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12 Worst Free Agent Signings in NHL History

Hockey
12 Worst Free Agent Signings in NHL History

There are worse things in the world than being an unrestricted free agent in the National Hockey League. You circle July 1 on your calendar and wait for overeager general managers to overvalue your services and throw copious amounts of cash your way. Oh yeah, and all this so you can strap on a pair of skates and play hockey. It’s a good gig, it really is, but it doesn’t work out so nicely for all players. Take any of the names below and a slew of others, who were the victims of unrelenting criticism for failing to live up to a big money contract that any one of us would have signed in a heartbeat. Is that worth millions? Some of these athletes have even been subject to harassment for not playing to a certain standard. It’s silly stuff, but that’s the world of sports.

A lot of these players are in fact quite talented and capable of upgrading a variety of teams around the league. The problem, however, is they become phased out of the league on account of a lack of teams able to absorb their contract under the salary cap. Many of them end up plying their trade overseas and tarnish their reputation in the NHL. It happens nearly every summer these days, as general managers outbid each other and overpay for talent. It weakens the team and places unfair expectations on the player, and that helps nobody.

With that in mind, here is the list of the worst free agent signings in NHL history. It’s a cautionary tale, one that remains relevant year after year.

12. Bobby Holik to the New York Rangers

Via bleacherreport.com

Via bleacherreport.com

Five years for $45 million. That’s what the New York Rangers awarded Bobby Holik as a free agent after putting up a few 60-point seasons with the New Jersey Devils. He played in New York for two years before being bought out and moving on to the Atlanta Thrashers. Holik, to his credit, performed to his career average in his second season, producing 56 points, but it proved to be too little for Glen Sather and the Rangers. While Holik will be forever criticized for his short stint in New York, it’s Sather who should be chastised for his poor decision making.

11. Stephen Weiss to the Detroit Red Wings

Rick Osentoski-USA TODAY Sports

Rick Osentoski-USA TODAY Sports

Stephen Weiss was once a coveted target on July 1, representing one of the better options at center in what was a limited free agent pool in the summer of 2013. The Detroit Red Wings locked him up for five years with a $4.9 million cap hit following a rough campaign in which he produced four points in 17 games and sustained a lingering wrist injury. That didn’t deter the Red Wings, though, who dished out considerable dough to lock up his services. He notched two goals and two assists in his first season… in 24 games. He didn’t fare much better last season, putting up a measly 25 points in 52 games.

10. Cristobal Huet to the Chicago Blackhawks

Cristobal Huet

Signing with the Chicago Blackhawks as a free agent goaltender was the worst thing to ever happen to Cristobal Huet’s career. After putting up above average save percentages with the Montreal Canadiens and Washington Capitals—albeit in 13 games—Huet’s value took a hit after registering a .909 save percentage in his first season with the Blackhawks after signing a monstrous four-year, $22.5 million contract. His second campaign was disastrous, putting up an abysmal .895 save percentage in 48 games, losing his starting role in the process. He now plays in the Swiss-A, where he has been recording stellar statistics. An NHL comeback is unlikely at this point, though.

9. Wade Redden to the New York Rangers

Wade Redden

Wade Redden endured a successful 11-year career with the Ottawa Senators, once putting up a career-high 50 points in a shortened campaign. Once he was eligible to be signed as a free agent, the New York Rangers swooped in with a gaudy six-year, $39 million contract to lure him away from Canada’s capital. But Redden suffered a considerable setback in his first season with the Rangers, putting up a mere 26 points in 81 games. His second season went even worse and marked his unofficial derailment as an NHL player after he produced 14 points in 75 games. He spent the next two seasons in the AHL before having brief stints with the St. Louis Blues and the Boston Bruins.

8. Jeff Finger to the Toronto Maple Leafs

Vesa Toskala, Jeff Finger

Jeff Finger was supposed to be one of Cliff Fletcher’s marquee signings in the summer of 2008, despite the defenceman’s relatively unknown status. Fletcher locked him up for four years at $14 million, a hefty price tag for a player who was supposed to be a defensive defenseman. Finger played for the Toronto Maple Leafs for a season and a half before being sent to the minors as one of the highest paid players in the AHL. It was one of Fletcher’s final moments as general manager, representing a giant Finger to the face of his former employer. Moral of the story: Don’t overpay defensive defensemen, ever.

7. Brad Richards to the New York Rangers

Sergei Belski-USA TODAY Sports

Sergei Belski-USA TODAY Sports

Brad Richards was once a premier player in the league before he signed a nine-year, $60 million contract with the New York Rangers. General manager Glen Sather thought he had landed a sure-fire superstar for the next decade but instead received three years of underwhelming performances. Signing a 31-year-old until he was 40 years old was never a good idea to begin with, but to be fair to the Rangers, few had foreseen such a drop-off for the centerman. It’s not to suggest Richards performed poorly, 66 points in his first season is certainly decent, but he simply couldn’t justify the behemoth contract and it resulted in him being bought out three years later. It worked out, too, considering he won his second Stanley Cup with the Chicago Blackhawks this season.

6. Sheldon Souray to the Edmonton Oilers

Sheldon Souray

Sheldon Souray was supposed to shore up the Edmonton Oilers’ blueline after finding success with the Montreal Canadiens, coming off a 26-goal, 64-point campaign. His first season was cut short due to injury, and his production staggered to three goals and 10 points. He followed that up with an impressive 53-point campaign but the success was short-lived as he sustained another injury and had his production halted once more. From there, he spent time in the AHL putting up underwhelming numbers before having two brief stints in the NHL with the Dallas Stars and Anaheim Ducks, never successfully finding his footing.

5. Scott Gomez to the New York Rangers

Scott Gomez

Scott Gomez experienced one of the steepest declines in NHL history. It all started when he signed a mammoth seven-year, $51.5 million contract with the New York Rangers. He started off on the right foot, putting up 70 points, but followed that up with two 50-point campaigns before having his production halved and being passed around the league. The burden of his contract ended up falling on the Montreal Canadiens, who acquired the Alaskan via trade. One of the worst contracts in NHL history was eventually terminated by the Canadiens, who opted to buy out Gomez. So just how low did Gomez sink? Well, someone took upon themselves to create the website www.didgomezscore.com

4. Nathan Horton to the Columbus Blue Jackets

Eric Bolte-USA TODAY Sports

Eric Bolte-USA TODAY Sports

Nathan Horton was a productive power forward in the NHL. The keyword there is “was.” That’s because Horton suffered a shoulder injury that was the beginning of the end of his hockey career. The Columbus Blue Jackets, however, obviously thought he’d recover after awarding him a seven-year, $37.1 million contract as a free agent. Suffice to say, Horton played a grand total of 35 games before being shut down indefinitely, with his career still very much in jeopardy. The Blue Jackets solved that problem by trading him away for an even worse contract in David Clarkson. Never invest in a broken toy.

3. Ryane Clowe to the New Jersey Devils

Kim Klement-USA TODAY Sports

Kim Klement-USA TODAY Sports

Signing Ryane Clowe to a five-year contract that pays him $4.85 million annually will go down as one of the biggest mistakes in New Jersey Devils history. With his career in jeopardy following his ongoing bout with concussion symptoms, it’s likely the power forward may never player another game in the NHL. He amassed a total of eight goals and 30 points in 56 career games with the Devils, so it’s fair to say they far from got their money’s worth. The contract is especially bad because the signs were there the season heading into free agency, in which he collected three goals and 19 points in an injury plagued campaign.

2. Ville Leino to the Buffalo Sabres

Timothy T. Ludwig-USA TODAY Sports

Timothy T. Ludwig-USA TODAY Sports

Oof. Ville Leino turned out to be one of the biggest misfires in NHL history. The Buffalo Sabres locked up his services for six years at $27 million. The then 27-year-old was coming off a career-high 53 points and a productive playoff run the season prior with 21 points in 19 games. If the Sabres had done their homework, however, they would have discovered that Leino was never a consistent point producer, and at 27 years old the chances of him sustaining his sudden success were slim. He had played three seasons with Buffalo, putting up a high of 25 points before being bought out.

1. David Clarkson to the Toronto Maple Leafs

Tom Szczerbowski-USA TODAY Sports

Tom Szczerbowski-USA TODAY Sports

Oh, David Clarkson. This is a tragic case of a player being overvalued and hyped considerably in the media for his character and willingness to win. He was primed for failure in Toronto the moment he signed on the dotted line for a seven-year, $36.75 million contract. The problem with Clarkson wasn’t so much his value to the team, he’s a decent third liner, but he’s paid like a top-six forward and there was no way he’d ever live up those expectations. Like Leino, he enjoyed a productive campaign that had some general managers thinking he could pot 25 to 30 goals. Not the case.

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