A couple of days ago we ranked the ten-best trades that General Managers Glen Sather and Jeff Gorton made during the 2010s. It’s now time to create its opposite list. While the Rangers’ pursuits on the trade market the last decade have been largely positive, there have been some stinkers sprinkled in as well.

Here are the criteria considered when picking and ranking the ten-worst deals.

Immediate Face Value Appraisal

I’m heavily analyzing the trade’s value at the time it actually happened. We’re evaluating at the time of the trade while pretending we can’t see the future. If the Rangers trade Filip Chytil for a seventh-round pick then that’s horrible value. I’m not going to consider it a win if they then take a good player with that pick.

Hindsight Analysis

That being said, I’m still going to considering the actual outcomes of the trades. So yes, blowing draft picks acquired in a trade will be hurt its valuation.

Impact on Team’s Success

Trading is a means to an end towards accomplishing greater goals as an organization. We’re not just evaluating the value of a deal itself, but also its contribution to the team’s intended accomplishments. So, we’re going to evaluate the greater context of a deal. What was the team’s situation, and did that kind of trade make sense at the time?

Butterfly Effect... To a Degree

The greater context of deals will be considered beyond the value seen in the trade itself. Did a move restrict the team’s cap space or force a separate traded? Great, that earns bonus points. What we’re not going to do is assign meaningful value to a third-round pick that was part of a chain of events that resulted in Kevin Shattenkirk being bought out four trades and eight years later. The future consequences of a trade have to be immediate and obvious.

10. Sixth-Round Pick (2012) to Nashville for Peter Ceresnak (2011)

Date: June 25th, 2011

Technically, the trade was a swap of draft picks. The Rangers had previously traded their 2011 sixth-round pick to San Jose for Jody Shelley (another contender for this list, but I digress). As the sixth-round occurred in Minnesota, the Rangers moved back into the mix by swapping their 2012 pick to Nashville for the 172nd overall pick.

The Rangers then immediately used the pick to draft defenseman Peter Ceresnak. The Slovakian defenseman was immobile, awkward with the puck, and lacked any offensive ability. He played in the OHL the following two seasons and produced just two 27 points in 117 games. The Rangers didn’t bother to offer him an entry-level contract, as it was painfully obvious he would not be good enough even for the AHL.

Bad draft picks happen, and especially in the later rounds. The reason this swap of sixth-round picks makes the list is that the Rangers had to go out of their way to make this happen. It’s not just that the Rangers made a bad selection, but that the scouting department specifically flagged Ceresnak as so important that they should make a trade to acquire him.

Let’s give the Rangers a break, though. If one of the ten-worst trades you made over the span of a decade centered around wasting a sixth-round pick, then you’re doing pretty well.

9. Sixth-Round Pick, Ben Ferriero to Minnesota for Justin Falk

Date: June 30th, 2013

Speaking of wasted sixth-round picks.

The Rangers’ defense was looking very good for the 2013-2014 season. Only minor maintenance was needed, as seventh defenseman Steve Eminger left the team, leaving a depth spot needing to be filled.

The Rangers tried to address this by acquiring defenseman Justin Falk from the Minnesota Wild. Falk was a 25-year-old defenseman who, and stop me if you’ve heard this before, was immobile, handled the puck like a grenade, and has zero offensive ability, but was very tall (6’5).

Head Coach Alain Vigneault barely tried to hide his disapproval of Falk’s ability to play hockey. He played Falk only when forced to, and even then usually held him to under 12 minutes per night. After December, Vigneault literally did not insert Falk into the lineup again until the final game of the season, which was a meaningless game against Pittsburgh where the only objective was for nobody to get hurt.

In fact, the coaching staff was so unimpressed by Falk that the Rangers had to hit the trade market again just to add another extra defenseman the team could trust. In early March, a fifth-round pick was sent to Vancouver in return for Raphael Diaz, who was more than up for the task.

Given the team’s low stock of draft picks during this contending era, sacrificing two of them  just to find a competent press box defenseman isn’t something that could be shrugged off.

8. Third-Round Pick, Tim Kennedy to Florida for Bryan McCabe

Date: February 26th, 2011

A young Rangers team was fighting to make the playoffs. There were many issues, but a big one was the below-average power play. Michal Rozsival had been traded earlier in the season. Michael Del Zotto was having a massive sophomore slump. McCabe, a veteran defenseman, was brought in at the deadline to solve this issue.

The move didn’t really work. McCabe registered just two goals and four assists in 19 regular season games for the Rangers, though it should be pointed out that all six points were on the power play. Overall, McCabe just didn’t really bring much to the table. He was irrelevant at best at even strength. In his prime, McCabe was a dynamic offensive defenseman. At 35 years old, he was no longer anything close to that player.

This trade was bad not only because of McCabe, but because of the scenario. This was a team that didn’t clinch a playoff spot until the final day of the season. Its top-two forwards in Marian Gaborik and Vinny Prospal were dealing with injuries all season long. Nobody realistically expected them to go anywhere, and sure enough they were jettisoned from the playoffs after five games against a lethal Washington Capitals team.

If a rental doesn’t work out, then it doesn’t work out. But this wasn’t a season that called for the team to be buyers in the first place.

7.  Ryan Graves to Colorado for Chase Bigras

Date: February 26th, 2018

The 2018 trading deadline is an iconic moment in recent Rangers’ history, as the team publicly declared its intention to blow it all up and start over with a hard rebuild. During the chaos, a small bartering of AHL defensemen went under the radar.

The Rangers shipped 22-year-old defenseman Ryan Graves to Colorado in return for Chris Bigras. Graves, previously a fourth-round pick in 2013, had developed at a surprising rate in Hartford. He was a top defenseman and locker room leader. The decision to move on from him was a bit curious, and especially so given that he never earned a chance in the AHL while the team instead gave playing time to the likes of Steve Kampfer and Rob O’Gara, among others.

Bigras actually played pretty well in Hartford early into his tenure. His play gradually dropped off a bit until a serious leg injury put him on the shelf. The Rangers parted with him this past summer.

Graves, meanwhile, has quickly risen up the depth chart in Colorado. Though he started in the AHL, he earned his first NHL call-up late in December of 2018. He’s stuck since. This season, he has played very well for the Avalanche and has produced six goals and nine assists through 35 games. He’s a regular in the lineup for a Stanley Cup contender. The Rangers, meanwhile, continue to look for solutions on the left side of its defense.

The team does have a number of quality left-handed defense prospects, which lessens the blow a bit, but they sure could use a capable 24-year-old lefty on the NHL roster right now. One has to wonder why he was never given a chance.

6. Fifth-Round Pick to Chicago for John Scott

Date: February 27th, 2012

The trade itself shouldn’t require much analysis to convince you that it was a bad deal. The Rangers gave up a fifth-round pick for a goon with one goal and four assists through 140 career games. That’s a bad trade!

Following his acquisition, Scott played a total of six games in March, averaging just 5:33 of icetime, before Head Coach John Tortorella decided he had seen enough and sent Scott to the press box for good.

This trade sits sixth on this list because of the context surrounding it. First of all, why? Just, why? Even if you accept an old school mentality that a team needs a certain kind of pugilistic mentality to succeed, Scott was completely unnecessary. The Rangers already employed Brandon Prust, Mike Rupp, Stu Bickel, and Brandon Dubinsky. They lead the NHL in hits by a wide margin.

More importantly, the 2011-2012 Rangers were, at least in terms of its record, one of the top teams in the NHL. They finished first place in the Eastern Conference and just barely missed out on the Presidents’ Trophy. After years of wasting draft picks and prospects in deadline trades for teams going nowhere, now was finally the time where it actually made sense for the Rangers to splurge and add a piece for its first realistic Cup run in 15 years. How ironic that, of all years, this is the one where the team chose to sit on its hands. Except for acquiring Scott of course.

The Rangers were two games away from making the Stanley Cup Final. With margins so thin, would trading for a capable third liner instead have been the difference? It’s an uneasy question to contemplate in hindsight.

5. Lee Stempniak to Winnipeg for Carl Klingberg

Date: March 1st, 2015

The Rangers had a gem in Lee Stempniak. The Rangers somehow signed him as a free agent for only a $900K cap hit. He was a great two-way depth forward. He chipped in offense, he could kill penalties, and his puck possession metrics were fabulous.

For whatever reasons, Head Coach Alain Vigneault did not agree. Stempniak was often a healthy scratch, and when he did play he typically received far fewer minutes than he deserved. Nonetheless, Stempniak scored nine goals and added nine assists in 58 games despite averaging just 12:26 per night. Quality bottom-six production.

The Rangers apparently decided that Tanner Glass and newly acquired James Sheppard were better options on the wing. They unceremoniously shipped Stempniak to Winnipeg in return for Carl Klingberg.

Klingberg was a 24-year-old AHLer. He played 26 games for the Wolf Pack, and then gave away his rights after choosing to not give him a qualifying offer. He has since bounced around Europe.

Stempniak thrived after leaving the Rangers. He registered 10 points in 18 games for Winnipeg, then registered 91 points in the following two seasons for New Jersey and Boston.

In effect, the Rangers gave away Stempniak for free. Why? Who knows. They suffered some injuries in the playoffs, went to the Conference Final, and lost 2-0 at home to Tampa Bay in Game Seven. A couple of goals was the difference between the end of the season and a second-straight Stanley Cup Final appearance. Does that series end differently if Stempniak is there and receiving top-nine minutes? Maybe not.

But, also, maybe.

4. Carl Hagelin, 59th overall pick, 176th overall pick to Anaheim for Emerson Etem, 41st overall pick

Date: June 27th, 2015

The Rangers didn’t really have a choice but to trade a few players at the 2015 NHL Draft. They were under a major salary cap crunch, and a few players needed to be sacrificed. Hagelin, along with goaltender Cam Talbot, were the victims.

Trading Hagelin was probably the right move. He needed a new contract and was a year from unrestricted free agency. He was a good player, but expensive third liners aren’t typically conducive to building a competitive roster. Anaheim signed Hagelin to a four-year, $16M contract and then almost immediately regretted it. The Rangers were absolutely correct in not wanting to go anywhere near that.

It’s not that they traded Hagelin, but rather that they didn’t end up with anything of substance. Etem was a talented 23-year-old who put up big numbers in the AHL and showed flashes in the NHLL but just couldn’t stick. With the Rangers, he flopped. Etem tallied no goals and three assists in 19 games before being shipped off to Vancouver for a minor return. Etem’s acquisition looks horrible in hindsight and definitely plays a big role in why this trade ranks so high. At the time, it was understandable why the Rangers thought he might be worth a gamble.

Less excusable is their use of the 41st-overall pick. With numerous talented players available, the Rangers reached for WHL winger Ryan Gropp. Director of Player Development Gordie Clark told the media later in the day that they rated Gropp as the sixth-best forward in the entire draft.

Gropp has since barely been able to nail down a role in even the AHL. He’s been demoted to the ECHL twice, and this year was suspended by the team after refusing to report. He’s since been recalled. It’s a safe bet that Gropp won’t be in the Rangers’ organization by the time summer rolls around, if not earlier. His selection at 41st overall was bizarre at the time and looks no better in hindsight. The Rangers traded speedy 26-year-old winger and just a few years later have absolutely nothing to show for it.

3. Ryan McDonagh, J.T. Miller to Tampa Bay for Vlad Namiestnikov, Libor Hajek, Brett Howden, First-Round Pick, Second-Round Pick

Date: February 26th, 2018

In a period where the Rangers were making big moves, this was, by far, the biggest of all. Ryan McDonagh’s departure was inevitable. The team recently announced that they were rebuilding. Paying a premium price for a soon-to-be 29-year-old defenseman does not fit such a plan. Trading the young J.T. Miller was more surprising but did come with some logic. Miller needed a new contract and was arbitration eligible. There were also some off-ice concerns.

In return, the Rangers received a massive trade package. At least, in terms of quantity and optics.

Namestnikov did not play his best hockey in New York and was sent to Ottawa just a few months ago for a fifth-round pick and AHL defenseman Nick Ebert.

Brett Howden was a quality prospect but has mostly struggled in the NHL. Based on the Goals Above Replacement metric available at Evolving Hockey, Howden has been the eighth-worst forward in the NHL over the past two seasons.

Libor Hajek had a horrendous rookie AHL season, showed decently in a quick 2018-2019 cameo, and has been very bad in the NHL this season. CSA Hockey has him as the third-worst defenseman in the NHL this year by expected plus/minus.

Fortunately, the Rangers have made up some ground with their draft selections. Defenseman Nils Lundkvist was taken with the first-round pick and is currently lighting up the Swedish Hockey League. Center Karl Henriksson, drafted with the second-round pick, is a project of sorts but possesses a fairly high ceiling.

There are four players in this trade who are under the age of 21, so it’s too early to make an official judgment on this trade. We can say that the early returns have been pretty poor. The Rangers gave up a bonafide #1 defenseman and a young forward who is now producing at a point-per-game clip in Vancouver. Two-and-a-half years later, the Rangers appear to have a forward who will maybe be a bottom-six player if he can get it together, a defenseman who is trending towards write-off territory (though I’d bet the team disagrees), a couple of prospects, and a fifth-round pick.

We can only work with the information available to us now. We won’t really know the full extent of how good or bad it is until a few more years. So, this ranking receives an asterisk of sots. The Rangers better hope that Howden finds his game and/or that Lundkvist and Henriksson are the real deal. If so, this trade could move way down the list or off of it altogether. If not, it could become one of the worst in team history.

2. Aleksi Saarela, Two Second-Round Picks to Carolina for Eric Staal

Date: February 28th, 2016

This is like the Bryan McCabe trade but on steroids. The 2015-2016 New York Rangers were exceptionally unexceptional. They started the season 15-3-2 but were playing terribly and rode incredible goaltending from Henrik Lundqvist and Ondrej Pavelec. At the time of the trade, the Rangers had 20 wins in their last 40 games and just barely ahead of the Islanders to maintain the third spot in the Metropolitan Division. The Rangers were certainly a playoff team, but no realistic observer pegged them to be a contender of any sort.

Regardless, the Rangers pressed on. They moved a B-level prospect in Aleksi Saarela and two second-round picks to Carolina in return for Eric Staal, who was having an off-year with the Hurricanes.

One issue with the trade was the timing of it. This team wasn’t a serious contender, and they had already given away a ton of draft picks in previous trades. The Rangers weren’t exactly dealing from surplus here.

The trade was also bizarre because it didn’t really address any needs for the Rangers. They already had Derick Brassard, Derek Stepan, Kevin Hayes, J.T. Miller, and Oscar Lindberg as capable center options. It seemed like the Rangers made a trade just for the sake of it.

Staal scored three goals and added three assists in 20 games. He went pointless in five playoff games as the Rangers suffered an embarrassing first-round loss against Pittsburgh.

Saarela has been an elite AHL center and, now 22 years old, recently played his first NHL games. His future is a toss-up. Even if there’s no NHL future for him, the principle of trading him was poorly thought out. The same holds true for the two second-round picks. Even if the prospect pool has recovered (and then some) since, it’s hard to argue that they wouldn’t be better off with three prospects of a decent caliber in the system.

This trade is the most well-rounded on this list. It was poorly conceived and made little sense at the time and it looks just as bad, if not worse, in hindsight. An inarguable, unmitigated disaster.

1A. Anthony Duclair, John Moore, First-Round Pick, Second-Round Pick to Arizona for Keith Yandle, Chris Summer, Fourth-Round Pick

1B. Keith Yandle to Florida for Fourth-Round Pick, Sixth-Round Pick

I’m cheating a little bit here by combining two trades, but they play into each other and are necessary for the complete story of why the Keith Yandle acquisition was a mess.

Yandle’s acquisition was actually well thought out. The Rangers were challenging for the Presidents’ Trophy (and ultimately won it). They were gunning for the Stanley Cup, and the team was desperate to add an offensive defenseman. At the time, Yandle was just about as good offensively as anyone not named Erik Karlsson. He also had another year on his contract, meaning that he wasn’t just a rental. And the Coyotes ate half of his cap hit? Even better. Trading Duclair was controversial but defendable.

Most people would have agreed at the time that Yandle was one of the top defensemen in the NHL. The price the Rangers paid to acquire him certainly reflected that. Did this prevent Head Coach Alain Vigneault from deploying Yandle like a third-pairing power play specialist half of the time? Reader, it did not. During the 2014-2015 season, Yandle ranked sixth among Rangers defensemen by five-on-five time-on-ice. During the 2015-2016 season, he ranked fifth.

This trade is a great example of a lack of communication between front office and coaching staff. First of all, that was terrible coaching by Vigneault. But if that’s how he felt about Yandle then it is what it is. Why, then, would the Rangers pay such a price to acquire him if that’s how the coaching staff was going to use him?

Even despite his absurd usage, Yandle played very well for the Rangers. The 2015-2016 season was going nowhere and the Rangers had a choice to make with impending free agent Keith Yandle. Either re-sign him or trade him as a rental to another team, recouping some of the assets lost in the initial trade.

They picked neither. They kept Yandle past the deadline (and doubled down by adding Eric Staal) in a doomed season, went absolutely nowhere, and then in June traded his rights to Florida for a couple of late draft picks.

The Rangers did us two of the three acquired draft picks on Tarmo Reunanen and Tyler Wall, who are decent prospects still within the organization. Perhaps they will help to save face down the line. Acquiring Yandle was a good move. It’s everything that transpired afterward which make this sequence of trades the worst of the decade.