The Worst NHL Free Agent Contracts Since 2005

With the NHL free agent frenzy coming up in nearly a week, we look back to the worst contracts given out to free agents since 2005. Each year it seems, one player in the free agent market is severely overpaid for, causing fuss for that team down the road. Often, buyouts are the result of these terrible contracts, and careers can easily end with such a signing. Below, in no particular order, are the worst free agent contracts in the NHL since 2005. There are plenty of these type of contracts, but we feel that these are the worst of the worst.

Ville Leino

6 Years, Worth $26 Million with the Buffalo Sabres in 2011.

When Ville Leino came to the NHL from Finland to play with the Detroit Red Wings, there were somewhat great expectations of him. It didn’t turn out as expected in HockeyTown, as Leino scored just nine goals and 16 points in 55 games. He was then traded to the Philadelphia Flyers where he flourished. In the Flyers run to the Stanley Cup Finals, Leino picked up seven goals and 21 points in 19 games. It didn’t stop there, as in 2010-11 he scored 19 goals and 53 points in his 81 games. Once his contract was up on July 1, 2011, he was suddenly the most wanted free agent on the market. That’s where Buffalo made a crucial mistake.

(Timothy T. Ludwig-USA TODAY Sports)
Ville Leino managed to go his entire 2013-14 season without scoring a single goal. (Timothy T. Ludwig-USA TODAY Sports)

On July 1st, 2011, the Buffalo Sabres signed Ville Leino to a multi-year contract. For $27 million, Leino would be a Sabre for six years. The Sabres were thrilled to get such an exciting player on their roster. But, that’s where the excited ended. In 71 games the next season, he scored just eight goal and 25 points, far short of what the Sabres were expecting of him. But it got worse. In 2013-14, he played 58 games without scoring a single goal. That’s when the Sabres knew they had made a great mistake. That summer,  Buffalo used one of their two compliance buyouts to get rid of the three years remaining on his contract, a $4.5 million cap hit. That spelled the end of Leino’s NHL career, as he now plays for the KHL’s Zagreb Madvescak. In the end, Buffalo overpaid a player who had only had one good NHL season, and it came back to bite the in the rear.

David Clarkson

7 Years, Worth $36.75 Million with the Toronto Maple Leafs in 2013.

David Clarkson was an undrafted prospect coming out off the Kitchener Rangers system in the OHL when New Jersey Devils GM, Lou Lamoriello, decided the take a chance on the rugged forward. He came into New Jersey’s system in 2005-06, playing in the AHL for two seasons while racking up big penalty minute numbers and, surprisingly, some half decent goal production. He became a full time NHL player in 2007-08, earning himself 183 PIM in 81 games. It was in 2011-12 when became a sought after free agent. He scored 30 goals in a year which saw the Devils reach the Stanley Cup Finals, then another 15 in the lockout shortened season. All of a sudden, he was the best available free agent in 2013.

Maple Leafs David Clarkson
David Clarkson was expected to score goals for the Leafs, but they didn’t realize that he is a grinding player. (John E. Sokolowski-USA TODAY Sports)

The Toronto Maple Leafs saw someone who grew up in the city idolizing the team. Clarkson seemed to be just what the Leafs needed, someone who can score goals, while also playing a very physical role. So, they signed Clarkson for seven years worth $36.75 million, or $5.25 million per year. Each side came into the new season very excited and expecting great things. Well, great things did not come. Clarkson scored a grand total of 15 goals and 26 points in his 118 games as a Maple Leaf. Expectations may have seen him scoring 40 goals and upwards of 60 points in that time. But, that’s not Clarkson’s fault. It’s Toronto’s, for looking solely at the past two seasons of a 29-year-old. They also put him in a scoring role, as opposed to the grinding role he was successful in. Some bad decisions and lofty expectations led to a terrible contract by the Toronto Maple Leafs, one of the worst ever.

Wade Redden

6 Years, Worth $39 Million with the New York Rangers in 2008.

Wade Redden was a 2nd overall draft pick in the 1995 NHL Entry Draft by the New York Islanders, but would never hit the ice in their jersey. He was sent back to the WHL after his draft year and subsequently felt to the Ottawa Senators. He would spend 11 fantastic years as a Senator, until he contract expired making him a sought after free agent. In his 11 years, Redden would score 101 goals and 410 points in 838  games. Frankly, he looks like he could be on his way to a possible Hall of Fame career at only 31 years of age. That’s why the Rangers wanted to pick him up for a possible Stanley Cup run.

On July 1st, 2008, the New York Rangers would pay up for Redden, signing him for six years for $39 million, for an annual cap hit of $6.5 million. Both sides were very excited for the future of the organization. When the season came, the Rangers quickly became disappointed and frightened. In his first two seasons, Redden would score five goals and 40 points in 156 games, no where near the production that was expected of him. In return, New York demoted him into the AHL for the next two seasons before the would buyout the final two years of his contract. After that, Redden would play a few games for St. Louis and Boston before retiring. For some reason, Redden’s career went downhill very quickly at just 31 years old. For the Rangers that meant their name would be attached to one of the worst free agents signings in the past decade.

Scott Gomez

7 Years, Worth $51.5 Million with the New York Rangers in 2007.

Scott Gomez was drafted out of the WHL’s Tri-City Americans in 1998 by the New Jersey Devils at 27th overall. He was regarded as one of the premier playmaking prospects in the game. He made his NHL debut in 1999-00 when he scored 19 goals and 70 points in 82 games, enough for him to win the Calder Trophy as the league’s top rookie. However, he would only play seven years in New Jersey, his best being in 2005-06 when he scored 33 goals and 84 points. In July of 2007, his contract would come up, making him one of the best free agents of the year. That’s when the rangers jumped into the situation.

Scott Gomez Canadiens
The Montreal Canadiens finally bought out Gomez after he had two disastrous seasons. (Icon SMI)

The New York Rangers signed him for seven years worth $51.5 million, for a cap hit of $7.35 million each year. He played very well in his two seasons with the Rangers, registering a total of 128 points in 158 games. But New York likely realized, just in time, that Gomez was on the downswing of his career, and his contract wouldn’t be easy to deal with for five more years. So they traded him to Montreal, earning their current captain, Ryan Mcdonagh, in return. After an abysmal third season with the Habs, Gomez was bought out and his career looked to be over. He then spent two years between San Jose and Florida, before signing back with the Devils last year. Remarkably, he flourished in his 58 games, putting up a very respectable 34 points. Now, it looks like at 35 years old, he may still have a few seasons left in his NHL career. Between that though, is his terribly overpaid contract, again signed with the New York Rangers.

Disagree? Let us know which free agent contract since 2005 in the very worst!