Every trade made in the National Hockey League is a gamble. General Managers roll the metaphorical dice and see if they can parlay their currently held assets for a net gain in terms of talent and cap room. Sometimes, a GM’s actions are forced because of a player demanded trade or maybe a no-trade clause limits the potential destinations. Many factors must be considered when assessing a player’s trade value and they must be weighed according to the expectation of fans, who judge every move with the highest degree of scrutiny.

Starting with the legendary Lester Patrick when the Rangers were founded in 1926, 11 men have had the coveted, but pressure filled job of deciding who gets to pull on the blue sweater. Each has had to deal with a different set of circumstances as relations between players, ownership, and coaching staffs have changed over time. Modern GMs deal with a far higher amount of daily analysis when compared to their counterparts from the Original Six era. Despite the change in eras, the end goal remains the same, as Jeff Gorton looks to build the squad that can lift the same Stanley Cup hoisted by Mark Messier.

It has been 22 years since Messier’s guarantee and Rangers fans are growing restless as Henrik Lundqvist enters the twilight of his career. Success has always been difficult to achieve in the NHL, and building a cohesive team is a highly publicized highwire act. This article will cover the most unfortunate trade acquisitions in Rangers history, where Rangers GMs put their teams in a worse position than if they had held pat.

15. Mike Keane to Dallas

via patrickfallonphoto.com

via patrickfallonphoto.com

When Mike Keane was shipped to Dallas along with Brian Skrudland and a sixth round choice that eventually became Pavel Patera, it was a necessary shakeup because Keane’s production had taken a serious dive. The Rangers received Bob Errey, Todd Harvey, and a pick used to select Boyd Kane. Keane’s production took an immediate increase and he played well enough to earn Selke consideration in two of the next three seasons. Meanwhile, Errey and Harvey only played a total of 80 games for the Rangers, while Kane never managed to make an appearance with the club. Keane was a key member of the Stars back to back Stanley Cup runs that ended with him lifting the Cup in 1999. By every measure, the Rangers were big losers in this deal.

14. Ed Olczyk to Winnipeg

via sortingbyteams.wordpress.com

via sortingbyteams.wordpress.com

Eddie Olczyk’s tenure in New York was an overall success because of the end result of the Rangers lifting the Stanley Cup. The Rangers gave up Tie Domi in order to acquire Olczyk only to have him miss the majority of the 1993-94 season with a thumb injury. Olczyk’s production returned to career average numbers after being dealt back to the Jets in exchange for a fifth round NHL draft selection that would eventually be used on Alexei Vasilev. Vasiliev was a defenseman who made only a single appearance in the NHL for the Rangers, before returning to play in the KHL for Lokomotiv Yaroslavl. Olczyk’s contribution to that Stanley Cup winning team wasn’t enormous, so the Rangers missing out on the prime years of Tie Domi was a high price to pay.

13. Tony Amonte to the Blackhawks

via picclick.ca

via picclick.ca

Tony Amonte played his first three NHL seasons with the Rangers starting in 1991. After finishing second in Calder Trophy voting his rookie year, his production increased in his second season before heading south in year three. The Rangers panicked and dealt the struggling American All-Star with just seven games remaining in the 1993-94 regular season. They received Brian Noonan and Stephane Matteau in exchange, who both saw their names etched on the Cup at the end of the year. However, Amonte went on to become a consistently productive star for the Blackhawks, leading to five career All-Star game appearances. He currently holds the ninth highest point total of all-time for an American player. Noonan and Matteau did not continue with the Rangers beyond the 1995-96 season.

12. John Vanbiesbrouck to Vancouver

via alchetron.com

via alchetron.com

The Rangers had a goaltender problem in the 1992-93 season. John Vanbiesbrouck was an aging 29-year-old veteran, who many thought had already played the best hockey of his career. Mike Richter was a 26-year-old goaltender that was poised to take the reins and the Rangers needed to make their move in the offseason. The Beezer was sent to Vancouver for future considerations that eventually became Doug Lidster who played a few seasons for New York. After being claimed by the Florida Panthers in the expansion draft, Vanbiesbrouck had a career Renaissance, returning to the Vezina winning form he displayed early as a Ranger. Vanbiesbrouck was a crucial part of the Panthers run to the Stanley Cup in 1995 where they were defeated by the Colorado Avalanche in four games.

11. Carl Hagelin to Anaheim

Reinhold Matay-USA TODAY Sports

Reinhold Matay-USA TODAY Sports

After being drafted by the Rangers in the sixth round of the 2007 Draft, Carl Hagelin took a while to make his first appearance for the team. His rookie season was good enough to earn him votes for the Calder Trophy and he has developed into a forward that excels in the defensive areas of the game. The Rangers found him surplus to their needs and Glen Sather dealt him along with second and sixth round picks to Anaheim for Emerson Etem and a 2nd round pick. After playing half a season in Anaheim, he was shipped to Pittsburgh, where he helped the Penguins win the Stanley Cup. Etem played only 19 games for the Rangers before being traded, while the pick used to select Ryan Gropp remains to be seen as a wise decision. Either way, Hagelin looks to have many years of NHL hockey ahead of him.

10. Alexei Kovalev to Montreal

via espn.com

via espn.com

Alexei Kovalev was selected with the 15th overall pick by the New York Rangers in the 1991 Entry Draft. The first player from the Soviet Union to be chosen in the first round, Kovalev was a dynamic player. He was on the 1994 Stanley Cup winning team before being traded to the Pittsburgh Penguins in a 1998 blockbuster deal that saw the Rangers acquire Petr Nedved among others. Kovalev enjoyed a few good seasons in Pittsburgh before returning to NYC in 2004 in another multi-player trade. Just over a year later, he was unceremoniously cast off to the Montreal Canadiens for Jozef Balej and a second round pick. Kovalev quickly returned to his prior form and managed to earn another All-Star appearance with Montreal, that saw him become the first ever Russian All-Star game captain.

9. Pascal Dupuis to Atlanta

Charles LeClaire-USA TODAY Sports

Charles LeClaire-USA TODAY Sports

Pascal Dupuis’ tenure in New York was a short term engagement and only lasted 18 days. During his six games with the Rangers, Dupuis managed only a single goal for his lone point in a blue sweater. Less than three weeks after arriving in a trade for Adam Hall, Dupuis was sent packing to Atlanta along with a third round pick in the 2007 Draft that was eventually traded to Pittsburgh in exchange for Alex Bourret. Bourret bounced around many minor league clubs, but was never able to make an appearance in the NHL. Meanwhile, Pascal Dupuis would eventually go one to play a secondary role on the Pittsburgh Penguins as they made their way to a Stanley Cup Final victory in 2009 and remains a beloved figure in the Steel City.

8. Matt Cullen to Carolina

Kim Klement-USA TODAY Sports

Kim Klement-USA TODAY Sports

Following the lockout of the 2004-05 season, Matt Cullen was fresh off a 49 point season and signed a free agency deal with the Rangers. Cullen played in 80 games and took a hit to his production, but was still a fairly competent option at center. The Rangers looked at their balance sheet and decided he was expendable, so they moved him to Carolina in exchange for Andrew Hutchinson, Joe Barnes and a third round pick that eventually became Evgeni Grachev. Hutchinson and Barnes never appeared in a game for the Rangers, while Grachev managed only eight appearances for the club. Cullen’s production immediately returned to where it was in his previous stint with the Hurricanes and he continues his NHL career to this day.

7. Keith Yandle to Florida

Vincent Carchietta-USA TODAY Sports

Vincent Carchietta-USA TODAY Sports

This move may be a little premature to judge, but the trade of Keith Yandle to Florida is already showing signs of being a mistake. Yandle’s production was underappreciated as he helped the Rangers to the Stanley Cup Finals after being acquired in March 2015. His two goals and nine assists in the playoffs were enormous from a defenseman, but his lone goal during the next season’s playoff campaign wasn’t enough to keep him in town. The Rangers received a sixth round pick in 2016 and a fourth in 2017 from the Panthers in exchange for the veteran blueliner, who was slated to be a free agent, though we’re arguing the Rangers should’ve beared down and signed the star defender. He is currently the most productive defenseman on the Panthers. While it remains to be seen what the Rangers actually gained from this trade, it is unlikely it will meet the performances Yandle has routinely shown he’s capable of delivering.

6. Trading Brian Leetch…Twice

via nydailynews.com

via nydailynews.com

Brian Leetch is undeniably one of the greatest Rangers players of all-time. His teammate, Mark Messier, considers him to be the greatest. Leetch was selected with the ninth pick in the 1986 Entry Draft and played the next 17 seasons in a blue sweater. He won the Stanley Cup, two Norris Trophies, the Calder Trophy, and the Conn Smythe Trophy. His quiet determination was the model of what all hockey fans respect and love in a captain. In an effort to dump the salaries of veterans, the New York Rangers traded Leetch to Edmonton in 2003 for Jussi Markkanen and a fourth round pick. He returned to New York as a free agent the following season on a free agent deal only to be traded to Toronto for a series of inconsequential players. 2005 saw Leetch sign with the Boston Bruins, when he scored his 1,000th career point in a Bruins jersey.

5. Marc Savard to Calgary

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via pinterest.com

Marc Savard came into the NHL with burden that comes with having the last name of Savard. Success was expected even though Savard was taken in the fourth round by the Rangers. Two seasons into his career Savard had showed flashes, but didn’t look to be a superstar, so the Rangers shipped him to Calgary along with a first round pick for Jan Hlavac, Jamie Lundmark, and a pick that became Craig Anderson. Savard continued to grow and mature in Calgary, eventually becoming an All-Star caliber player. Hlavac and Lundmark were both middling players during their tenures with the Rangers. Anderson never played for the Rangers, but did managed to find NHL success nearly a decade later with the Avalanche and Senators.

4. Eddie Shack to Toronto

via markoshockeyautos.blogspot.ca

via markoshockeyautos.blogspot.ca

After being developed in the Rangers farm system, Eddie Shack played two seasons for them as a wily left winger. In November 1960, they sent him to the Maple Leafs in exchange for Pat Hannigan and Johnny Wilson. Wilson and Hannigan combined for a total of 82 points during their respective tenures with the Rangers. While Shack was often criticized for his lack of goalscoring, he managed to find other ways to contribute as an agitator. He played a vital role in the four Stanley Cup titles that the Leafs won the 1960s. When he finally managed to find his scoring touch, he was honored with a folk song “Clear the Track, Here Comes Shack.” The song would eventually reach #1 on the Canadian pop charts.

3. Bob Crawford, Kelly Miller and Mike Ridley to Washington

via ussianmachineneverbreaks.com

via ussianmachineneverbreaks.com

In a move that summarized the brief, unhappy arrangement between Phil Esposito and the New York Rangers, the team legend sent Bob Crawford, Kelly Miller and Mike Ridley to the Washington Capitals in exchange for a second round pick and Bob Crawford. Carpenter, Miller, and Ridley would all go on to become NHL veterans each playing at least 12 seasons, though Carpenter would only spend 28 games with the Rangers. Bob Crawford would play 14 games for the Rangers before playing overseas. Following the departure of Esposito from the general manager position with the Rangers, the club was left to devise a draft strategy in 1989 without a top executive. They used the pick to draft enforcer Jason Prosofsky, who never managed a single NHL appearance in his hockey career, making this one of the most lopsided trades in Rangers history.

2. Rick Middleton for Ken Hodge

via hockeyautographs.ca

via hockeyautographs.ca

In 1976, Rick Middleton was showing signs of being a solid right winger for the New York Rangers, finishing his second NHL season with 50 points. Ken Hodge was showing obvious signs of decline after the age of 30 with the Boston Bruins, after seeing his production drop in consecutive seasons just prior to being dealt to the Rangers for Middleton. At opposite ends of their respective careers, they performed exactly as you’d expect, with Middleton continuing to improve, while Hodge managed to cobble together two more NHL seasons, before retiring at the age of 33. Middleton would go on to earn three All-Star game appearances and won the Lady Byng Trophy in 1981-82. On the heels of deals like this, Rangers GM John Ferguson Sr. was fired in 1978.

1. Phil Esposito for Brad Park and Jean Ratelle

via alchetron.com

via alchetron.com

Looking for a figure to build their team around in 1975, the New York Rangers looked north to their rivals the Boston Bruins. They found their man in Phil Esposito, the hardlined center, who wouldn’t sacrifice playing time despite his advancing age. In order to acquire the 33-year-old Esposito and Carol Vadnais, the Rangers sent Jean Ratelle, Brad Park, and Joe Zanuzzi. Park was considered one of the best defensemen in the league at the time and would continue his All-Star caliber play. Vadnais was an average defenseman, but Ratelle would continue to be a skilled center for the Bruins for six seasons, while Esposito never performed to the level of his days with the Bruins. The Rangers would eventually hire Esposito as a GM, where he earned the nickname Trader Phil.

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