You often hear that a good trade is one that benefits both teams. Well, every general manager’s aim is to only make his team better, and sometimes they get an absolute steal in a trade. Usually these steals tend to happen when a team trades for a player who hasn’t reached his full potential yet, then enjoy that player’s prime years. It can also happen when a team trades an aging player who other teams feel still has something left.
Either way, the trades on this list tend to reflect that. For a player as legendary as Jaromir Jagr, it’s always going to be hard to get a fair return for him in a trade, but Jagr is on this list twice. That’s because in both instances, the team that traded him away essentially gave him up for nothing.
Moves like these usually come back to bite the losing GMs very quickly and it’s no surprise to see that many of the GMs who pulled the trigger on the losing side of these trades didn’t last much longer as a GM. To keep things in a modern perspective, we’re going to be sticking to the most one-sided NHL trades since 2000.
15. Stars Trade Pick no.28 (Corey Perry) For Two 2nd Rounders
This was a move that wasn’t thought of much at the time. Trading up and down for picks happens all the time on draft day. When the Ducks traded up in the 2003 draft to grab Corey Perry, they sent a pair of 2nd round picks to the Dallas Stars, who used those picks to take Vojtech Polak and B.J. Crombeen. Polak would only play in five NHL games, notching zero points, while Cromben would actually become a regular NHL player for a few seasons but only played 23 games with Dallas.
Meanwhile Corey Perry would become one of the best goalscorers in the league, even winning the Maurice Richard Trophy and the Hart Trophy in the 2010-11 season. He has been a cornerstone of the Ducks franchise for the past decade. Meanwhile the Stars struggled through much of the late 2000s before forming a nice core around Jamie Benn in recent years.
14. Islanders Dump Luongo For DiPietro
No, this wasn’t a Luongo for DiPietro swap, but that’s essentially what this trade was for. Mike Milbury had drafted Luongo fourth overall in the 1997 draft and was getting impatient with the young goaltender’s development. In 2000, the Islaners had the first overall pick and took DiPietro first overall, essentially giving the message that Luongo was not in their long-term plans. Shortly after drafting DiPietro, the Islanders traded Luongo and Olli Jokinen for Mark Parrish and Oleg Kvasha. Parrish would have some good seasons for the Islanders, including a 30-goal campaign in 2001-02. Still, the Panthers got themselves a franchise goalie and the Islanders got rid of one to make room for a draft bust.
Luongo was blindsided by the trade saying: “I didn’t expect it at all. One day they’re telling me I’m the goalie of the future, and the next day I’m gone. I didn’t really appreciate that. The good side is that [the Panthers] wanted me.”
13. Jaromir Jagr For Anson Carter
Anson Carter had some good seasons in the mid 2000s and was a good piece to have on your team, but come on, in what world is a one-for-one deal of Anson Carter for Jaromir Jagr fair? Not only was it a straight up trade, but the Capitals even agreed to pay $4 million of Jagr’s salary. The trade was made mostly because Washington was a little strapped for cash and the organization wasn’t having the kind of success they had hoped for when they pried Jagr from Pittsburgh a few years earlier. (We’ll get to that one)
Jagr went on to have a career resurgence in New York. Following the 2004-05 lockout, Jagr came storming out of the gate, recording 123 points. He would continue to be a point producer for the Rangers before leaving to play in Europe for a few years.
Carter would only play 19 games for the Caps before being flipped to L.A. for Jared Aulin just a couple of months later.
12. Rask For Raycroft
Much like the Luongo/DiPietro fiasco, the Leafs had a franchise goalie in their system, but saw a shiny new toy. Just one year after drafting Tuukka Rask, the Leafs traded him to the Boston Bruins to land Andrew Raycroft, who was coming off a disappointing sophomore season after winning the Calder Trophy in 2003-04. The Leafs made the trade because they felt Justin Pogge was their goaltender of the future, making Rask expendable. In the meantime, they felt maybe Raycroft could be their goalie of the present.
As it turned out, Raycroft never recaptured the magic of his rookie season in Boston, and he would never lead the Leafs to the playoffs. Pogge also turned out to be a dud for the Leafs.
Meanwhile, Rask shared the crease with Tim Thomas for several years, before eventually taking over as the team’s no.1 goalie, winning the Vezina Trophy in 2013-14. Oh, Toronto…
11. Alex Kovalev To The Canadiens For… Um….
Down the stretch in the 2003-04 season, Bob Gainey was trying to ensure his team would have some firepower to squeak into the postseason. Scoring was a major issue, as the Habs were too reliant on goaltender Jose Theodore. Near the ’04 deadline, Gainey would acquire Alex Kovalev from the Rangers in exchange for a 2nd round pick (Bruce Graham) and Jozef Balej. Balej would only play 13 games for the Rangers and was eentually out of the NHL by 2006. The pick of Bruce Graham didn’t amount to anything either for New York.
Kovalev would thrive in the Montreal spotlight. While he only had three points in the team’s final 12 regular season games, he would score 10 points in 11 playoff games. Kovalev would then become one of Montreal’s key contributors for several seasons His best season came in 2007-08, scoring 84 points and helping the Habs to a first place finish in the East.
10. Buffalo Pries Briere From Phoenix
Daniel Briere’s size kept the Coyotes from seeing his value as a player. He was drafted 24th overall in 1996 and didn’t make his NHL debut until 2000. However Briere’s work ethic would prove to be more valuable than his size, as he spent the 2001 offseason training with World’s Strongest Man Competitor Hugo Girard. The hard work paid off and Briere posted a 60-point season in 2001-02. So of course, the Coyotes traded Briere to Buffalo in 2003 with a 3rd round pick for Chris Gratton and a fourth rounder.
Following the lockout, Briere broke out in Buffalo, recording a 95-point season in 2006-08 and he would have several more productive years for the Flyers. He also proved to be a valuable playoff performer, recording 116 points in 124 career playoff games.
9. Jumbo Joe For Sturm, Primeau & Stuart
What is it with the Bruins and trading young talents away? Following the end of the lockout, the Bruins were growing frustrated with their lack of playoff success. Part of their beef was they felt their young captain Joe Thornton wasn’t a leader and was incapable of raising his level of play for the postseason. In November 2005, Thornton was having a productive season but the Bruins were struggling.
The Bruins traded their captain to the San Jose Sharks for Marco Sturm, Wayne Primeau and Brad Stuart. While the Bruins still ended up winning a Stanley Cup before the Sharks, you have to think Bruins fans would want this trade back. The Bruins likely would have had multiple Stanley Cups by now if they were bringing a 1-2 punch of Thornton and Bergeron down the middle.
Thornton has been one of the best playmakers of this generation and any way you look at it, this trade was a landslide.
8. Dan Boyle To San Jose For Matt Carle, Ty Wishart & Picks
Dan Boyle had been a key piece to the Tampa Bay Lightning’s Stanley Cup run in 2004, but following the lockout, the Lightning had a lot of trouble replicating that success. Boyle was having injury problems and on July 4, 2008 he was traded to San Jose along with Brad Lukowich for Matt Carle, Ty Wishart and a first-round pick in 2009, as well as a fourth rounder. Boyle agreed to waive his no-trade clause, due to the fact that he knew Joe Thornton, Patrick Marleau and Evgeni Nabokov.
Boyle would have his prime seasons with the Sharks, immediately becoming the team’s leading scoring defenceman. The Sharks were a consistent playoff team throughout the late 2000s and into the 2010s. While the Sharks haven’t been able to win a Stanley Cup, they weren’t cellar dwellers, unlike the Lightning, who had to go through some tough years to get to their present state.
7. Ryan McDonagh For Scott Gomez
There were a lot of pieces in this trade, but Habs fans only view it as McDonagh for Gomez. McDonagh was a first round pick in the 2007 draft, a draft in which the Habs’ amateur scouting staff hit home run after home run, drafting McDonagh, Max Pacioretty and P.K. Subban with their first three picks.
Following a disappointing centennial season, GM Bob Gainey felt the need to shake up his team. He sent his top defensive prospect McDonagh, along with Chris Higgins, Pavel Valentenko and Doug Janik to the Rangers for Scott Gomez, Tom Pyatt and Michael Busto.
This trade was a complete landslide, as the Rangers were happy to get rid of Gomez’s eight-year, $56 million contract. Gomez’s decline continued in Montreal, while McDonagh made the Rangers roster shortly after this trade and is now their captain.
Throught the early 2010s, fans in Montreal were pained, realizing the team could have had a top pairing of McDonagh and P.K. Subban. The trade hurt the most when McDonagh’s Rangers knocked off the Canadiens in the 2014 Eastern Conference Final, with McDonagh being the best skater in the series.
6. Chris Pronger To Anaheim For Joffrey Lupul, Ladislav Smid and 2 Draft Picks
The Ducks lucked into this one, as Chris Pronger asked for a trade from Edmonton shortly after signing a long-term extension. The Oilers were in a bit of a tough spot, so all they got for Pronger was Joffrey Lupul, Ladislav Smid and two draft picks. Pronger would pay immediate dividends for the Ducks, as he led the team to the Stanley Cup in the following season (2006-07). The Oilers meanwhile got an injury prone Lupul, and the best piece they got in the deal was a first round pick, which they used to acquire Jordan Eberle.
Still, the fact that the Oilers’ blueline was a mess for a decade and they didn’t make the playoffs, while the Ducks got the missing piece for a Stanley Cup run, makes this one a landslide.
5. Flyers Let Patrick Sharp Slip To Chicago
When people think of Patrick Sharp, they think of him as a Chicago Blackhawk, having served a key role in the three Chicago Stanley Cup wins (2010, 2013, 2015). Sharp was an alternate captain in Chicago and was a valuable scoring winger, often saving his best stuff for the playoffs. He’s now proven to be a valuable piece to the Dallas Stars.
Many people forget though, that Sharp was originally a Philadelphia Flyer. Sharp was taken 95th overall in the 2001 draft. Not many 5th round picks ever make the NHL, but Sharp became a regular for the Flyers late in the 2003-04 season. After injury problems and struggling to find his scoring touch, Sharp was traded along with Eric Meloche to Chicago for Matt Ellison and a third round pick.
Sharp was another piece of the puzzle for the Blackhawks, who would defeat the Flyers in the Stanley Cup Final four years after this trade.
4. Roberto Luongo For Alex Auld, Todd Bertuzzi and Bryan Allen
What is it with Luongo being traded for sub-par pieces? After the Florida Panthers stunk up the joint through half of the 2000s, constantly leaving their goalie out to dry, maybe GM Mike Keenan was just giving Luongo a break. Prior to the 2006-07 season, the Panthers traded Luongo to Vancouver along with Lukas Krajicek and a 6th rounder for Todd Bertuzzi, Bryan Allen and Alex Auld. Luongo again was surprised by being traded, saying he felt he and the Panthers were closing in on a contract extension.
Prior to Luongo’s arrival, 18 different starting goaltenders had taken the crease for the Canucks in seven and a half years. Luongo would be the franchsie goalie the Canucks had been craving for so long. While Luongo and the Canucks had their ups and downs, there’s no doubt they swindled the Panthers on this trade.
3. Tyler Seguin For Three Years Of Loui Eriksson
Following the Bruins’ loss in the 2013 Stanley Cup Final, word had begun to spread that the team was unhappy with their young star Tyler Seguin. They felt the 2010 second overall pick was immature and weren’t too keen on his partying ways.
While I would have included the Phil Kessel for two first round picks trade in this list, due to Seguin being one of those picks, the Bruins didn’t really capitalize on that, so we’ll go with this one. Seguin was traded to Dallas in the 2013 summer, along with Rich Peverley and Ryan Button for Loui Eriksson, Reilly Smith, Matt Fraser and Joe Morrow. The most valuable piece Boston got was Eriksson, who had some great years in Boston, but has since left in free agency.
Seguin has emerged as a star in Dallas, a prime offensive threat and he will be a key piece to the Stars for years to come.
2. Jaromir Jagr To Washington For Scraps
It’s hard to think the Penguins couldn’t find a better deal than this one for someone who had been a face of their franchise for so many years. There was reported friction between Penguins superstars Mario Lemieux and Jaromir Jagr, following Lemieux’s career comeback in 2001, and Jagr’s scoring touch seemd to take a dip.
The cash-strapped Penguins also were having trouble paying both superstars’ salaries, so in the summer of 2001, they sent Jagr, along with Frantisek Kucera to Washington for Kris Beech, Michal Sivek and Ross Lupaschuk.
Jagr’s numbers dipped in Washington, but it sure was better than anything the Pens got from this trade. Again, this was more of a case where it felt like the Pens should have gotten a lot more for someone who had been a superstar in the NHL for so long.
1. Milbury Dumps Chara and Spezza For Alexei Yashin
If anyone knows how to dismantle a team in one day, it’s Mike Milbury. Having already traded several key young pieces of the Islanders away, he pulled off perhaps his worst move as a GM on draft day in 2001. That day, Milbury had the second overall pick, which could have been used to draft Jason Spezza to add to a core being headed by Zdeno Chara. Instead, Milbury traded the towering Chara away to Ottawa, along with the second overall pick and Bill Muckalt for Alexei Yashin.
Spezza would go on to be the Sens’ no.1 center, Chara would go on to be one of the most dominant defenceman of this generation and Yashin would prove to be an organizational cancer for the Islanders. His point production declined and he never lived up to his big contract.
There’s no doubt this trade helped sink the Islanders and saw them become a running joke of the 2000s.
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