5 of the Worst NHL Free Agency Contracts of All Time

Often general managers regret some of the deals they made on the open market. Here we’ll highlight five of the worst NHL free agency deals. Some of these deals didn’t work out because of injury, but that’s the risk you take when you hand out these big money contracts.

Three New York Rangers signings made this list, meaning new general manager Chris Drury may want to tread lightly in free agency this year. 

David Clarkson (Maple Leafs) – 2013 (7 years/$36.75 million)

There’s always a risk when you try to overpay a player that plays on the physical edge. David Clarkson was signed to drive the net and play alongside some of the team’s high-skilled forwards, but injuries ultimately derailed his career. He had a successful tenure with the New Jersey Devils for seven seasons, but there was always a buyer beware tag with Clarkson, who didn’t live up to his deal with only 26 points in 118 games for the Maple Leafs. The NHL is a physical league, and players that bring that edge often have their careers cut short.

Brad Richards (Rangers) – 2011 (9 years/$60 million)

The New York Rangers make their first appearance on this list, and there were a lot of questions about the term they gave to Brad Richards. The drama surrounding teams making pitches to Richards back in 2011 was crazy, but those who missed out on his services are likely thankful. Richards was a dominant player for the Tampa Bay Lightning and Dallas Stars, but his legs slowed down, and he didn’t fit in with the Rangers. The center saw his ice time decrease with the club throughout the first three seasons of his deal, which eventually saw him bought out by the franchise after the 2013-14 season. 

Scott Gomez (Rangers) – 2007 (7 years/$51.5 million)

Much like Richards, signing Scott Gomez in 2007 wasn’t something that turned out well for the Blue Shirts. Gomez had some incredible seasons with the New Jersey Devils, but things went downhill after signing with the Rangers. Gomez was still a solid player for New York; he just didn’t live up to the lofty expectations that his contract came with. Despite lackluster point totals for Gomez, the team was still able to deal his contract to the Montreal Canadiens and receive a good return. Sometimes, general managers get lifelines from their counterparts, and that’s what the Rangers needed. Montreal would grow to regret the trade. In his first three years in Montreal, Gomez scored only 21 goals. 

Ilya Bryzgalov (Flyers) – 2011 (9 years/$51 million)

The first goalie to crack this list is Ilya Bryzgalov, one of the most fascinating interviews in NHL history. Bryzgalov showed promise after having a nice run with the Arizona Coyotes, but this contract is one that didn’t age well for the Philadelphia Flyers, despite their dire need in goal. Two years into his deal, the Flyers bought out the Russian netminder and are still paying him until 2023-24. Goalies can be unpredictable, and we’re seeing something similar play out with Sergei Bobrovsky in Florida right now. 

Wade Redden (Rangers) – 2008 (6 years/$39 million)

When a defenseman loses their footspeed, it’s hard for them to live up to their contract, and that’s what happened with Wade Redden after signing long-term with the Rangers. In his prime, Redden was an essential part of the Ottawa Senators, but things trended downward after signing with New York as a 31-year-old. The big defenseman was bought in 2013 after spending time in the AHL, and what’s clear is that the Rangers should probably think twice before handing out big tickets in free agency.