All four of North America’s major sports leagues have one thing in common. Teams are always looking to make that key move in hopes of finding the “secret sauce” to a championship.

The NHL, with its modern day salary cap, has seen plenty of wheeling and dealing in order to keep teams competitive — and solvent.

Trades are made and rosters are molded with the hope that their team will be a force to be reckoned with, whether now or later. Some personnel moves result in immediate success, as teams go on to win championships and make management look like geniuses.

The transactions that are made to create financial stability can also make a club look good, if they keep winning. But for every fiscal success, there are penny-pinching moves that are seen by fans as wrong-headed, cynical and fickle.

The worst of the deals leave fans, pundits and even adversaries wondering what management was even thinking. Like “Couldn’t they come up with something better than that?”

Listed below are 20 NHL transactions, in no particular order, that have left one team with gems and the other team with fool’s gold in return.

20. Maple Leafs Ship Russ Courtnall to the Habs

Toronto Maple Leafs trade Russ Courtnall to the Montreal Canadiens for John Kordic and a sixth-round draft pick on November 7, 1988

This trade was dreadful for the Blue and White. Former Leafs GM Gord Stellick, wanting more toughness out of Courtnall (who had two points nine games into the 1988-89 season) swung the worst deal in Leafs history. He traded the speedy Courtnall for Montreal Canadiens’ noted pugilist John Kordic. Over a nine year career, Kordic accumulated only 35 points and in 1992 after failed stints with the Quebec Nordiques and Washington Capitals the 27-year old Kordic tragically died after a drug overdose.

Courtnall, on the other hand, quickly became a fan favorite with his speed and skill, scoring 22 goals and 39 points over the remaining 64 games of the 88-89 campaign. He played a total of 250 games with the Bleu, Blanc et Rouge and had 195 points. Over his 19-year career the native of Duncan B.C. tallied a respectable 744 points in 1,099 games. Stellick, then the youngest GM ever at 30, resigned after the 88-89 season, after disputes with crotchety and meddling old owner Harold Ballard.

(CP PHOTO/Bill Grimshaw)

19. Oilers Deal Miroslav Satan To Sabres

Edmonton Oilers trade Miroslav Satan to the Buffalo Sabres for Barrie Moore and Craig Millar on March 18, 1997

Former Oilers GM Glen Sather would love to have a do over on this transaction with Buffalo. After the dynasty years, the Oilers ran into some financial woes and questions were asked about whether hockey could survive in Edmonton. It could be suggested that this transaction was made to shed payroll and have some financial flexibility. At the time of the swap, a young Satan had 63 points in 126 games (20 on the powerplay).

In Buffalo, Satan blossomed and would hit a high of 75 points in 79 games during the 2002-03 season. He would go on to play 1,050 total career games with Edmonton, Buffalo, New York Islanders, Pittsburgh, and Boston. He also skated in the Winter Olympics four times, twice in the World Cup of Hockey, and multiple times at the World Hockey Championships. As for the players going the other way, Moore lasted four games in a Oilers uniform (0 points) and would play just one more NHL game. Millar lasted a little longer, donning Edmonton colors for 36 games over parts of three seasons and scoring six points.

(CP PHOTO/Kevin Frayer)

18. Flames Trade the Golden Brett to St. Louis

Calgary Flames trade Brett Hull and Steve Bozek to the St. Louis Blues for Rob Ramage and Rick Wamsley on March 7, 1988

Drafted 117th by Calgary in 1984, Brett Hull had a tough time with Flames management and coaches early on, taking flak for being out of shape. Thus, after just 57 games in a Flames uniform, but logging a respectable 51 points, Calgary swung him and journeyman Steve Bozek to St. Louis for Rob Ramage and goalie Rick Wamsley. Hull’s career took off in the Gateway City, where he would tally over 70 goals in a season three times and snipe 527 total goals in 744 games with the Blues. Over his brilliant career, with five different teams, he would win two Stanley Cups, make eight All-Star Game appearances and win the Hart and Lady Byng Trophies.

Veteran defenceman Ramage saw action in 80 games for Calgary and won a Stanley Cup before moving on to Toronto for the 1989-90 season. Wamsley would hang around until the 1991-92 season, also winning a Cup with Ramage in 1989. He was strictly back-up material to Mike Vernon and posted a 53-30-15 record with a pedestrian goals against average of 3.21 and save percentage of .878. The Flames could only imagine after: “what if?”

(AP Photo/Tim Fitzgerald)

17. Bobby Lu Goes to Florida (The First Time)

New York Islanders trade Roberto Luongo and Olli Jokinen to the Florida Panthers for Oleg Kvasha and Mark Parrish on June 24, 2000

Former Islanders GM Mike Milbury was an all or nothing guy, making some decent — and some dubious — trades. One of his more famous blunders was dealing a young Roberto Luongo to the Florida Panthers, along with promising young forward Olli Jokinen for what would amount to spare parts. So, at the 2000 amateur draft, Milbury sent the Panthers future All-Stars for forwards Oleg Kvasha and Mark Parrish. Bobby Lu’s first spin with Florida (he is there again and rocking it) resulted in a second team All-Star nomination as well as consideration for the Vezina in two of his five seasons. Jokinen turned into a reliable scorer in south Florida, recording 419 points in 567 games.

Unfortunately for the Islanders, Parrish would be the best of the return, appearing in 345 games and scoring 214 points, with a -34. Kvasha was decent but never really became the player Milbury thought he would, playing in 332 games and registering 156 points. So, not only did Florida get more production out of the swap (Jokinen would outscore Kvasha and Parrish 419 to 370), they also received top shelf netminding.

Source: Sbnation.com

16. Penguins Deal Markus Naslund to Vancouver

Pittsburgh Penguins trade Markus Naslund to the Vancouver Canucks for Alek Stojanov on March 20, 1996

Hindsight is always 20/20 but the transaction the Pittsburgh Penguins made in 1996 with Vancouver was just plain myopic. Markus Naslund, who was drafted in the first round (16th overall) of the 1991 draft, started slowly in his NHL career in Pittsburgh but by the first part of the 1995-96 campaign, he had worked his way onto the first line, scoring 36 points in 29 games. However, his production tailed off later and instead of preaching patience with him, they flipped him to Vancouver late in the season for 1991 seventh overall pick Alek Stojanov, who had all of one assist in 62 games for the Canucks.

Naslund would end up playing 1,117 career games (884 with Vancouver), registering 867 points and being a first team All-Star three times. Naslund was captain for most of his time in B.C. and was also a force on the international ice for Team Sweden. Stojanov would be a footnote to one of the most lopsided trades ever made, skating in 45 total games in Pittsburgh, with two goals and four assists. Stojanov would be a career minor leaguer and retire in 2002 at the age of 29.

(CP PHOTO/Richard Lam)

15. Islanders Swap Zdeno Chara for Alexei Yashin

New York Islanders trade Zdeno Chara, Bill Muckalt and 2001 1st round pick (Jason Spezza) to Ottawa Senators for Alexei Yashin on June 23, 2001

As if the 2000 trade that sent Roberto Luongo to Florida wasn’t bad enough, Mike Milbury cemented his name in the executive Hall of Shame with a worse deal at the 2001 entry draft. Looking for scoring to build a contender, Milbury coveted Ottawa’s Alexei Yashin, who had 491 points in 504 games but was expensive and didn’t endear himself to Ottawa fans. Well, after he shipped future all-world defenceman Zdeno Chara, along with Bill Muckalt and a 2001 first rounder to Ottawa, it could be argued that this deal effectively ended his career.

Trading Yashin turned out to be fiscally responsible as well as outstanding player personnel wise for Ottawa, as the first round pick turned into Spezza, who led the team to the Stanley Cup Finals in 2007, before losing against Anaheim. Chara developed into the snarly, minute-eating defenceman he has been for the Boston Bruins in recent years, scoring 146 points in 299 games along with 554 penalty minutes. He also finished second in Norris Trophy voting during the 2003-04 season. Milbury would gum up the works by throwing a massive 10-year, $87.5 million contract at Yashin, who became a regressive distraction on Long Island for just five campaigns. Fully 10 years after Yashin packed in his NHL career, both Chara and Spezza are still playing.

(CP Fred Chartrand)

14. Leafs Send Tuukka Rask’s Rights to Boston For Andrew Raycroft

Toronto Maple Leafs trades the rights to Tuukka Rask to Boston Bruins for Andrew Raycroft on June 24, 2006

Former Leafs GM John Ferguson Jr’s tenure with Toronto was short, brutal and steeped in controversy. It didn’t help that owner Maple Leaf Sports and Entertainment (MLSE) held Ferguson hostage with a “make the playoffs or else” attitude, either. After a disappointing 2005-06 season, the Leafs were looking for a capable goalie to replace the aging Ed Belfour. Ferguson Jr., who was taking flak for the firing of popular coach and former GM Pat Quinn, saw former 2003-04 Calder Trophy winner Raycroft as the answer. Only problem was, there were more questions about his play post 2004-05 lockout, as he logged a miserable 3.71 goals against average and .879 save percentage in just 30 games.

In a move seen as a career killer, Ferguson Jr. swapped 2005 first round pick (21st overall) Tuukka Rask to Boston for Raycroft. Rask would go on to win  Stanley Cup ring with Boston in the spring of 2011 as well as a Vezina Trophy in 2013-14. Raycroft wasn’t bad during his first season in Toronto, but after 19 games played during the 2007-08 season and lousy 3.92 GAA and .876 save percentage, he was waived and bought out of his contract.

THE CANADIAN PRESS/Adrian Wyld

13. Patrick Roy Breaks Up With Montreal

Montreal Canadiens trade Patrick Roy and Mike Keane to Colorado Avalanche for Jocelyn Thibault, Martin Rucinsky and Andre Kovalenko on December 6, 1995

The date December 2, 1995 will live on in infamy for Habs fans and Patrick Roy. It was known that the three-time Vezina Trophy and two-time Stanley Cup winner had a rocky relationship with former head coach Mario Tremblay long before the fateful game played against Detroit that night. The Wings blew into town that day and massacred the Habs 11-1, with Roy giving up nine goals on 26 shots. Star goalies are typically pulled if they are having an off night but Tremblay, no doubt wanting to embarrass his vocal goalie, left him in the game. Eventually Roy was pulled but on his way to the end of the bench he told Tremblay and team president Ronald Corey, “It’s my last game in Montreal!”

Four days later he was dealt to Colorado, where would remain a Vezina candidate for many years and win two more Stanley Cups in his illustrious Hall of Fame career. The players Montreal got back weren’t chopped liver, but it must be said that Montreal hasn’t won a Cup since 1993, which means there might be a curse of St. Patrick upon them.

(AP Photo/David Zalubowski)

12. Leafs Miss Out On A Legend At 1991 Entry Draft

Toronto Maple Leafs trades their first round pick (3rd overall – Scott Niedermayer) to the New Jersey Devils for Tom Kurvers on October 16, 1989

If there was a trophy for knee-jerk, bone-headed trades, the Leafs would be all-time. It’s fitting, in a way, that former Leafs GM Floyd Smith put the finishing touches on the deplorable 1980’s by trading for high-scoring, riverboat gambler defenceman Tom Kurvers’ early in the 1989 season. He was just coming off a career high 66-point season with New Jersey but was made available early in the 89-90 season. The Leafs bit, dealing their first pick (which was a them in Leaf Land until recently) in the 1991 draft for the veteran D-man.

Kurvers recorded 52 points that season for the Buds, but his defensive flaws showed the next season and after thee points in 19 games and a -12, he was traded to Vancouver. New Jersey would use that first pick to select Scott Niedermayer. Instead of toiling in Toronto, he would win a Norris Trophy, three First Team All-Star nods, a Conn Smythe Trophy, four Stanley Cups, as well as two Gold medals at the Winter Olympics with Team Canada. Niedermayer’s legacy was cemented with enshrinement at the Hockey Hall of Fame in Toronto.

(AP Photo/Mark Avery, File)

11. “The Trade”

Edmonton Oilers trade Wayne Gretzky, Mike Krushelynski and Marty McSorley to the Los Angeles Kings for Jimmy Carson, Martin Gelinas, three 1st round picks as well as $15 million on August 9, 1988

This trade that shook the NHL to its core and brought hockey to the American south west — and ended a dynastic run — was orchestrated by Oilers owner Peter Pocklington, who forever seemed to struggle financially. Two hours after winning his fourth Stanley Cup in 1988, Gretzky learned that the team was planning to deal him. He didn’t want to leave Edmonton, but was informed during his honeymoon, he was notified that he had been dealt to Los Angeles in a massive multi-player trade.

The Great One wouldn’t win another title with L.A. but still won three more scoring titles and another Hart Trophy with the Kings. While the deal wasn’t that lopsided, it did make a pariah out of Pocklington, who broke up a ridiculously talented core in the name of the almighty dollar. The Oilers would win another Stanley Cup in 1990, but haven’t won it all since.

Source: Sportsnet.ca

10. Coyotes Send Daniel Briere To Buffalo

The Phoenix Coyotes Trade Daniel Briere and a 2004 third round pick for Buffalo’s Chris Gratton and a fourth round selection

The old Winnipeg Jets (turned Phoenix/Arizona Coyotes) are still looking for that elusive first Stanley Cup. Well, trades like the one that involved Daniel Briere going to Buffalo with a third round pick for veteran playmaker/tough guy Chris Gratton at the deadline in 2003 didn’t — and won’t — get the ‘Yotes any closer. Originally drafted in 1996 (24th overall) Briere used a rigorous off-season training regimen in 2001 to have a career year, scoring 60 points in 78 games during the 01-02 season.

But, at the 2003 deadline, Briere, who had 46 points in 68 games, was packaged up with the pick for Gratton, who was already a veteran of over 500 games and had 44 points and 86 PIM in 68 games. So, the optics said it was a wash. That is, until Briere more than lived up to his promise with the Sabres, eventually scoring a career high 95 points in his third and last season (2006-07). Gratton, for his part, was not as robust a presence in Phoenix as he was previously, mustering just 30 points and 114 PIM in 80 games, along with a -30 before being traded to Colorado.

(AP Photo/David Duprey)

9. Edmonton’s Chris Pronger Forces Trade To Anaheim

Edmonton Trades Chris Pronger To Anaheim For Joffrey Lupul, Ladislav Smid, two first round picks and a second rounder on July 3, 2006

This awful deal was as much about Chris Pronger being disgruntled in Edmonton — despite gladly signing a lucrative five year contract the year previous — as it was about the ho-hum return the Oilers got for the premier rearguard. Pronger, former Norris winner in St. Louis, had a Norris worthy season for Edmonton in 2005-06, scoring 56 points in 80 games. He also played a huge role in the Oilers making a long awaited Stanley Cup final in ’06, recording 21 points in 24 games while playing almost 31 minutes per game.

Despite that success, it was rumored that Pronger’s wife chafed at being in a cold, wintry place and that he had requested a trade. GM Kevin Lowe acquiesced and the rumors limited his bargaining power. In exchange for a Norris winner who would help the Ducks win a championship in 2007, the Oilers got one tepid year from Lupul (28 points, -29 in 81 games) and parts of eight seasons out of Smid, who would never be mistaken for an elite defenceman. It wasn’t a total loss, as one of the first round picks did turn into Jordan Eberle.

(AP Photo/Paul Sakuma)

8. Philadelphia Deals Patrick Sharp To Chicago

The Philadelphia Flyers trade Patrick Sharp and Eric Meloche to the Chicago Blackhawks for Matt Ellison and a third round draft pick on Dec. 5, 2005

The Law of Diminishing Returns sure came back to bit the Philadelphia Flyers in late 2005. They had former NCAA star Patrick Sharp in their line-up, but couldn’t see his potential. By the early part of the 2005-06 season, Sharp had 10 goals and 15 points in 66 games, which probably weren’t the numbers Philly was expecting out of him. With little fanfare, then, the Flyers flipped him and Eric Meloche to Chicago for Matt Ellison and a third round pick.

Funny how players blossom in the right situations, while others flounder. Sharp fluorished in Chicago and by the 2009-10 season, he had 66 points in 82 games. Ironically, too, he tallied 22 points in 22 playoff games, helping the Hawks beat Philadelphia in the 2010 final. He had four of his 11 goals and two of his 11 assists against the Flyers, just to put a dagger in the team’s heart. Ellison, who had 12 points in 26 games for Chicago before the trade, ended up appearing in just seven more NHL games, all with the Flyers, registering an assist.

(AP Photo/Matt Slocum)

7. Atlanta Thrashers Deal Ilya Kovalchuk To The New Jersey Devils

The Atlanta Thrashers trade Ilya Kovalchuk and Anssi Salmela to New Jersey for Johnny Oduya, Niclas Bergors, Patrice Cormier and a 2010 First Round Selection

Just like the old Winnipeg Jets/Arizona Coyotes, the new Winnipeg Jets/Atlanta Thrashers are searching for their first NHL championship. And, not agreeing to salary demands of uber-talented players like Kovalchuk cut right to the heart of playoff disappointment. In his first eight seasons in the league with the fledgling Thrashers, Kovalchuk was “the man”, scoring over 50 goals twice and 328 times total in 594 games. Yet, the Thrashers made it to the playoffs just once, where Kovalchuk scored a goal and an assist in four games of the 2007 post-season.

During the 2009-10 season, a contract dispute for the soon-to-be free agent was brewing and instead of losing him for nothing Atlanta GM Don Waddell packaged him up with Anssi Salmela to the Devils for Johnny Oduya, young forwards Bergfors and Cormier and a 2010 first rounder. Kovy eventually led the Devils to the 2012 Stanley Cup finals, where he had 19 points in 23 games (he had played just nine post-season games previous). Oduya, who has won two Cups since that deal, didn’t hang around long enough to make an impact, while Bergfors (79 games, 46 points) and Cormier (52 games with Atlanta/Winnipeg) made minimal contributions.

(AP Photo/Jason DeCrow, File)

6. San Jose Sharks Flip Josh Gorges To Montreal

San Jose Sharks Trade Josh Gorges and 2007 first round pick to Montreal for Craig Rivet and 2008 fifth round pick on Feb. 25, 2007

Josh Gorges has never been a prolific scorer from the blue line, nor a particularly punishing rearguard, but he has been a solid top four guy who did a lot of little things well, like block shots and play against other teams top lines. The Sharks actually signed him as an undrafted free agent out of junior hockey but after he made the team, he struggled when being given extra ice time. The decision at the time, then, was easy enough to include him in a deal that also packaged up a first round pick to Montreal for veteran defenceman Craig Rivet and a 2008 first rounder.

Gorges would be a boon to the Montreal blue line, playing 464 games in eight years, with 88 points and a +34. Rivet wasn’t bad on the Sharks blue line, but stayed in the Bay Area for just 91 games (43 points). It was the future players included in the trade that gave Montreal the provisional edge in this one. The first round pick turned into current captain Max Pacioretty, who has 429 points in 523 games. The fifth round the Sharks received was used on useful defenceman Jason Demers, who got in 300 games with San Jose, scoring 98 points and logging a +20.

(AP Photo/Bill Boyce, File)

5. Montreal Swaps Ryan McDonagh To The New York Rangers

Montreal Canadiens trade the rights to Ryan McDonagh, along with Chris Higgins, Pavel Valentenko and Doug Janik to the New York Rangers for Scott Gomez, Tom Pyatt and Michael Busto on June 30, 2009.

While Montreal fleeced San Jose a bit with the 2007 trade that brought in Josh Gorges, they lost a better blueliner in Ryan McDonagh before he even played a game with them. Drafted 12th overall in 2007 (the same year of the Gorges trade), McDonagh’s rights were dealt, along with Chris Higgins, Pavel Valentenko and Doug Janik to the New York Rangers for Scott Gomez, Tom Pyatt and Michael Busto.

Since joining the Blueshirts for the 2010-11 season, McDonagh has been nothing but a steady first pair defenceman who also happens to be the team’s captain. To date he has 227 points in 493 games and is +141. None of the other players headed to the Big Apple had a great impact, but McDonagh alone turned into a steal. Gomez, pivotal to getting the four players from Montreal, had one decent season and then played his way out of Montreal. He finished with 108 points in 196 games, well below his average.

(AP Photo/Gerry Broome)

4. Marian Hossa Sent To Pittsburgh

Atlanta Trades Marian Hossa and Pascal Dupuis for Colby Armstrong, Erik Christensen, Angelo Esposito and a first round pick on Feb. 26, 2008

Hossa would only be a rental with the Penguins in 2008, but his small part went a long, long way. A regular season offensive force who scored a career high 100 points for the Thrashers in 2006-07, Hossa was in a contract year and with an extension not forthcoming, management decided to trade him rather than lose him. The six-player swap with Pittsburgh also included journeyman winger Pascal Dupuis.

As it turned out, Hossa, who was not known for playoff success, scored 26 points in 20 games as the Pens fell to Detroit in the finals. Dupuis chipped in seven points and threw 42 checks during the post-season. He would win the title with Pittsburgh the following season. Hossa stayed only for that partial season and coincidentally signed with Detroit, who lost to the Pens the next year. Of the players Atlanta received, only Armstrong would have middling success, registering 80 points in 179 games.

THE CANADIAN PRESS/Sean Kilpatrick

3. Lightning Part With Cup Winner Dan Boyle

Tampa Bay Trades Dan Boyle and Brad Lukowich to San Jose for Ty Wishart, Matt Carle, a first round and a fourth round pick on July 4, 2008

The inevitable tear down of the 2004 Stanley Cup champion Tampa Bay Lightning was inevitable, however, good to great players like Dan Boyle had to be tough to part with. For six seasons starting in 2001-02, Boyle was a rock for the Bolts, playing in 394 games and recording 253 points (126 on the powerplay). He was also invaluable in their Stanley Cup run in 2004, scoring two goals and eight assists in 23 games and going +7. He was great for two more seasons, but suffered a freak injury in 2007 and played in just 37 games (25 points) during the 07-08 campaign. However he did sign a six-year contract extension, but was traded anyway on July 4, 2008 along with Brad Lukowich to San Jose for Ty Wishart, Matt Carle, a first round and a fourth round pick.

Boyle would recover from his freak injury well enough to star for six seasons in San Jose, registering 269 points in 431 games, as well as another 48 points in 62 playoff contests. Wishart played all of five games with Tampa Bay, while Carle was with the Lightning for 12 games before being traded again early in the 2008-09 season. While Carle would later play for the Lightning again, Tampa got hosed on this deal, as neither of the draft picks turned into anything either.

THE CANADIAN PRESS/Darryl Dyck

2. Dallas Deals James Neal To Pittsburgh

Dallas Stars Trade James Neal and Matt Niskanen to the Pittsburgh Penguins for Alex Goligoski on Feb. 21, 2011

For eight years, former Penguins GM Ray Shero made astute deals that set the foundation for championships in Pittsburgh. Some would say he absolutely bamboozled some of his peers in swaps from 2006 to 2014. One such deal involved young Dallas Stars sniper James Neal, who he wrangled along with fellow young blueliner Matt Niskanen, for D Alex Goligoski.

Neal didn’t crack the 30-goal barrier in three years with Big D, but after a relatively slow start in Pittsburgh, scored a career high 40, along with 41 assists during the 2011-12 season. In all, Neal notched 184 points in 195 games in a Pens uniform, as well as 22 points in 38 playoff contests. Niskanen blossomed too, registering a career best 46 points during the 2013-14 season. Goligoski was decent as the return on Neal and Niskanen, however, he wasn’t any more productive than Carle on a per-game basis, giving Pittsburgh a big win on this trade.

(AP Photo/Don Wright)

1. Columbus Swaps Jakub Voracek to Philadelphia

Columbus Blue Jackets trade Jakub Voracek and two 2011 draft picks (first and third rounder) to Philadelphia for Jeff Carter on June 23, 2011

In terms of overall impact, this is one of the most lopsided trades on this list. When Columbus swung young playmaker Jakub Voracek for veteran Jeff Carter from Philadelphia, it was thought the Blue Jackets got the better of the trade. Now, Carter went on to revive his career in L.A., but had a negligible impact on Columbus.

What made the June 2011 deal worse for Columbus was the fact that they included a 2011 first round pick that turned into Sean Couturier and a 2011 third rounder (Nick Cousins). To date, Voracek is a first liner who has 391 points in 475 games. Couturier is a premier two-way player who has notched 221 points and a +48 in 446 games, while defenceman Cousins contributed 27 points in 107 contests over three seasons. Carter scored 25 points in 39 points before being traded again during the 2011-12 season.

(AP Photo/Matt Slocum)