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New York Rangers: Top 5 Worst Free Agent Signings Since 2010

By Justin Starr |
Dec 15, 2013; New York, NY, USA; New York Rangers center Brad Richards (19) fights for control of the puck with Calgary Flames defenseman Ladislav Smid (3) during the second period at Madison Square Garden. Mandatory Credit: Adam Hunger-USA TODAY Sports
Dec 15, 2013; New York, NY, USA; New York Rangers center Brad Richards (19) fights for control of the puck with Calgary Flames defenseman Ladislav Smid (3) during the second period at Madison Square Garden. Mandatory Credit: Adam Hunger-USA TODAY Sports
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Mandatory Credit: Brad Penner-USA TODAY Sports
Mandatory Credit: Brad Penner-USA TODAY Sports /

Every off-season, the teams in the National Hockey League look to retool and improve. They attempt to find the missing pieces that have been refraining them from lifting the Stanley Cup in June. The New York Rangers are known for going out and signing the highly touted free agent every summer. This list is composed of the top 5 worst Rangers free agent signings since 2010…

The New York Rangers are known throughout the league as one of those teams that always looks for the “shiny new toy”.

While Glen Sather was the general manager of the team, he had signed some players to some pretty large contracts. Names such as Marian Gaborik, Chris Drury, Scott Gomez, and Brendan Shanahan are just some of the examples of the Rangers signing the “shiny and new offseason toy”.

Glen Sather has found a way out of these rather large contracts most of the time and even turned one into the Rangers current captain, Ryan McDonagh (Thanks, Bob Gainey!). It seems as if the Rangers front office has somewhat learned their lesson. They haven’t signed a free agent to a large contract in a few years.  This is a list of the five worst Rangers free agent signings since 2010 in no particular order…

May 4, 2017; New York, NY, USA; New York Rangers left wing Tanner Glass (15) leaves the ice after a fight against the Ottawa Senators during the third period in game four of the second round of the 2017 Stanley Cup Playoffs at Madison Square Garden. Mandatory Credit: Adam Hunger-USA TODAY Sports
May 4, 2017; New York, NY, USA; New York Rangers left wing Tanner Glass (15) leaves the ice after a fight against the Ottawa Senators during the third period in game four of the second round of the 2017 Stanley Cup Playoffs at Madison Square Garden. Mandatory Credit: Adam Hunger-USA TODAY Sports /

Tanner Glass –

It is on the record that I am not a Tanner Glass fan, I never was and never will be. The New York Rangers and Tanner Glass came to terms on a three-year, $4.35 million contract on July 1, 2014. Tanner Glass plugged into the Rangers 4th line for 134 games throughout the three-year contract. He contributed six goals and nine assists during his tenure with the Rangers. He also kept younger, more talented players sitting in the press box.

Glass left his biggest impact during his Rangers’ tenure during the first round battle last season against the Montreal Canadiens. The Rangers desire to have a “tough” guy in their lineup brought them together with Tanner Glass. The $4.35 million could have been used elsewhere in 2014 but it’s in the past now. The three-year contract just came to an end this season and Tanner Glass is set to become an unrestricted free agent once more. It is time for Glass and the Rangers to go their separate ways.

Apr 9, 2016; New York, NY, USA; New York Rangers defenseman Dan Boyle (22) clears the puck in front of Detroit Red Wings center Dylan Larkin (71) during the third period at Madison Square Garden. The Rangers defeated the Red Wings 3-2. Mandatory Credit: Adam Hunger-USA TODAY Sports
Apr 9, 2016; New York, NY, USA; New York Rangers defenseman Dan Boyle (22) clears the puck in front of Detroit Red Wings center Dylan Larkin (71) during the third period at Madison Square Garden. The Rangers defeated the Red Wings 3-2. Mandatory Credit: Adam Hunger-USA TODAY Sports /

Dan Boyle –

Old man Boyle makes the list of the top 5 worst free agent signings since 2010. Dan Boyle signed a two-year, $9 million contract with the New York Rangers on July 1, 2014. The New York Rangers didn’t bring in the Dan Boyle in his prime playing for the San Jose Sharks. They signed the 38-year-old, Dan Boyle who probably should’ve hung up the skates after his tenure with the Sharks.

During his two seasons with the Rangers, Boyle played in 139 games and scored 19 goals and tallied 25 assists as well. Boyle hung up the skates after his contract with the Rangers ended. It’s interesting to think about who else the Rangers could’ve signed that off-season. The Rangers could’ve had a little over $13 million to play with if they hadn’t signed Boyle and Glass that summer.

Jun 3, 2014; Los Angeles, CA, USA; New York Rangers general manager Glen Sather during media day before game one of the 2014 Stanley Cup Final against the Los Angeles Kings at Staples Center. Mandatory Credit: Kirby Lee-USA TODAY Sports
Jun 3, 2014; Los Angeles, CA, USA; New York Rangers general manager Glen Sather during media day before game one of the 2014 Stanley Cup Final against the Los Angeles Kings at Staples Center. Mandatory Credit: Kirby Lee-USA TODAY Sports /

Jeff Woywitka –

Here is a name that Ranger fans thought they’d never hear again or perhaps never even knew! Jeff Woywitka and the Rangers came to terms on a one-year contract on August 16, 2011. This contract was more of a head shaker than anything else. Woywitka only suited up for the Rangers for 27 games during the 2011-2012 season.

Woywitka contributed a fun last name to say, one goal and five assists during his short stay in New York. The former first round pick never turned into anything spectacular during his NHL career. Woywitka could never get settled in the NHL and his career in the NHL was ended at the ripe age of 28. Can anyone recall what number Jeff Woywitka wore for the Rangers without googling it?

Apr 10, 2014; Saint Paul, MN, USA; St. Louis Blues left wing Alexander Steen (20) confronts Minnesota Wild left wing Mike Rupp (27) after a hit on right wing T.J. Oshie (74) in the second period at Xcel Energy Center. Mandatory Credit: Brad Rempel-USA TODAY Sports
Apr 10, 2014; Saint Paul, MN, USA; St. Louis Blues left wing Alexander Steen (20) confronts Minnesota Wild left wing Mike Rupp (27) after a hit on right wing T.J. Oshie (74) in the second period at Xcel Energy Center. Mandatory Credit: Brad Rempel-USA TODAY Sports /

Mike Rupp –

Mike Rupp was another classic case of the New York Rangers desperately wanting to add some toughness to their bottom six. The Rangers and Mike Rupp agreed to a three-year, $4.5 million contract on July 1, 2011. Rupp played 68 games for the New York Rangers and added four goals, one assist and 109 penalty minutes.

Rupp’s highlight as a Ranger came on January 2, 2012, when he scored two goals for the Rangers during the Winter Classic against the Philadelphia Flyers. Rupp gave the Flyer bench a “Jagr Salute” after his first goal.

Rupp went on to play two more seasons after his time with the Rangers came to an end. The wonders of who else the Rangers could’ve used that $4.5 million will always be a thought. Was the “Jagr Salute” worth $4.5 million?

Dec 15, 2013; New York, NY, USA; New York Rangers center Brad Richards (19) fights for control of the puck with Calgary Flames defenseman Ladislav Smid (3) during the second period at Madison Square Garden. Mandatory Credit: Adam Hunger-USA TODAY Sports
Dec 15, 2013; New York, NY, USA; New York Rangers center Brad Richards (19) fights for control of the puck with Calgary Flames defenseman Ladislav Smid (3) during the second period at Madison Square Garden. Mandatory Credit: Adam Hunger-USA TODAY Sports /

Brad Richards –

Now I want to be clear and say that I enjoyed what Brad Richards did for the New York Rangers. What I didn’t like was the size of his contract. The Rangers tried to get Richards from the Dallas Stars at the trade deadline in 2011 but the asking price was too high. The Rangers decided to wait until the summer to sign their “shiny new toy”.

On July 2, 2011, Richards signed a nine-year, $58.5 million contract with the Rangers. This contract would’ve come to an end when Richards would be 40-years-old. The Rangers should’ve signed Richards to a shorter contract and maybe things wouldn’t have ended the way they did.

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Richards scored 56 goals and added 95 assists during his stint with the Rangers. He helped the team reach the Stanley Cup final in 2014 and added many memories along the journey. The former third round pick was eventually bought out of his contract the summer after that run to the Stanley Cup in 2014. This contract was a typical “Rangers contact” of old such as the Drury, Gomez and Gaborik contracts. Let’s hope the Rangers front office doesn’t make a mistake like this contract this summer.

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