The five worst free-agent signings of the salary cap era

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Good players aren’t really associated with their contracts, are they?

Quick: tell me the dollar figures and term of Connor Hellebuyck’s current contract. Or Victor Hedman’s. Or Ryan O’Reilly’s. And so on. We associate successful players with what they’ve won, from championships to individual accolades, not with what they’re paid.

But players who go bust on major contracts with big term and AAVs? They’re forever associated with their bad contracts. To speak one of their names is to elicit a groan from a fan of that player’s team and start a conversation on how bad the contract was.

Don’t believe me? You will after perusing my choices for the five worst UFA contracts of the NHL’s salary cap era.

Honorable mentions: Loui Eriksson 2016 (VAN), Jeff Skinner 2019 (BUF), Milan Lucic 2016 (EDM), Dave Bolland 2014 (FLA), Scott Gomez 2007 (NYR), Christian Ehrhoff 2011 (BUF), Nathan Horton 2013 (CBJ), Karl Alzner 2017 (MTL), Andrew Ladd 2016 (NYI)

5. Jeff Finger, 2008, Toronto Maple Leafs

4 years, $3,500,000 AAV

If you’re familiar with the honorable mentions above, you know plenty of bad contracts were pricier, longer and generally hurt their clubs worse than the Finger deal. But it has to crack the top five because of how downright perplexing it was even at the time. Finger, a former eighth-round pick, only had two NHL seasons and 94 games to his name when he hit the market in 2008 as a UFA. Then-Leafs GM Cliff Fletcher targeted Finger believing he had broken out as a shutdown defenseman who could help the Leafs grow into contenders.

As the legend has it, some deeper research into the quotes and justifications from Fletcher unearthed pretty strong evidence that Fletcher confused Finger with Avalanche teammate Kurt Sauer. Fletcher championed Finger’s shutdown ability in the playoffs … when Finger had been healthy scratched five times in the playoffs. Seriously, the breakdown from Dan Tolensky here is must-read.

As for Finger and his $14 million contract? He played two seasons and 105 games in a Leaf uniform and never even suited up in the NHL again after that.



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