The NHL season runs from the start of October to the Stanley Cup Finals in June, but it is the four months of off-season in which teams are constructed and front office jobs are both won and lost. From the NHL Draft through to free agency, general managers use the summer months to shape the future of their club - for better or worse. Success at the draft helps create a blueprint for what is, ostensibly, the long-term vision for a franchise, while free agency serves as a tool for fast-tracking improvement through the addition of veterans who are ready to contribute immediately. In the midst of all of that is the trade market, where clubs look to other rosters in hopes that there is a shared interest in swapping assets coveted by one another. Of course, it can all go so wrong. Drafts have busts, free agency brings disappointing players who fail to live up to their big salaries and trades have the ever-present chance to blow up as you wind up shipping out more value than you bring back in.
Now, trades obviously aren't limited to the summer, as action can typically build right up to the late season trade deadline. But with many teams reluctant to retool on the fly while still playing games and up against league-imposed deadlines, June to October is when the majority of the action happens. We could focus on some of the best moves that helped propel teams to Stanley Cup glory, but let's be honest here - it's a lot more fun to look at the ones that flamed out spectacularly. From draft busts to colossal free agent mistakes to lop-sided trade losses, here are 25 painfully stupid off-season moves that should have gotten the executives that made them fired (including a few that probably did).
25 Alexei Yashin (New York Islanders)
While those of a certain age probably remember Mike Milbury best for jumping into the stands at MSG and beating a fan with his own shoe, long-suffering Islanders fans of more recent times probably recall a spotty trade record that prompted his "Mad" Mike nickname. His 11-year tenure as the club's GM brought a litany of ill-advised trades, costly free agent signings and draft fails.
When it came to Alexei Yashin, Mad Mike covered each of the first two categories. Milbury found himself so enamored with the two-time 40-goal scorer that he was willing to surrender the No. 2 over-all pick, which Ottawa used on Jason Spezza, and a tall, young defenseman by the name of Zdeno Chara. Soon after the trade, Milbury awarded Yashin with a 10-year, $87.5 million contract that quickly became an albatross.
24 Jeff Finger (Toronto Maple Leafs)
From the outset of this list, its necessary to acknowledge the fundamental unfairness in evaluating each of these deals so far after the fact. Most of these transactions looked reasonable and sometimes even excited a fan base prior to flaming out spectacularly. The Toronto Maple Leafs' 2008 free agent signing of Jeff Finger wasn't one of those moves.
When GM Cliff Fletcher signed the 27-year-old Avs blue liner to a four-year, $14 million contract on the first day of free agency, the immediate reactions were 'who?' and 'how much money?' Fletcher and the Leafs tried to sell fans on Finger being an unheralded stalwart who was poised to thrive in the spotlight. Instead, he'd be out of the NHL within two years and finish out his contract in the minors.
23 Bobby Ryan (Ottawa Senators)
Rarely does a 26-year-old sniper with four 30-goal seasons under his belt show up on the trade market, so it made perfect sense that the Ottawa Senators jumped on the chance to acquire Bobby Ryan from Anaheim. The Ducks saw the writing on the wall with Ryan closing in on free agency and turned him into a trio of young assets that included Jakob Silfverberg and Nick Ritchie.
The Sens, meanwhile, figured they were getting a bona fide scorer just entering his prime, and paid him accordingly. They made what seemed to be a safe gamble by handing Ryan a seven-year, $50.75 million extension. Since then, however, the player drafted after Sidney Crosby hasn't come as advertised, failing to pot more than 23 goals in any season in Ottawa. A strong playoff run last spring offered encouragement, but the five years and $37 million left on his deal looks daunting.
22 Jeff Carter (Columbus Blue Jackets)
For much of their existence, the Columbus Blue Jackets have played it safe, resisting temptations to go all-in on a star player. Since joining the league in 2000, that strategy has earned them precisely zero playoff series wins and three postseason victories. That's why it was refreshing in 2011 to see them take a gamble and make a push for Jeff Carter, a 26-year-old sniper who had averaged 38 goals over the previous three years with the Flyers.
Sidelined with a broken foot to start the 2011-12 season, Carter never really got going for the Jackets, scoring just 11 goals in 39 games. As if to mitigate their mistake, Columbus quickly turned around and dealt him to Los Angeles before season's end. In exchange for those 39 games of Carter, the club surrendered Jakub Voracek, Sean Couturier and Nick Cousins. Carter won 2 Stanley Cups with Los Angeles.
21 Jean-Sebastien Giguere (Calgary Flames)
Ahead of the 2000-01 season, teams were also preparing their roster to withstand the effects of an Expansion Draft that was bringing Columbus and Minnesota into the league. As such, Calgary had to sort out a goaltending situation that featured veterans Mike Vernon and Fred Brathwaite sharing duties while prospect Jean-Sebastien Giguere waited in the wings.
By opting to trade Giguere to Anaheim in what was his first deal as the club's GM, Craig Button gifted the Mighty Ducks with the goalie who would earn Conn Smythe honors as playoff MVP for the 2003 postseason. Though Anaheim fell one game short of Stanley Cup glory that year, Giguere would backstop the team to the Cup four years later. The Flames, meanwhile, have been searching for a reliable netminder seemingly ever since.
20 Uwe Krupp (Detroit Red Wings)
Known as a gritty, hard-nosed defender during a decorated stint with the Colorado Avalanche, the Detroit Red Wings knew that an established stalwart on the blue line could boost their Stanley Cup chances. So in 1998, they valued Krupp's toughness to the tune of a four-year, $16.4 million contract. Barely over a year into the deal, however, Krupp had spent more time battling injuries and his own organization than opponents.
After suffering from a herniated disc in his back, Krupp was found dog-sledding, prompting Detroit to attempt to void his contract. This resulted in nearly two years of legal battles before the German standout ultimately made a brief return to the lineup. When the Red Wings won the Cup again in 2002, Krupp did not get his name etched alongside his teammates on account of not playing enough games.
19 Todd Bertuzzi (Florida Panthers)
The 2006 blockbuster trade between the Vancouver Canucks and Florida Panthers was a case of swapping out unwanted parts. The Canucks acknowledged that star forward Todd Bertuzzi was in need of a change of scenery after facing a year-long suspension and criminal charges owing to his on-ice attack that ended the career of Steve Moore. Meanwhile, the Panthers wanted to avoid losing goalie Roberto Luongo for nothing in free agency.
One of the clubs got what they wanted. Back spasms limited Bertuzzi to just seven games before opting for surgery, during which time Florida shipped him to Detroit. Going the other way, Luongo became a fixture in Vancouver, leading the Canucks to six playoff appearances, including the 2011 Stanley Cup Finals. With his prime years behind him, Luongo has since made his way back to the Sunshine State.
18 Thrashers 1st Overall Pick (1999 NHL Draft)
Arguably the worst NHL Draft class ever, the 1999 Draft made up for a dearth of top-line talent with a frenzy of trade activity among the top picks. Three of the top four and seven of the first 11 selections were traded. Based on the aforementioned poor quality of the draft class, few of the clubs that traded away lottery picks were burned by their wheeling and dealing, save for one: the Atlanta Thrashers, who happened to wind up with the No. 1 pick.
After the draft lottery, the Thrashers were awarded the No. 2 pick, a coveted selection but one shy of the top pick they'd need to nab uber-prospect Patrik Stefan. Fortunately, they found a willing trade partner in Vancouver, whose tireless tweaking left them with two top four picks. In the end, the Thrashers got their man, who was worth all of 59 goals over six underwhelming seasons. The down-trading Canucks had to settle for future Hall of Famer Daniel Sedin.
17 Ryan McDonagh (Montreal Canadiens)
Scott Gomez merits plenty of respect for putting together a decorated 17-year NHL career that included 181 goals and 756 points over 1,079 games played. But Gomez never recaptured the magic of his 84-point 2005-06 season in New Jersey, something the Rangers had realized by the summer of 2009. The Montreal Canadiens, however, hadn't.
The Habs agreed to take on Gomez and a hefty contract that still had five years and $33.5 million on it in a seven-player swap. The former Calder winner scored 12 goals in his first campaign in Montreal and never reached that number again. In return, the Rangers landed a package that included Ryan McDonagh, the club's current captain and No. 1 defenseman.
16 Marcel Dionne (Detroit Red Wings)
Whether you associate the Red Wings with the recent Datsyuk/Zetterberg era, the Yzerman/Fedorov era or the Gordie Howe period, hockey fans of all ages typically view the franchise as a winner. But that hasn't always been the case. The early 1970's in Motown featured a bottom-feeding hockey team with Marcel Dionne and not much else.
In fact, Dionne got so fed up with the Wings' losing ways that he and agent Alan Eagleson strong-armed the club into a trade to Los Angeles in 1975. Given that Dionne had basically agreed to a contract with the Kings while still in Detroit, the club didn't have much trade leverage and wound up giving the future Hall of Famer and six-time 50-goal scorer away for spare parts.
15 Ville Leino (Buffalo Sabres)
July 1st, the traditional opening day of NHL free agency, has long been identified as the day of the most mistakes made by hockey executives. In 2011, one of those erroneous teams was the Buffalo Sabres, who somehow convinced themselves that long-time depth forward Ville Leino was worthy of six years and $27 million.
Leino was coming off something of a breakthrough campaign in Philadelphia, recording 19 goals and 53 points for the Flyers. Still, there wasn't much evidence that the Finnish winger would sustain that pace. He didn't, amassing just 10 goals over the next three seasons, including none in 2013-14. Before being bought out less than three years after signing his deal, Leino was being benched and likening his tenure in Buffalo to a prison stay.
14 Adam Oates (Detroit Red Wings)
Rarely do you hear Adam Oates' name mentioned among the long list of young talent acquisition home runs by the Detroit Red Wings, even though the club brought in the Hall of Fame centre as an un-drafted free agent. That's because unlike Nick Lidston, Sergei Fedorov and Henrik Zetterberg, Oates didn't enjoy his best years in Motown.
Oates was showing signs of the prolific pivot he'd become when he was dealt to St. Louis by a Wings team believing they would be better positioned to win without him. They used him as a trade chip alongside Paul MacLean to land aging vets Bernie Federko and Tony Mckegney. Neither man would last more than a year in Detroit, while Oates was just scratching the surface of a career that would see him net 1,420 career points.
13 Tuuka Rask (Toronto Maple Leafs)
Even by the low standards of a laughingstock Toronto Maple Leafs franchise that remains mired in a 50-year Stanley Cup drought, John Ferguson Jr. was a bad GM. You can count the Jason Blake contract, the Vesa Toskala trade and the Pat Quinn firing among some of his most inept moves. But even then, nothing quite matched the stupidity of his bungling of the club's goaltending situation in 2006.
Though hardly a wellspring for young hockey talent, the Leafs' system did boast an exceptional one-two punch of netminding potential in Tuukka Rask and Justin Pogge in the mid-2000's. Looking to ship one out in exchange for present help, Ferguson opted to keep Pogge (first wrong move) and send Rask to Boston for reigning Calder winner Andrew Raycroft (second wrong move). Raycroft fizzled in Toronto, Pogge barely sniffed the NHL and Rask has shored up the Bruins' net for a decade. Typical Ferguson.
12 Brad Richards (New York Rangers)
Unlike the New York Rangers' previous hefty free agent contracts doled out to the likes of Wade Redden and Bobby Holik, their signing of Brad Richards seemed at least defensible at the time. The Rangers were one of many suitors for the proven No. 1 centre, so they felt the need to go all out with a nine-year, $60 million contract offer to secure Richards' services.
From the get go, Richards' production started to lag upon reaching NYC. His 66 points were his worst in a full season since his second year in the league. Things only got worse in the next two years, expediting the need for a buyout. Through the terms of the costly buyout, the Rangers will continue to pay the former Tampa Bay Lightning and Dallas Stars forward until the 2025-26 season.
11 Theoren Fleury (Chicago Blackhawks)
A beloved superstar on account of his scoring prowess and diminutive size, personal issues that included substance abuse problems were always part of the story for Theo Fleury. While his ability to overcome those problems helped forge his cult hero status, they also contributed to a tenure in Chicago that led to the end of his NHL career.
Upon signing with the Blackhawks for two years and $8.5 million, the seven-time All-Star soon found himself succumbing to addiction once again. Before his first season in Chi-town even started, he was suspended for violating the terms of the league's substance abuse program. When the suspension was lifted, it wasn't long before Fleury was at the centre of a drunken bar brawl and, eventually gave into temptation again.
10 Wade Redden (New York Rangers)
New York Rangers GM Glen Sather might have been one of the last people in hockey to recognize that long-time Ottawa Senators defenseman Wade Redden was on the decline when he reached free agency in 2008. Sather wasted no time in inking the 31-year-old to a six-year, $39 million contract that would pay him big money through to age 37.
In rushing to sign Redden on the first day of free agency, Sather ignored tell-tale signs that included a considerable decline in goals and points year to year and a lack of a competitive offer from the Sens, his team of the previous 11 years. Sure enough, that slippage became all too clear once Redden arrived at MSG, scoring just five goals over two seasons in the Big Apple. He would play two years in the AHL before being bought out in 2013.
9 Hiring John Tortorella (Vancouver Canucks)
Head coaches are not subject to trade in the NHL, but the Vancouver Canucks and New York Rangers had what amounted to a coach swap in the summer of 2013. And it was a lopsided one, at that. John Tortorella had been fired by the Rangers in May and joined the Canucks in June, just four days after Alain Vigneault agreed to become head coach of the Blue Shirts following his own termination from Vancouver the month prior.
Vigneault took the Rangers to the Stanley Cup Finals in his first year behind the bench and has reached the postseason in every year since. Tortorella, meanwhile, failed spectacularly. In his one season as Canucks head coach, the club missed the playoffs for the first time in five years amidst a campaign in which he feuded with fans, media and even beloved goalie Roberto Luongo.
8 Phil Esposito (Chicago Blackhawks)
The frenzy surrounding this summer's Expansion Draft was exciting, but nothing compared to the dawn of the expansion era 50 years ago. The league was doubling in size from six to 12 teams, so the Original Six were poised to lose major talent to the new guys. The fear of losing big names for nothing prompted the Chicago Blackhawks to seek out a taker for Phil Esposito, whom Hawks brass felt lacked toughness and scoring touch.
The lowly Boston Bruins were happy to oblige, sending defensive prospect Gilles Marotte to Chicago in a six-player mega-deal. Esposito immediately proved Blackhawks management wrong, scoring 35 goals and 84 points in his first season in Boston. In over eight years in Boston, Espo would win two Stanley Cups and two Hart trophies while scoring 459 goals in 625 games as part of a Hall of Fame career.
7 David Clarkson (Toronto Maple Leafs)
So much of the discussion about David Clarkson over the past four years has centred around his contract, so it makes sense that little has been said about the player or the circumstances around his signing by the Toronto Maple Leafs in 2013. In Clarkson, the Leafs thought they were inking the missing piece on a team that appeared to be on the rise, a club that lost a Game 7 playoff heartbreaker to the Bruins one year prior.
Clarkson, whose opted to wear 71 as a tribute to Wendel Clark, was a fit for his grit and scoring touch, just not the massive seven-year, $36.75 million deal he signed. A career serviceable centre who somehow lucked into a 30-goal campaign in New Jersey, Clarkson didn't come close to even his modest numbers with the Devils. His contract was so bad that then-GM David Nonis was lauded for managing to unload the deal less than two years after it was signed.
6 Mark Messier (Edmonton Oilers)
Believe it or not, Wayne Gretzky's departure from the Edmonton Oilers did not bring an immediate end to the Oilers' dynasty. Mark Messier stepped up as the franchise star in place of No. 99 and led Edmonton to an unlikely fifth Cup in seven years. When Messier left, however, things were never again the same.
Messier was in the midst of contract squabbles with Oilers boss Glen Sather when he was sent to the Big Apple for a package headlined by Bernie Nichols. The impact was immediate, as Edmonton reached one more Conference Final and then missed the postseason in four consecutive years. In New York, Messier made good on a guarantee to end a 54-year Cup drought in just his third year with the Rangers.
5 Cam Neely (Vancouver Canucks)
Trading a future Hall of Fame winger at the age of 20 is bad enough, but to throw in a top five draft pick seems shockingly inept. The Vancouver Canucks saw little in young prospect Cam Neely, so they packaged him with their No. 3 pick in the 1987 Draft to Boston for Barry Pederson.
While Pederson had a respectable career, the hard-nosed Neely soon became a beloved Boston icon. And that third pick? It became sturdy defenseman Glen Wesley, who actually played twice as many games as Neely. If you follow the trade tree on this deal, it actually trickles all the way down to landing the Bruins the pick they would use to select Milan Lucic, who some view as the modern Neely, in 2006.
4 Jaromir Jagr (Pittsburgh Penguins)
The story of Mario Lemieux's on-ice comeback in 2000 is the stuff of NHL legend. 44 months after retirement due to non-Hodgkins lymphoma, Lemieux returned as a member of the Penguins to score 35 goals in 43 games and even earn a Hart trophy nomination. But did it cost the Pens another all-time great?
The Lemieux comeback put the squeeze on Pittsburgh's payroll and left them unable to re-sign Jaromir Jagr. Instead of recouping a windfall for the Czech scoring superstar, the Pens shipped him to the rival Washington Capitals for the forgettable trio of Kris Beech, Michal Sivek and Ross Lupaschuk. The three men would combine to score 13 goals in Pittsburgh, or 70 less than Jagr potted in Washington.
3 Rick DiPietro (New York Islanders)
Somehow, the Alexei Yashin debacle wasn't Mike Milbury's biggest miss as GM of the Isles. One year prior to the Yashin trade, Milbury had taken the unprecedented step of drafting a goalie with the No. 1 overall pick with the selection of Rick DiPietro. By drafting the Boston University star, not only did he pass on the likes of Marian Gaborik and Dany Heatley, but it prompted the trade of a 21-year-old Roberto Luongo on the same day.
And yet, it still gets worse. Injuries and middling play had held DiPietro to all of 143 starts over his first six pro seasons, the the Isles had evidently seen enough to reward him with a 15-year, $67.5 million contract days before his 26th birthday. The eye-popping investment anticipated a superstar ascension that never came. Instead, DiPietro was waived in 2013 with eight years still remaining on a deal the club will be paying through 2021.
2 Eric Lindros (Philadelphia Flyers)
Even in an era featuring once-in-a-generation draft talents like Connor McDavid and Auston Matthews, it has been some time since we've seen any NHL prospect like Eric Lindros. The rare combination of super-human size and a gifted scoring touch made the Big E the most coveted of draftees. When it became known that Lindros had no desire the join the top pick-holding Nordiques, clubs were ready to pounce.
It was Philadelphia's offer of basically their entire farm system that won them the sweepstakes. Lindros starred for the Flyers, but the Nordiques - or more accurately the Colorado Avalanche - came away with future Hall of Famer Peter Forsberg, who would go on to win a Hart trophy while bringing two Stanley Cups to the Mile High city.
1 Wayne Gretzky (Edmonton Oilers)
Only the most famous of transactions can simply be known as "the Trade" and the dealing of the best player in NHL history fits the bill. Wayne Gretzky was only 27 at the time of the 1988 deal to LA and his Edmonton Oilers certainly knew what they were giving up. But owner Peter Pocklington needed money on account of other failed business ventures, greasing the skids for a move that once seemed impossible.
To no one's surprise, it didn't work out for Edmonton. Some post-trade success only served to showcase the depth of the dynastic club. Soon thereafter, the Oilers endured a fall from relevance that they've only recently recovered from thanks to Connor McDavid's arrival. When Martin Gelinas is the best player you receive in exchange for "the Great One", you've made a bad trade.