The 5 Biggest Losers of 2014 NHL Free Agency So Far

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The 5 Biggest Losers of 2014 NHL Free Agency So Far

2014 NHL Free Agency Losers
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The 2014 NHL free agency period has seen a ton of dreadful contracts handed out to mediocre players. In other cases, teams that didn't hand out too many bad contracts went wrong by standing pat when they needed to make improvements. Here are the 5 biggest losers of the free agency period so far.

5. Calgary Flames

Calgary Flames
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5. Calgary Flames

Calgary Flames
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The Calgary Flames vastly overpaid a fringe NHL defenseman in Deryk Engelland and lost one of their only solid offensive players in Mike Cammalleri. They signed Jonas Hiller — a middling goaltender who the Anaheim Ducks were happy to let go of — and Mason Raymond, but there's not much doubting that Calgary spent a big chunk of money in free agency without really getting anywhere.

4. Detroit Red Wings

Detroit Red Wings
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4. Detroit Red Wings

Detroit Red Wings
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The Detroit Red Wings missed out on all their primary targets. It doesn't seem like Detroit is the attractive free agent destination of years past; perhaps the league's players have recognized that the Red Wings are a team on the downswing. Henrik Zetterberg and Pavel Datsyuk are nearing the twilight of their careers, and Detroit did nothing to surround them with quality pieces.

3. New York Rangers

New York Rangers
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3. New York Rangers

New York Rangers
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The New York Rangers lost a number of players who played fairly large roles for them last season, including Brian Boyle, Benoit Pouliot and Anton Stralman. They got older and worse by agreeing to deal with the rapidly-declining Dan Boyle.

2. Florida Panthers

Florida Panthers
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2. Florida Panthers

Florida Panthers
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During this year's free agency period, the Florida Panthers inked a deal that had the rare distinction of being immediately tossed into the "worst contract in the NHL" discussion before the player in question had even played a game with his new team. That player, of course, is Dave Bolland, and the five years and $27.5M that the Panthers gave him is utterly beyond explanation.

1. Washington Capitals

Washington Capitals
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1. Washington Capitals

Washington Capitals
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Brooks Orpik's deal with the Washington Capitals puts the word "awful" to shame; it's not often you'll see the same terms as Bolland received from Florida offered to a third-pairing defenseman. The Capitals also overpaid Matt Niskanen, although he will at least help their cause on the ice. On the whole, Washington burned an almost hysterical amount of money just to get a tiny bit better.

Sean Sarcu is a Chicago Blackhawks writer for RantSports.com. Follow him on Twitter or add him to your network on Google.