OTTAWA, ON – JANUARY 21: David Clarkson #71 of the Toronto Maple Leafs looks on during a game against the Ottawa Senators at Canadian Tire Centre on January 21, 2015 in Ottawa, Ontario, Canada. (Photo by Jana Chytilova/Freestyle Photography/Getty Images) *** Local Caption *** David Clarkson

You are not always going to hit a home run when looking at free agency. When looking back at some contracts over the last decade, there have been some that completely flopped. Today, we will rank them and discuss what made the money vanish quicker than ever. 

10. Vadim Shipachyov (2 yr/$9 Million)

LAS VEGAS, NV – OCTOBER 17: Vadim Shipachyov #87 of the Vegas Golden Knights skates with the puck ahead of Jordan Nolan #17 of the Buffalo Sabres in the second period of their game at T-Mobile Arena on October 17, 2017 in Las Vegas, Nevada. The Golden Knights won 5-4 in overtime. (Photo by Ethan Miller/Getty Images)

Vadim Shipachyov was expected to be a solid second-line center for the Vegas Golden Knights, a brand-new expansion team ready to stand in the NHL. In 2017, Shipachyov signed a two-year, $9 million deal with the Golden Knights, and there was excitement. However, things turned south quickly. After three games, Vegas sent him down to the AHL, but he refused to report. 

He would be suspended by the team and returned to Russia, where he voluntarily retired from the National Hockey League. In three games, he managed to score a goal. He would be higher on the list, but the fact that the Golden Knights did not have to take on so much money means that he would be right at 10. 

9. Karl Alzner (5 years/ $23.125 Million)

MONTREAL, QC – FEBRUARY 25: Karl Alzner #27 of the Montreal Canadiens defends the puck from Tyler Toffoli #73 of the Vancouver Canucks during the first period at the Bell Centre on February 25, 2020 in Montreal, Canada. (Photo by Minas Panagiotakis/Getty Images)

Defenseman Karl Alzner was the fifth overall pick in the 2007 NHL Entry draft. He played nine years for the Washington Capitals before inking a five-year contract worth under $5 million per season with the Montreal Canadiens. He was not known as a point producer, as his career high was 21 before signing the deal. 

In 95 games over the course of three seasons, Alzner finished with 95 games played and 13 points. He would be demoted to the AHL and retired after the 2019-2020 season. 

8. Andrew Ladd (7 years/$38.5 Million)

UNIONDALE, NEW YORK – MARCH 07: Andrew Ladd #16 of the New York Islanders skates against the Carolina Hurricanes at NYCB Live’s Nassau Coliseum on March 07, 2020 in Uniondale, New York. (Photo by Bruce Bennett/Getty Images)

By the time the 2016 offseason began, we already knew what left winger Andrew Ladd was as a player. He was entering his age-31 season and consistently was scoring 20+ goals a season. However, the Islanders decided to pay more than $5 million per year on a seven-year contract and that did not work out great. 

In 181 games over four years, he finished with 72 points and was traded to the Arizona Coyotes in a salary dump where the Islanders had to sweeten the pot with two second-round picks and a third-round pick for the salary cap relief. 

7. Loui Eriksson (6 years/$36 Million)

VANCOUVER, BC – JANUARY 18: Loui Eriksson #21 of the Vancouver Canucks celebrates after scoring a goal against the San Jose Sharks in NHL action on January, 18, 2020 at Rogers Arena in Vancouver, British Columbia, Canada. (Photo by Rich Lam/Getty Images)

Loui Eriksson showcased his skills in his first 10 seasons in the NHL with Dallas and Boston before the 2016 offseason. He was able to use a 63-point season to wow the decision-makers for the Vancouver Canucks to ink him to a six-year deal worth $6 million per season. 

However, he has struggled to find his footing north of the border as he could only be in the third and fourth lines consistently. He would play five seasons with the Canucks before his 90 points with the franchise was shipped to Arizona. He would play one season with the Coyotes, but the money was not worth signing him for a large deal.  

6. Brent Seabrook (8 years/$55 Million)

CHICAGO, ILLINOIS – SEPTEMBER 25: Brent Seabrook #7 of the Chicago Blackhawks waits for a face-off against the Washington Capitals during a preseason game at the United Center on September 25, 2019 in Chicago, Illinois. (Photo by Jonathan Daniel/Getty Images)

Brent Seabrook embodies paying players for what they have done more than what they will do for your team. The Chicago Blackhawks re-signed him before the 2015 season when he got eight years for a little under $7 million per year. Seabrook played five seasons under the contract before retiring and finished with 146 points but was nowhere near the player that helped the team win three Stanley Cups earlier in his career.  

5. David Clarkson (7 years/$36.75 Million)

NEWARK, NJ – JANUARY 28: David Clarkson #71 of the Toronto Maple Leafs skates against the New Jersey Devils at the Prudential Center on January 28, 2015 in Newark, New Jersey. The Devils defeated the Maple Leafs 2-1 in the shootout. (Photo by Bruce Bennett/Getty Images)

David Clarkson barely makes this list regarding the time element, but the Maple Leafs fans will surely remember this signing. He played two solid seasons during a mediocre career heading into the 2013 offseason. He would head north and leave the Devils to sign a seven-year deal with the Maple Leafs. However, this was not a long stay, as he was quickly traded away in less than two seasons. 

4. Leo Komarov (4 years/$12 Million)

UNIONDALE, NEW YORK – JUNE 17: Leo Komarov #47 of the New York Islanders gets tripped up against the Tampa Bay Lightning during the second period in Game Three of the Stanley Cup Semifinals during the 2021 Stanley Cup Playoffs at Nassau Coliseum on June 17, 2021 in Uniondale, New York. (Photo by Bruce Bennett/Getty Images)

While this deal did not hurt the salary cap as much as other contracts on this list, it is important to highlight it here. The Islanders were in the market for a center, and during the 2018 offseason, they signed Komarov to a four-year contract. He did not produce anywhere near the 122 points he did during his five years with Toronto. Instead, he would appear in 164 games during the contract and record 48 points. $250,000 per point in the contract is not the ideal situation.  

3. Nathan Horton (7 years/$37.1 Million)

GLENDALE, AZ – JANUARY 02: Nathan Horton #8 of the Columbus Blue Jackets during the NHL game against the Phoenix Coyotes at Jobing.com Arena on January 2, 2014 in Glendale, Arizona. The Blue Jackets defeated the Coyotes 2-0. (Photo by Christian Petersen/Getty Images)

Nathan Horton had some issues staying on the ice before the 2013 offseason as the two years prior, he only appeared in 89 games for the Bruins. However, that did not stop the Columbus Blue Jackets from backing up the Brinks truck for Horton. He would only play one season of the contract before injuries kept him sidelined. He would be part of the David Clarkson trade, and the reason this deal is this high is because the Blue Jackets did not insure the contract. That meant Columbus still had to pay him despite being hurt. 

2. Mikkel Bodker (4 years/$16 Million)

SAN JOSE, CA – APRIL 16: Mikkel Boedker #89 of the San Jose Sharks skates up ice with control of the puck pursued by Ryan Getzlaf #15 of the Anaheim Ducks during the second period in Game Three of the Western Conference First Round during the 2018 NHL Stanley Cup Playoffs at SAP Center on April 16, 2018 in San Jose, California. (Photo by Thearon W. Henderson/Getty Images)

Mikkel Bodker showed promise as he produced well throughout his career. During the 2016 offseason, the San Jose Sharks decided to ink him to a four-year, $16 million contract as he emerged as a solid player. However, plans went awry, as he only played two seasons with the Sharks before being shipped to Ottawa in a trade. His 25 goals were not what many expected, and it was not much better as he would only score nine goals in his two seasons with Ottawa.

1. Ville Leino (6 years/$27 Million)

UNIONDALE, NY – FEBRUARY 04: Ville Leino #23 of the Buffalo Sabres skates against the New York Islanders at the Nassau Veterans Memorial Coliseum on February 4, 2012 in Uniondale, New York. The Sabres defeated the Islanders 4-3 in the shootout. (Photo by Bruce Bennett/Getty Images)

Technically, this deal was not signed in the previous decade but ran through a significant part of the time and cannot be left off this list. Ville Leino signed a six-year, $27 million deal with the Buffalo Sabres. He only managed to record 25 points in his first season with the team and appeared in eight games the following season during a lockout-shortened season.

He would be bought out after the 2013-14 season and was paid more than $1.2 million for six seasons as part of the buyout.  



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