USA TODAY Sports

Kim Klement-USA TODAY Sports

Brad Boyes is a veteran of 822 games, yet he never really seemed to get the respect he deserved while playing in the world’s best hockey league. The Florida Panthers bought out the final year of Boyes’ contract after the 2014-15 season, despite the relatively cheap $2.6 million cap hit and his decent production (he’d just registered 38 points in 78 games, in addition to having solid underlying numbers).

Boyes hasn’t officially hung up the skates yet, but he is without a contract right now, and the later it gets in 2016-17, the more unlikely it is to happen. Boyes has had a nomadic NHL career, playing for seven different teams so far. His best seasons were spent as a member of the St. Louis Blues, where he put up consecutive seasons of 43 and 33 goals.

12. Cody Hodgson – Buffalo

Kevin Hoffman-USA TODAY Sports

Kevin Hoffman-USA TODAY Sports

Cody Hodgson’s pro career looked extremely promising from the outset. The Vancouver Canucks draft pick was dealt to the Buffalo Sabres before the end of his rookie year, despite putting up 33 points in 63 games with Vancouver. The Canucks had a great team at this point, and Hodgson was having trouble finding a permanent spot in the top six, which is what he so desired.

Hodgson continued to develop with the Sabres, and things were going so well that the club decided to ink him to a six-year, $25.5 million contract extension. Hodgson had one more decent season with Buffalo before falling off a steep cliff production-wise. The Sabres exercised the buyout option on Hodgson after 2014-15, a season in which he put up only 13 points in 78 games. The Sabres will pay him through 2022-23.

11. P.A. Parenteau – Montreal

Ed Mulholland-USA TODAY Sports

Ed Mulholland-USA TODAY Sports

P.A. Parenteau signed a contract this past offseason with the New York Islanders, but was placed on waivers before the season began after not making the team out of camp. The New Jersey Devils took a chance on the 33-year-old, and the winger has already chipped in seven goals—not bad for a waiver wire pickup. With all this going on with Parenteau, some fans probably forget that he still collects a paycheck from the Montreal Canadiens organization.

After a disappointing 2014-15 season, the Canadiens decided they’d seen enough from Parenteau and felt it was necessary to buyout the final year of the winger’s contract. This is the last season in which the Habs are still on the hook for Parenteau, who has spent time on three different clubs already since departing the province of Quebec.

10. Mason Raymond – Calgary

Jerome Miron-USA TODAY Sports

Jerome Miron-USA TODAY Sports

The one they call “May-Ray” comes in at number 10 on our list. Mason Raymond is still collecting a paycheck from the Calgary Flames organization, despite having not played for them since the first half of last season. Raymond had a disappointing two seasons with the Flames, and the club opted to buyout the final year of Raymond’s deal this past offseason.

Raymond’s time in Calgary was defined by injuries, as he skated in just 86 games over his two years there. Most recently Raymond played for Anaheim, finding his way into four games early in the current season. After being placed on waivers and subsequently assigned to the AHL’s San Diego Gulls, Raymond and the Ducks agreed to terminate the remainder of his deal so that he could be with his family.

9. Chris Pronger – Arizona

via sbnation.com

via sbnation.com

Chris Pronger was having a great season in 2011-12 in Philadelphia when it grinded to a halt thanks to a concussion. Pronger would never play another game in the NHL, and today he is still being paid a salary despite being a certified member of the Hockey Hall of Fame.

The Flyers aren’t the ones on the hook for his salary, however, but the Arizona Coyotes are. In a pure-paper move, the Flyers sent the LTIR Pronger (plus Nicklas Grossman) to Arizona for Sam Gagner plus some picks in 2015. The ‘Yotes needed to reach the cap floor while not paying out of pocket (insurance covers LTIR cases), so it made sense for both sides. Pronger’s making nearly $5 million this season, but this is the final season he’ll collect a paycheck.

8. Thomas Vanek – Minnesota

Steve Mitchell-USA TODAY Sports

Steve Mitchell-USA TODAY Sports

Thomas Vanek is having a pretty solid season in Detroit so far in 2016-17. Despite battling injuries here and there, he’s put up 21 points in 26 games, a decent pace for any player, let alone an aging sniper (Vanek turns 32 in a few weeks). While he plies away at his trade in Motor City, many have likely forgotten that his name can still be found on the Minnesota Wild payroll.

The Wild elected to buyout the final year of Vanek’s contract this past offseason, meaning they are on the hook to pay the Austrian a total sum of $4 million over the next two seasons. The Wild were going to find themselves in some cap trouble if they didn’t do this, so the move made some sense. Still, though, it’s rare a player of Vanek’s ilk gets bought out in the heart of his career.

7. Roberto Luongo – Vancouver

Steve Mitchell-USA TODAY Sports

Steve Mitchell-USA TODAY Sports

Some will remember that the Vancouver Canucks retained salary when they dealt Roberto Luongo to the Florida Panthers, while others may have forgotten by now. Either way, Luongo still indeed collects a check from his former employer out on the West Coast, and that will be the case until he retires. Oh, Vancouver, we can always count on you to screw up your crease situations.

His current contract pays him through 2021-22, which takes him to the age of 41. If he chooses to retire before the contract expires, the Canucks will be off the hook for whatever is left. However, if I were making the type of coin Luongo is to play the game I love, I wouldn’t retire before my contract’s expiration, that’s for damn sure.

6. Tim Gleason – Toronto

Geoff Burke-USA TODAY Sports

Geoff Burke-USA TODAY Sports

As far as I can tell, Tim Gleason is no longer playing professional hockey anywhere. According to Hockey DB, his last pro games were played in 2014-15 with the Washington Capitals. Lucky for Gleason and his family, he still to this day collects a salary from the Toronto Maple Leafs, despite having only ever played 39 games for the club back in 2013-14.

The Leafs decided to buyout the remaining two years of Gleason’s contract in the summer of 2014, meaning they would have to pay the defenseman a total of $5.7 million over the course of the following four seasons. Toronto will finally be off the hook from Gleason at the end of 2017-18, when Gleason will already have been out of the league for about four years.

5. R.J. Umberger – Philadelphia

Jerome Miron-USA TODAY Sports

Jerome Miron-USA TODAY Sports

I think we all remember R.J. Umberger. He was a veteran of 779 NHL games, spent entirely with Philadelphia (on two separate occasions) and Columbus. He enjoyed a few fairly productive seasons in that stretch, highlighted by a 57 point campaign with the Jackets in 2010-11. He was dealt back to Philly (where he had started his career) in 2014, but had by then almost completely lost his scoring touch.

The Flyers gave Umberger two seasons to try and figure it out, but he simply never got back to where he was. The Flyers bought out the remainder of the contract—which only had one year left on it—this past offseason. As such, Philly is paying Umberger $1.5 million both this season and the next. His NHL days are likely over.

4. Matt Carle – Tampa Bay

Kim Klement-USA TODAY Sports

Kim Klement-USA TODAY Sports

Veteran defenseman Matt Carle officially announced his retirement back in November after a career that saw him play 730 NHL games for four different franchises. The Alaska native played six games with the Nashville Predators this season, but ultimately decided that the daily NHL grind was too much for him and his family at this juncture.

By retiring Carle forfeited was was left of his $700,000 salary from this season, but perhaps that blow was softened by the fact that he still collects a paycheck from the Tampa Bay Lightning. The Bolts are on the hook for $1.83 million per season through 2019-20, which is nearly 150% more than the salary he was receiving to play for the Preds this year. Yep, that definitely makes the decision a little easier.

3. Andrew Ference – Edmonton

Charles LeClaire-USA TODAY Sports

Charles LeClaire-USA TODAY Sports

Former Oilers captain Andrew Ference hasn’t played a game with the club since 2015-16, and even then he only saw action in six games early on. Now, Ference isn’t technically costing the Oilers’ salary cap for this season, as he’s on the LTIR, but should he receive a clean bill of health at any point this season, he would cost the Oilers.

Lucky for them there is no NHL protocol that forces teams to reevaluate these players mid-way through a season, and Ference has been shut down for the remainder of the year. He’s also on the last season of the four year deal he signed with the Oilers in the 2013 offseason, meaning that he will almost certainly be announcing his retirement at season’s end. Thanks for the memories, Ference.

2. Dave Bolland – Arizona

James Guillory-USA TODAY Sports

James Guillory-USA TODAY Sports

The Dave Bolland case in Arizona these days is sort of a weird one. While it’s easy to see why the Coyotes felt safe taking on Chris Pronger’s contract (he’d already announced his retirement), the Bolland contract seems a little risky. Officially Bolland’s ailment is listed as a lower-body injury, and there is no timetable for his return. Now, perhaps the ‘Yotes know something we don’t, but there’s still three years left on the $5 million/year cap hit. It would have to be one heck of a LBI to keep him out for that long.

Scoring twice in 17 seconds to win a Stanley Cup will certainly raise anybody’s stock, and that’s what Bolland pulled off in 2013 with the Blackhawks. Since then Bolland has really done a whole lot of nothing at the pro level, and it is entirely possible he’s no longer good enough to play in the NHL, healthy or not.

1. Alexander Semin – Carolina

Jean-Yves Ahern-USA TODAY Sports

Jean-Yves Ahern-USA TODAY Sports

Alexander Semin’s reputation has always plagued him during his career. No one was ever able to deny his talent level as elite, yet the former 40-goal scorer has already been spit out the bottom of the league at the age of 32, playing his days out in the KHL back in the motherland. Semin first signed a one-year deal with the Hurricanes for the lockout-shortened 2012-13 season, and he put up in impressive 44 points in 44 games.

This convinced GM Jim Rutherford to sign Semin to a long-term contract at a pretty hefty price tag ($35 million over five years). The ‘Canes bought out the last three years of the deal after two disappointing seasons in Raleigh, ergo they will be sending a check to Semin through the 2020-21 season. Ouch.

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