The NHL trade deadline is a worrying time for NHL fans. You’ve likely spent the past few days regularly refreshing Twitter to see if your team has mortgaged the future to win now only to disappoint you in the spring. Relax. The worst deals tend to happen around the draft, but that’s a story for another day.
With that, let’s take a look at the worst deadline deals by each NHL team since the 2004-05 lockout. And if you’re wondering why your team’s worst trade ever isn’t included, it’s because we’re only including deals that occurred within a week and a half of the trade deadline during the post-lockout era.
Anaheim Ducks – 2008
To Anaheim: Ryan Whitney
To Pittsburgh: Chris Kunitz and Eric Tangradi
Kunitz had a couple solid seasons in Anaheim, but the Ducks needed defensive help and Kunitz was starting to fall out of favor. At the time, Whitney addressed a need for a contending Anaheim team. Whitney was moved to the Edmonton Oilers the following season, but Kunitz became Sidney Crosby’s wingman and won three Stanley Cups in the process.
Arizona Coyotes – 2006
To Arizona: Oleg Kvasha, a conditional fifth-round pick in 2006 (Brett Bennett)
To NY Islanders: Third-round pick in 2006 (Brad Marchand)
The Coyotes have a solid track record on deadline day. No notable busts, but no big moves, either. But one that’s often forgotten is the trade that sent a third-round pick to the Islanders at the 2006 deadline for Oleg Kvasha and a draft pick later used to select Brett Bennett. Kvasha had 11 points in 15 games before bolting off to Russia to finish his career while Bennett never went pro. The third-round pick looked like nothing at the time and the Islanders ended up moving the pick in a later swap. Who could have predicted the selection would produce 100-point pest Marchand?
Boston Bruins – 2015
To Boston: Brett Connolly
To Tampa Bay: A second-round pick in 2015 (Matthew Spencer) and 2016 (Boris Katchouk)
Had the Joe Thornton trade happened later in the season, it would have qualified. Fortunately, most of the team’s other trade disasters happened around the draft, so the loss of this specific Connolly deal doesn’t hurt too much. Katchouk and Spencer still haven’t emerged as NHLers, but given the fact Connolly had 27 points in 73 games during his time in Boston, the value just wasn’t there. He has since become a 20-goal scorer elsewhere, but the Bruins didn’t get much from a player brought in for that specific reason. Hindsight is 20-20, but Roope Hintz, Rasmus Andersson and Vince Dunn were still on the board in 2015 and Samuel Girard, Filip Hronek and Carter Hart were available in 2016.
Buffalo Sabres – 2014
To Buffalo: Michal Neuvirth and Rostislav Klesla
To Washington: Jaroslav Halak and a third-round pick in 2015 (traded)
Just days after moving Ryan Miller to acquire Halak, the Sabres sent Halak to Washington in hopes of adding extra depth. Halak struggled in Washington and departed for the Islanders during the off-season, so not much was lost, right? Halak had his best NHL season to date with a 38-17-4 record the following campaign and has emerged as one of the most reliable backup goalies in the league, now with Boston. Neuvirth posted a 6-19-3 record during his tenure in Buffalo before getting moved to the Islanders the next season before an injury-filled tenure in Philadelphia. The Sabres, meanwhile, have struggled to find consistent goaltending. Klesla’s NHL career was over at that point.
Calgary Flames – 2009
To Calgary: Olli Jokinen and a third-round pick in 2009 (Josh Birkholz)
To Arizona: Matthew Lombardi, Brandon Prust and a first-round pick in 2010 (Brandon Gormley)
Jokinen was one of the top trade targets in 2009 and wrangling a star player away for two mid-roster players and a draft pick seemed worth it. At first, it even worked out: Jokinen scored 15 points in 19 games down the stretch and hopes were high that he would help make the Flames a consistent contender. Unfortunately, he was moved to the Rangers in 2010 after struggling for 56 games, though he returned to Calgary months later as a free agent. Even though Lombardi and Prust weren’t game-changers by any means, the first-round pick still could have been valuable. After all, Vladimir Tarasenko was still on the board when Gormley was selected. Too bad.
Carolina Hurricanes – 2016
To Carolina: Aleksi Saarela, a second-round pick in 2016 (traded to Chicago) and 2017 (Luke Martin)
To NY Rangers: Eric Staal
This turned out to be a bad deal for both teams. Staal was Carolina’s third major star, following in the footsteps of Ron Francis and Rod Brind’amour, but Staal was starting to decline with a struggling Hurricanes franchise. Francis, Carolina’s GM at the time, helped add to the team’s prospect base by moving Staal, a pending UFA, for Saarela and two picks. Saarela played just one playoff game with the Hurricanes before going elsewhere, remaining in the AHL at 23 – and yet, he was still the best piece of the deal for the Hurricanes. The redeeming factor? The 2016 pick was used to acquire Teuvo Teravainen, one of Carolina’s most important players, but that was a totally separate deal. Even though Staal was a bust in the Big Apple, the Hurricanes should have been able to get more for an NHL all-star.
Chicago Blackhawks – 2016
To Chicago: Dale Weise and Tomas Fleischmann
To Montreal: Phillip Danault and a second-round pick in 2018 (Alexander Romanov)
The Blackhawks wanted veteran help for another Cup run but an early first-round exit meant the gamble didn’t pay off. Fleischmann had just five points in 19 regular season games and Fleischman sat out three of the seven games in the post-season before retiring due to blood clots. Weise did even less, recording one assist in the regular season and one goal in the post-season before bolting to Philadelphia. Meanwhile, Danault has been a top-six fixture in Montreal over the past four seasons. Not too shabby for a former first-round pick who was moved after scoring just one goal and five points in 32 games with the Blackhawks. Oh, and Romanov has true top-four potential in Montreal, so that’s a bonus.
Colorado Avalanche – 2006
To Colorado: Jose Theodore
To Montreal: David Aebischer
Theodore needed a change of scenery after Cristobal Huet took over in Montreal and Carey Price wasn’t far behind in the pipeline. Theodore was injured when the trade occurred – he had slipped on some ice outside his home – and struggled to perform in Colorado once healthy. At the time, his $6-million cap hit was expensive considering the less-than $50-million limit and he wasn’t brought back after his contract ended. Aebischer was nothing special, but Theodore should have been a more valuable trade asset.
Columbus Blue Jackets – 2019
To Columbus: Ryan Dzingel
To Ottawa: Anthony Duclair, second-round picks in 2020 and 2021
The picks hurt knowing Columbus still needed long-term scoring depth, but Dzingel, paired with Matt Duchene, Artemi Panarin, Pierre-Luc Dubois and Co., was supposed to make the Blue Jackets a legitimate threat for the Cup. The Blue Jackets won a shocking playoff series against Tampa Bay but fell in the second round to Boston, therefore ending the team’s miracle run and the tenure of Duchene, Panarin and Dzingel in Ohio. Duclair, meanwhile, has 22 goals and an all-star game appearance to his credit for a weak Senators team, and those two picks could still turn out to be something worthwhile.
Dallas Stars – 2011
To Dallas: Alex Goligoski
To Pittsburgh: James Neal and Matt Niskanen
Neal may not be the player that he once was, but he was quite important to the Penguins for a handful of seasons. Neal’s best years were spent in Pittsburgh, where he recorded a career-high 40 goals and 81 points in 2011-12 before moving to Nashville in a fantastic deal for the Predators. Niskanen’s best offensive output saw him put up 46 points in a top-four role in 2013-14. Goligoski wasn’t bad by any means and spent six years with the Stars, but the deal didn’t work out in Dallas’ favor.
Detroit Red Wings – 2012
To Detroit: Kyle Quincey
To Tampa Bay: First-round pick in 2012 (Andrei Vasilevskiy)
The Red Wings have a history of moving first-round picks to acquire help. For reference, the Red Wings had just four first-round picks from 2001 until 2012, with Jakub Kindl proving to be the best selection. But this deal in particular turned out awful. Quincey did little to spark a fire in Detroit and the Red Wings failed to make it out of the first round that season. The pick the Wings moved turned into Vasilevskiy, the 2019 Vezina Trophy winner. Detroit could really use his goaltending services right now.
Edmonton Oilers – 2007
To Edmonton: Robert Nilsson, Ryan O’Marra and a first-round pick in 2007 (Alex Plante)
To NY Islanders: Ryan Smyth
Sorry Oilers fans, you knew this was coming. Smyth. Captain Canada. The emotional post-trade press conference. Smyth was such an integral part of the Oilers franchise and a proven 30-goal, 50-point scorer. In fact, the year he was traded, Smyth had 53 points in as many games and was hoping to sign a new contract. That didn’t materialize and he was moved for three guys that totalled 107 points in an Oilers uniform. Smyth didn’t sign in Long Island and instead bolted to Denver and then moved on to Los Angeles before finishing with a three-year stint in Edmonton.
Florida Panthers – 2010
To Florida: Byron Bitz, Craig Weller, second-round pick in 2010 (Alex Petrovic)
To Boston: Dennis Seidenberg and Matt Bartkowski
Bitz and Weller played a combined seven games for Florida. Petrovic was a depth option for Florida for seven years before his contract became a cap headache and eventual salary dump. Going the other way? Seidenberg, who had a good run on Boston’s second pairing and helped the Bruins win the ultimate prize in 2011. That alone was worth the price, as Bartkowski never was a full-time contributor with the Bruins and has spent most of the past two years with the AHL’s Iowa Wild.
Los Angeles Kings – 2011
To Los Angeles: Dustin Penner
To Edmonton: Colton Teubert and a first-round pick in 2011 (Oscar Klefbom)
In 2011, the Kings were looking to add a scoring winger. Penner was supposed to be that guy. Despite a 32-goal season with the Oilers in 2009-10, though, Penner had just 11 goals over parts of three campaigns with the Kings. While he had a good playoff run en route to a Stanley Cup in 2012, Penner’s didn’t provide a real return on investment. Teubert didn’t manage to develop into the blueliner the Oilers had hoped, but Klefbom is one of Edmonton’s best players. Shoutout to the deal with Arizona that brought Scott Wedgewood and Tobias Rieder to Los Angeles for Darcy Kuemper. The Kings could have really used Kuemper right now.
Minnesota Wild – 2017
T0 Minnesota: Martin Hanzal, Ryan White and a fourth-round pick in 2017 (Mason Shaw)
To Arizona: Grayson Downing, first-round pick in 2017 (Pierre-Olivier Joseph) and a second-round pick in 2018 (Kevin Bahl)
The cost of rentals increases the potential for disaster, and that’s what this deal was: a disaster. Sitting first in the Western Conference at the time, Hanzal was supposed to bring scoring punch and center depth to Minnesota. But the gamble didn’t pay off. The Wild were ousted from the post-season in five games and Hanzal scored one goal. In the off-season, he bolted to Dallas, where injuries have limited him to just 45 games over three seasons. Rubbing some additional salt in the wound is that the two picks the Wild traded away have become solid prospects.
Montreal Canadiens – 2008
To Montreal: A second-round pick (traded to Atlanta)
To Washington: Cristobal Huet
Most of Montreal’s deadline deals over the past 15 years have been to address depth issues, but moving Cristobal Huet for a second-round pick didn’t pay off. Halak only played 13 games with Washington but had an 11-2-0 record and helped lead the team to a (short) playoff run before winning the Stanley Cup two years later in Chicago. Montreal moved the pick (which became Jeremy Morin) to grab Mathieu Schneider (and Joonas Nattinen, who played one NHL game) from Atlanta the following year for 23 games. He played well, for sure, but, again, hindsight would suggest grabbing someone like Robin Lehner a pick later or Dmitri Orlov a few picks later would have been much more beneficial.
Nashville Predators – 2015
To Nashville: Cody Franson and Mike Santorelli
To Toronto: Olli Jokinen, Brendan Leipsic and a first-round pick in 2015 (Travis Konecny)
Toronto didn’t really benefit from this deal, but Nashville probably wishes they could take back the draft pick. Franson and Santorelli were supposed to bring an added punch to Nashville’s playoff run but were instead scratched at points during the post-season. The first-round pick turned out to be Konecny (the Leafs moved the pick to Philadelphia), but Sebastian Aho – the No. 1 center the Preds could really use today – was also available when Konecny was selected.
New Jersey Devils – 2018
To New Jersey: Michael Grabner
To NY Rangers: Yegor Rykov and a second-round pick in 2018 (traded to Ottawa)
Good news, Devils fans! Your favorite team hasn’t had many deadline deal disasters. The Grabner deal was a bust, though, and it didn’t take an expert to see that coming. Even though the cost wasn’t drastic, the Devils likely would have preferred to have Johnny Tychonik, Kevin Bahl, Calen Addison or Akil Thomas in the system over a player who produced a whopping five points in 21 games. Grabner’s on pace for 15 points this season in Arizona, so there’s that.
New York Islanders – 2014
To NY Islanders: Sebastian Collberg, a conditional second-round pick (traded to NY Rangers)
To Montreal: Thomas Vanek, a conditional fifth-round pick in 2014 (Nikolas Koberstein)
The Islanders haven’t typically made major deadline duds because, frankly, they haven’t had the need to attempt a big splash. That’s the silver lining of spending several years on the outside of the post-season picture and out of true contention. In fact, they’ve made quite a few smart deals over the past few years. And even this Vanek deal wasn’t that bad because it prevented the Islanders from committing to a terrible contract. The return still wasn’t enough, though. Collberg didn’t play a game with the Islanders and he’s 11th in scoring with his Austrian team this season. This trade tree led the Islanders to nab Josh Ho-Sang in the draft, but that hasn’t worked out, either.
New York Rangers – 2018
To NY Rangers: Vladislav Namestnikov, Libor Hajek, Brett Howden, a first-round pick in 2018 (Nils Lundkvist) and a conditional second-round pick in 2019 (Karl Henriksson)
To Tampa Bay: Ryan McDonagh, J.T. Miller
Uh, yeah. This deal happened. McDonagh has been a great piece for the Lightning and Miller was a good secondary option before the team moved him to Vancouver. Namestnikov, on the other hand, was moved to Ottawa for an AHL defensemen and Hajek and Howden are just depth guys. The two prospects are promising, but they’re still just prospects. Nothing is certain at this point.
Ottawa Senators – 2013
To Ottawa: Cory Conacher and a fourth-round pick in 2013 (Tobias Lindberg)
To Tampa Bay: Ben Bishop
Craig Anderson has been great for the Senators. Often over the past decade, he has been one of Ottawa’s best players. But those days are coming to an end and there’s no high-end replacement in sight. So just imagine if the Senators managed to keep Bishop – a multi-time Vezina Trophy finalist – and deal Robin Lehner instead. Conacher didn’t build on what was a stunningly successful start rookie season and eventually returned to Tampa Bay in 2016-17, where he has remained since. Bishop may not have lasted in Ottawa, but in hindsight? Ouch.
Philadelphia Flyers – 2014
To Philadelphia Flyers: Andrew MacDonald
To NY Islanders: Matt Mangene, a third-round pick in 2014 (Ilya Sorokin) and a second-round pick in 2015 (traded to Boston)
Ask any Flyers fan about the worst contract in Flyers history and MacDonald’s name will be in the conversation alongside Ilya Bryzgalov. MacDonald was a disaster in Philadelphia, struggling to handle top-four duty and eventually landing in the AHL. Instead, the Flyers could have had Sorokin, one of the game’s top goaltending prospects, and perhaps the Flyers would have had one of the best 1-2 punches in the NHL.
Pittsburgh Penguins – 2018
To Pittsburgh: Derick Brassard, Vince Dunn, Tobias Lindberg and a third-round pick in 2018 ()
To Ottawa: Ian Cole, Filip Gustavsson, a first-round pick in 2018 () and a third-round pick in 2019 ()
To Vegas: Ryan Reaves and a fourth-round pick in 2018
On to the most complicated trade. Let’s just say this: not a single asset acquired by Pittsburgh is still with the club and with 23 points in 54 games, Brassard didn’t add what the Penguins believed he could. The first-round pick given away by Pittsburgh was moved to the Rangers and eventually became K’Andre Miller. He’s considered one of top blueline prospects in the game. That hurts.
San Jose Sharks – 2007
To San Jose: Craig Rivet and a fifth-round pick in 2007 (Julien Demers)
To Montreal: Josh Gorges and a first-round pick in 2008 (Max Pacioretty)
At the time, this looked like a solid piece for the Sharks. The team wanted to add a veteran presence to the backend and Rivet was a nice addition over a younger, inexperienced Gorges at the time. The first-round pick was worth the price, right? Well, Rivet played another full season with the Sharks and had a career-high 35 points as a big-bodied defender on a contender, but Gorges became one of Montreal’s top-four defenders for the next decade and Pacioretty bloomed into one of the league’s most consistent wingers. Demers never turned pro, so, no, the pick wasn’t worth it.
St. Louis Blues – 2014
To St. Louis: Ryan Miller and Steve Ott
To Buffalo: Jaroslav Halak, Chris Stewart, William Carrier, a first-round pick in 2016 (Jack Roslovic) and a third-round pick in 2016 (Linus Nassen)
Again, this is a deal that made sense at the time. Miller had some good hockey left in him and was supposed to be an upgrade over Halak in all respects. But Miller was only OK in the regular season and imploded in the playoffs. He posted an .897 save percentage in a six-game first-round defeat at the hands of the rival Blackhawks. Neither goalie in the deal stuck around long (Halak never got to play for Buffalo and was traded to Washington shortly after while Miller moved to Vancouver during the off-season), but Halak has gone on to be one of the NHL’s best backup goaltenders and a valuable asset heading into free agency this summer.
Tampa Bay Lightning – 2008
To Tampa Bay: Jeff Halpern, Jussi Jokinen, Mike Smith and a fourth-round pick in 2009 (traded)
To Dallas: Brad Richards and Johan Holmqvist
Without the incredible play of Richards, the Lightning likely wouldn’t have won the 2004 Stanley Cup. However, the salary cap era meant keeping the team’s dynamic trio of Richards, Vincent Lecavalier and Martin St-Louis together was going to be impossible, but the return for one of the team’s top stars was minuscule. Smith had some decent seasons in Tampa Bay, but the team failed to acquire the true No. 1 goaltender they needed and Halpern and Jokinen’s stints were rather forgettable.
Toronto Maple Leafs – 2010
To Toronto: Luca Caputi and Martin Skoula
To Pittsburgh: Alexei Ponikarovsky
The Leafs were busy leading up to the 2010 trade deadline, making seven deals between Jan. 31 and March 3 – albeit, most deals were small after the acquisition of Dion Phaneuf in January. On March 2, the Leafs moved pending UFA Ponikarovsky in order to restock the prospect base and Caputi seemed quite a catch at the time. As it turned out, Caputi failed to deliver on the promise he possessed, lasting just 26 games in Toronto. He never played another NHL game after the 2010-11 season.
Vancouver Canucks – 2015
To Vancouver: Sven Baertschi
To Calgary: A second-round pick in 2015 (Rasmus Andersson)
The Canucks’ trade history is checkered, but somehow they’ve managed to avoid blunders at the deadline. Had Jacob Markstrom not emerged as a solid option in the Canucks crease, maybe the Roberto Luongo deal lands here. Instead, it’s the Baertschi deal. He was projected to be a top-six forward, but after a decent start to his time in Vancouver, he has since landed in the AHL. Andersson, meanwhile, has enjoyed time on Calgary’s top defensive pairing and is part of the team’s core moving forward.
Vegas Golden Knights – 2018
To Vegas: Tomas Tatar
To Detroit: A first-round pick in 2018 (Joe Veleno), a second-round pick in 2019 (Robert Mastrosimone) and a third-round pick in 2021
The Golden Knights don’t have a lengthy trade history. That comes with the expansion territory. But if we were to do this exercise again in several years’ time, chances are it’d look much the same as acquiring Tatar for three draft picks turned out to be quite the gaffe. He had just six points in 20 regular season games and another two points in eight playoff games between bouts as a healthy scratch. Tatar was eventually sent to Montreal to bring over Max Pacioretty. That wasn’t a terrible deal, but losing Nick Suzuki – a forward with No. 1 center potential – was also painful. It’s still too early to judge the prospects, but Joe Veleno is a nice piece for the Red Wings.
Washington Capitals – 2013
To Washington: Martin Erat and Michael Latta
To Nashville: Filip Forsberg
This one doesn’t require much explanation. Forsberg has become a franchise cornerstone in Nashville while Erat scored just two goals in 62 total games with the Capitals before he was moved to Arizona. Latta had 17 points in 113 games with the Capitals before embarking on a career in Europe. This is deal looked awful at the time and somehow continues to look worse with each passing day.
Winnipeg Jets – 2012
To Winnipeg: second-round pick in 2012 (traded to Washington) and a third-round pick in 2012 (J.C. Lipon)
To Chicago: Johnny Oduya
Oops. Oduya was a significant part of two Stanley Cup victories with the Blackhawks and left a hole on Winnipeg’s blueline. After a bit of wheeling and dealing, this deal turned into four prospects for the Jets, but only Tucker Poolman done anything meaningful in Winnipeg. Even then, he wasn’t an everyday NHLer until this season.
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