The most lopsided deadline trades in NHL history
The NHL trade deadline is a delicate dance between the needs of today vs. the wants of tomorrow.
Every season, there are teams that sacrifice the future through picks or prospects in an attempt to contend for a championship. Every season, there are teams that ship out players because of financial considerations, hoping to make the most of that monetary bind with some future assets. And then, in a few seasons, these moves are brought into focus through the glorious benefit of hindsight.
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Here are the 20 most lopsided deals in the history of the NHL trade deadline. Please note that we did weigh the impact of players who were selected via draft picks involved in these trades, in the sense that the offending teams would have had a shot at them, or other talented players around them. We’ve also included a “trade tree” for each that examines how these teams utilized their acquired assets through the ensuing years. Please also note that this list is limited to moves made around the deadline, so trades made in the summer or preseason are not included. Enjoy!
Note: Read through the entire list, or jump ahead to a particular trade by clicking here:
Tatar (2018) | Goligoski (2011) | Hossa (2008)
Francis (1991) | Hull (1988) | Take me to No. 1!
The deal: The New York Islanders traded G Chris Osgood and their third-round choice in the 2003 draft (eventually used on Konstantin Barulin) to the St. Louis Blues for C Justin Papineau and St. Louis’ second-round choice in the 2003 draft (Jeremy Colliton) on March 11, 2003.
In hindsight: Osgood won 49 of 103 games with the Islanders. But when it came to a new contract, his ask was too high. “Truth be told, we were going to part company with Chris at the end of the year because of the contract situation,” Islanders general manager Mike Milbury said at the time. “We did get what we believed to be something of value for Chris. There was not a large market for goalies at this stage of the system.”
Papineau played with the Islanders through 2004, which was the end of his NHL career. Colliton would be a spare part for five seasons. Osgood? He won 31 games for the Blues in 2003-04 before returning to the Red Wings to win a third Stanley Cup.
Trade tree: One didn’t exactly sprout here, although it is noteworthy that the man who would eventually replace Joel Quenneville as head coach of the Chicago Blackhawks was a part of this deal.
The deal: The Chicago Blackhawks traded Cam Barker to the Minnesota Wild for Kim Johnsson and Nick Leddy on Feb. 12, 2010.
In hindsight: There was some method to this madness. Johnsson apparently wasn’t going to re-sign with the Wild, and he played only eight games with the Blackhawks because of concussion symptoms. Leddy played four seasons with Chicago — including all 23 games of the Blackhawks’ 2013 Stanley Cup-winning playoff run — before becoming the same kind of salary-cap casualty that Barker was. As for Barker … yeesh. He played 71 games with the Wild, tallying 12 points with a minus-12 rating. The Wild bought him out in June 2011, he signed with the Edmonton Oilers, lasted a year there and then went full sail into journeyman status and career retrospectives like this one.
Trade tree: Leddy was traded to the Islanders on Oct. 4, 2014, for three players who never saw action for the Blackhawks (Ville Pokka, T.J. Brennan and Anders Nilsson), and all of a sudden he was a top-pairing guy.
The deal: The San Jose Sharks traded F Ville Nieminen, F Jay Barriball and New Jersey’s first-round choice in the 2007 draft (David Perron) to the Blues for F Bill Guerin on Feb. 27, 2007.
In hindsight: Guerin was a big deadline addition for the Sharks, having resurrected his career in St. Louis with a 28-goal season. He had eight goals in 16 games for the Sharks but was a postseason bust, with just two assists in nine games. Yes, seeing that this “cost” them Perron stings, but that’s just some good drafting from the Blues. And Guerin isn’t exactly the first Shark to disappoint in the playoffs.
Trade tree: Is there a tree that grows in a circle? Because Perron is now in his third tour of duty with the Blues.
The deal: The San Jose Sharks traded D Josh Gorges and their first-round pick in 2007 (Max Pacioretty) to the Canadiens for D Craig Rivet and Montreal’s fifth-round choice (Julien Demers) on Feb. 25, 2007.
In hindsight: Rivet wasn’t a disaster, playing 91 regular-season and 24 playoff games in two seasons. But he wasn’t Gorges, whom the Sharks traded away at 22 years old and watched play 687 career games with Montreal and Buffalo. And he certainly wasn’t Pacioretty (nor Perron nor Mikael Backlund, all of whom were available at that point in the draft).
Trade tree: Rivet was moved to Buffalo in July 2008 in an inconsequential move. Gorges eventually signed with the Buffalo Sabres too, while Pacioretty was moved to Vegas for Nick Suzuki, Tomas Tatar and a second-rounder after 626 games, 448 points and a reign of captaincy in Montreal.
The deal: The Tampa Bay Lightning traded C Brad Richards and G Johan Holmqvist to the Dallas Stars for G Mike Smith, F Jussi Jokinen, F Jeff Halpern and Dallas’ fourth-round pick (later traded to Minnesota, later traded to Edmonton; Edmonton selected Kyle Bigos) on Feb. 26, 2008.
In hindsight: The Lightning got buyer’s remorse with Richards, trading him two years after inking him to a massive contract that carried a $7.8 million cap hit. He’d play four seasons in Dallas before leaving for the New York Rangers on a massive free-agent deal. Smith and Jokinen didn’t find their games until they left Tampa. Halpern would play 126 games for the Bolts with 51 points and a minus-24. The Stars got a 90-point center; the Lightning got spare parts.
Trade tree: Jokinen was eventually traded for defensemen Wade Brookbank and Josef Melichar and future considerations. Halpern was traded to Los Angeles in 2010 for Teddy Purcell, who had a memorable run of 17 points in 18 games in the 2011 playoffs for Tampa. Purcell was infamously traded in 2014 for Sam Gagner, who was immediately shipped to the Coyotes.
The deal: The Vegas Golden Knights traded their 2018 first-round pick (Joe Veleno), the Islanders’ 2019 second-round pick and a 2021 third-round pick to the Red Wings for F Tomas Tatar on Feb. 26, 2018.
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In hindsight: Our most recent entry in the top 20, the Knights went all-in with Tatar. Alas, he managed just four goals in 20 games in the regular season, and then one goal in eight games in the postseason, where the big deadline coup was [checks notes] a healthy scratch for much of their epic playoff run.
Trade tree: Tatar was successfully repackaged that summer in a trade, going to the Montreal Canadiens with 2017 first-rounder Suzuki and Columbus’ second-round pick in the 2019 draft for Pacioretty.
The deal: The Los Angeles Kings traded their first-round pick in the 1982 draft (Phil Housley) to the Buffalo Sabres for D Jerry Korab on March 10, 1980.
In hindsight: Jerry Korab was a fine defensive defenseman who actually made a pair of All-Star Games in the 1970s. He played 211 games for the Kings after the trade. It’s just that, you know, he’s not Phil Housley, whom the Sabres drafted with that pick and who made the Hall of Fame with 1,232 points in 1,495 career games.
Trade tree: Housley was later included in an absolute blockbuster in 1990, packaged with two players (Scott Arniel and Jeff Parker) and a first-round pick that became Keith Tkachuk in exchange for Dale Hawerchuk and a first-rounder that became Brad May.
The deal: The Toronto Maple Leafs traded F Darby Hendrickson, LW Sean Haggerty, D Kenny Jonsson and their first-round draft pick in 1997 (Roberto Luongo) to the New York Islanders for F Wendel Clark, D Mathieu Schneider and D D.J. Smith on March 13, 1996.
In hindsight: This is so very, very Leafs: the cult-like obsession with Clark, who was brought home after 95 games with Quebec and the Islanders. They mortgaged the future for a fruitless present, as they went all-in only to get sent home by the Wayne Gretzky Blues in the Western Conference quarterfinals. And of course, their choice of mortgage: Jonsson played 597 games with the Islanders. Similar to the aftermath of the ill-fated Tom Kurvers trade that gifted the third overall pick in the 1991 draft to the Devils (and with it, Hall of Famer Scott Niedermayer), the Leafs dropped 12 points in the standings and the Islanders ended up with the No. 4 pick in 1997 and selected Luongo, who sits fourth on the NHL all-time goalie wins list with 483.
Trade tree: Clark and Schneider were gone via free agency in 1998. Luongo would later be involved in a significantly worse trade — going to Florida with Olli Jokinen for Mark Parrish and Oleg Kvasha — but alas, Milbury’s debacle took place in June.
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The deal: The Dallas Stars traded F James Neal and D Matt Niskanen to the Pittsburgh Penguins for D Alex Goligoski on Feb. 21, 2011.
In hindsight: Goligoski had three things going for him: his youth (25 at the time), being an offensive defenseman and having won a Stanley Cup with the Penguins. But Pittsburgh had Kris Letang, Paul Martin and Zbynek Michalek, and that made him expendable. The Stars sold low on Niskanen, and the Penguins coveted the 23-year-old Neal as a power forward. Turns out, their obsession was warranted: Neal scored 184 points in 199 games with the Penguins, including a 40-goal season. Goligoski (0.49 points per game in 385 games) was only a shade ahead of Niskanen (0.40) as far as production, but did find a nice niche in the latter part of his six-season run as a defense partner for John Klingberg. But Dallas, in hindsight, overpaid.
Trade tree: The Stars traded pending free agent Goligoski in June 2016 to Arizona, where he’d sign a new deal and be generally underwhelming. The Penguins saw Niskanen leave for Washington as a free agent in 2014, while Neal was flipped to Nashville for forward Patric Hornqvist in one of the most critical trades for Pittsburgh’s back-to-back Cup wins.
The deal: Atlanta Thrashers traded D Braydon Coburn to the Philadelphia Flyers for D Alexei Zhitnik on Feb. 24, 2007.
In hindsight: Ugh. In Coburn, the Thrashers had a promising 21-year-old blueliner who had been drafted eighth overall in 2003. In Zhitnik, they were trading for a 34-year-old defenseman whose best years were far behind him, having been traded for a second time that season. Zhitnik failed to register a point in the Thrashers’ four-game playoff loss to the Rangers. Coburn would play 576 games with the Flyers, scoring 161 points with a plus-24.
Trade tree: Zhitnik played 83 games with Atlanta before leaving for the KHL. Coburn was traded in 2015 in a deal that brought defenseman Radko Gudas to Philadelphia.
The deal: The Edmonton Oilers traded F Miroslav Satan to the Buffalo Sabres for F Barrie Moore and D Craig Millar on March 18, 1997.
In hindsight: As the saying goes, “follow the money.” GM Glen Sather didn’t want to spend it on a 22-year-old winger with clear offensive upside, and was worried about Satan leaving for Europe without the Oilers getting compensation if his next contract offer was unsatisfactory. So he traded him for Millar, who would play 36 games for Edmonton, and Moore, who would play four. Satan, meanwhile, would become a star with the Sabres, win a Cup with the Penguins and score 735 career points in 1,050 games. As the saying goes, “the devil’s in the details” when it comes to trading Satan.
Trade tree: Oddly enough, this was the only time Satan was traded in his NHL career. Millar was later sent to Nashville in June 1999 for Detroit’s third-round choice and a bit of solace: That pick landed Edmonton Mike Comrie.
The deal: The Phoenix Coyotes traded C Danny Briere and their third-round pick in the 2004 draft (Andrej Sekera) to the Sabres for C Chris Gratton and Buffalo’s fourth-round choice in 2004 (later traded to the Oilers, who selected Liam Reddox) on March 10, 2003.
In hindsight: This was actually a sell-off move for the Sabres, who had declared bankruptcy earlier in the season and were waiting for new owner B. Thomas Golisano to complete a deal for the team. Gratton was the Sabres’ second-leading scorer, but the Sabres were also his third NHL team in 10 seasons. “[Briere’s] a couple of years younger. He’s certainly a different type of player and I think it’s a good fit for us considering where we’d like to go,” said Buffalo GM Darcy Regier. “He’s got upside.”
That he did. Gratton lasted two seasons in Phoenix, played 1,092 games in the NHL with 568 points; Briere played only 973 games, but had 696 points. Sekera, meanwhile, played seven seasons in Buffalo.
Trade tree: Sekera was traded in 2013 for Jamie McBain and Carolina’s second-round pick (J.T. Compher). Gratton was traded to the Colorado Avalanche in March 2004 with Ossi Vaananen and Phoenix’s second-round choice in the 2005 draft for Derek Morris and Keith Ballard. That second-round pick would end up being Paul Stastny, meaning that Chris Gratton barely missed making the top 20 twice.
The deal: The Atlanta Thrashers traded RW Marian Hossa and F Pascal Dupuis to the Pittsburgh Penguins for C Colby Armstrong, F Erik Christensen, F Angelo Esposito and Pittsburgh’s first-round pick in the 2008 draft (Daulton Leveille) on Feb. 26, 2008.
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In hindsight: The Thrashers faced a ticking clock to unrestricted free agency for Hossa, but also faced a robust market for one of the top scoring wingers in the league. GM Don Waddell settled on this offer from the Penguins, which featured two forwards with limited offensive upside, a draft bust and a low first-rounder. Hossa helped the Penguins get to their first Stanley Cup Final, before taking his talents to Detroit and then to Chicago, where he won three Cups. Dupuis, a practical throw-in (!) on this deal, won a Cup with Pittsburgh in 2009. Esposito never played in the NHL. By 2010, both Armstrong and Christensen were gone.
Trade tree: Christensen was traded to Anaheim in 2009 for C Eric O’Dell, who played 41 games with the Jets after Atlanta relocated, thanks in part to trades like this.
The deal: The Ottawa Senators traded G Ben Bishop to the Tampa Bay Lightning for F Cory Conacher and Philadelphia’s fourth-round pick in the 2013 draft (Tobias Lindberg) on April 3, 2013.
In hindsight: The Senators figured they could move Bishop because he was behind Robin Lehner on the organizational depth chart. They figured Conacher, a pending RFA, wasn’t just a product of the elite talent with whom he was playing. Some felt GM Steve Yzerman had been fleeced. But clearly, he was selling high: Conacher tallied just 25 points in 72 games with Ottawa, who dropped him on waivers the following season. Bishop was a starter for Tampa in 2013-14, and remains one of the NHL’s top netminders.
Trade tree: The Lightning would trade Bishop in February 2017 for Peter Budaj, Erik Cernak, Los Angeles’ seventh-round pick in 2017 draft and a conditional pick in the 2017 draft, clearing the decks for Andrei Vasilevskiy.
The deal: The Hartford Whalers traded C Ron Francis, D Grant Jennings and D Ulf Samuelsson to the Pittsburgh Penguins for C John Cullen, RW Jeff Parker and D Zarley Zalapski on March 4, 1991.
In hindsight: Other than tanking to draft Mario Lemieux, no other move had as great an impact on the Penguins’ Stanley Cup wins in the early 1990s as this trade. “Certainly, we weren’t a championship-caliber team, in my opinion, until we made that deal to get Ronnie and Ulf and Grant Jennings,” then-GM Craig Patrick said in 2006. The Penguins did give to get — Cullen was a 110-point forward and Zalapski was a young offensive defenseman with upside — so the initial analyses suggested the Whalers did well. But what they got, compared with what they sent out … well, there is no comparison.
Trade tree: Samuelsson was flipped in a momentous trade for the Penguins, going to the Rangers with Luc Robitaille for Petr Nedved and Sergei Zubov. Jennings was traded to Toronto for Drake Berehowsky. Hartford traded Cullen to Toronto for a pick that became defenseman Vlastimil Kroupa. Zalapski was also moved in a blockbuster, traded with James Patrick and Michael Nylander to the Flames for Gary Suter, Paul Ranheim and Ted Drury.
The deal: The Los Angeles Kings traded F Butch Goring to the New York Islanders for RW Billy Harris and D Dave Lewis on March 10, 1980.
In hindsight: When teams talk about finding the final piece of a championship puzzle, they’re talking about the Goring trade. The Kings had signed Goring, then 29, to a six-year deal two years earlier. The team seemed to value him as much as the fans adored him. To this day, Goring is baffled by the decision to move him … while being thankful the Kings did. Goring won the Conn Smythe in 1980-81 and had 62 points in 78 playoff games during the Islanders’ run of four straight Cups. He turned the team from a championship contender to a dynasty. He was, as they say, the final piece.
What’s most interesting about this trade, however, is how it’s painted as lopsided because of the Islanders’ team accomplishments and Goring’s postseason acumen. His regular-season numbers weren’t close to what he produced with the Kings, where he was a point-per-game player. As for the return, look at some of the other trades on this list for context. Lewis played 221 games with the Kings. Harris played 128 games. Neither of them is Butch Goring, this is true; hence, it remains a lopsided deadline deal. But maybe not the total disaster that some of these other transactions were.
Trade tree: Harris was moved in 1981 with John Gibson for Leafs defenseman Ian Turnbull, who lasted 42 games. Lewis was traded in 1983 to Minnesota for C Steve Christoff and D Fred Barrett. These deals were … not good.
The deal: The Los Angeles Kings traded their third-round choice in 1981 (Colin Chisholm) and first-round choice in 1983 (Tom Barrasso) to the Buffalo Sabres for F Rick Martin on March 10, 1981.
In hindsight: The Kings didn’t realize they were trading for “R.M.I.N.O.,” or “Rick Martin in name only.” He injured his knee in a 1980 game and later claimed via a lawsuit that the Sabres and coach Scotty Bowman were negligent in not providing proper medical care. (The suit was tossed.) Martin would play just four games for the Kings.
This is another example of the dangers of trading future first-round picks. Barrasso was taken fifth overall in 1983 (ahead of 413-goal scorer John MacLean and Hall of Famer Cam Neely) and won the Calder and the Vezina trophies in 1983-84, the same year the Kings used five goalies and finished last in the West.
Trade tree: The Sabres would later trade Barrasso to the Penguins in 1988 for Doug Bodger and Darrin Shannon, the latter of whom was moved in 1991 to Winnipeg for (among other things) a fifth-rounder that became Yuri Khmylev.
The deal: The Calgary Flames traded RW Brett Hull and LW Steve Bozek to the St. Louis Blues for D Rob Ramage and G Rick Wamsley on March 7, 1988.
Get up to speed ahead of the Feb. 25 deadline, with news, trade target rankings, team needs, grades and more.
With about four months remaining until the draft, we go from 1 to 31 in the first mock of the year.
Will Kirill Kaprizov ever stop scoring? Can Kaapo Kakko make a charge for the No. 1 pick? All that and more in this week’s prospect rundown.
In hindsight: He wasn’t Brett Hull yet, but showed potential, having scored 26 goals in 52 games as a rookie for the Flames. But there was criticism of his skating, attitude and work ethic, so GM Cliff Fletcher decided to move Hull to add the last pieces to a Stanley Cup puzzle, risks being what they were. “We were cognizant of the risk. Hull is going to score a lot of goals in the NHL,” Fletcher said at the time, via the Globe & Mail. “But we evaluated the trade from the standpoint that we have the No. 1 scoring team in the league. And we had not been using Brett in a lot of key games at this stage. Because the chemistry of a lineup — the balance between defense and offence — is critical at this stage of the year, we thought it worth giving up our future in return for a real solid NHL defenseman and goaltender who can do the job in the NHL.”
Going with that logic, the trade worked: Ramage was a key part of the Flames’ lone Stanley Cup in franchise history in 1989. So it’s not that Calgary didn’t get anything out of the deal. It’s just that the Flames gave up what turned out to be the fourth-leading goal scorer in NHL history (741), the 1990-91 Hart Trophy winner and a Hockey Hall of Famer.
Trade tree: Ramage was traded to the Maple Leafs in 1989 for Toronto’s second-round pick, which the Flames used on Kent Manderville. Both Manderville and Wamsley were part of the package in the deal that sent Doug Gilmour to the Leafs in 1992 in an epically bad deal for the Flames.
The deal: The Washington Capitals traded F Filip Forsberg to the Nashville Predators for F Martin Erat and F Michael Latta on April 3, 2013.
In hindsight: After years of holding on to his blue-chip prospects, Capitals GM George McPhee finally dealt one … and ended up on the losing side of one of the most lopsided deals in NHL history. Erat had requested a trade earlier in the season; he requested another one after playing just 62 games in Washington, scoring two goals during a span that saw him as a healthy scratch for the first time in his career. He played in four playoff games, and failed to score a goal. Forsberg, of course, has blossomed into one of the NHL’s premier scorers on arguably the league’s best line.
Trade tree: Erat was shuffled off to the Coyotes at the 2014 trade deadline with F John Mitchell for F Chris Brown, D Rostislav Klesla and a fourth-round pick in 2015. The fourth-round pick was packaged with Jack Hillen to add defenseman Tim Gleason. He played 17 regular-season and 14 playoff games for the Caps in 2014-15, his final NHL campaign.
Klesla was quickly traded to the Sabres, along with goalie Michal Neuvirth, for goalie Jaroslav Halak and a third-round draft pick that ended up with the Rangers (selecting Robin Kovacs). Klesla refused to report to Buffalo and eventually ended up in Europe.
The deal: The Pittsburgh Penguins traded RW Markus Naslund to the Vancouver Canucks for RW Alek Stojanov on March 20, 1996.
In hindsight: Oh, this is painful. Stojanov would play 45 games with the Penguins, scoring two goals and four assists. Naslund would play 884 games with the Canucks, scoring 346 goals and 410 assists. He was a five-time All-Star and won the Pearson Award in 2002-03 as the NHL’s most outstanding player, as voted on by the NHLPA. At the time, the smart money was that Naslund wouldn’t become this player. He was 22 and wildly inconsistent, to the point that Canucks GM Pat Quinn said that Naslund “wasn’t a very good player” at the time of the trade. He was also expendable due to the Penguins’ glut of forwards.
Stojanov was seen as a power forward with potential, but injuries from a car accident in the 1996-97 season effectively capped that potential. So there were reasons for the trade to happen. That doesn’t change the fact that it was an epic whiff for Pittsburgh.
Trade tree: Neither player was traded again. Stojanov was out of the NHL after playing 35 games in 1996-97.