25 Biggest "What Ifs" In Hockey... And How They Could've Been Different

For every great sports moment there is, and for every great player there is, we always ask ourselves how things could have wound up being different. There is always a time where a different decision (by a coach, general manager, owner, etc.) could have changed the landscape of the NHL. There are times where a non-officiating mistake could have made history incredibly different.

And there are times where players made a bad mistake on the ice, something that hurt them throughout the rest of their careers. When it comes to drafting, player injuries, official mistakes, decisions made by a team's management or anything else, we always ask ourselves how history could have been different. There are some times where the "what if" game leaves us with obvious answers. There are other times when we purely speculate what other things could have happened if a moment turned out differently.

Here are the 25 biggest "what ifs" in hockey history.

25 Jaromir Jagr Never Left the NHL


Jagr was one of the NHL's longest-tenured superstars. He won back-to-back Stanley Cups with the Pittsburgh Penguins in 1991 and 1992. He won five Art Ross Trophies as the league's top scorer as well as the Hart Trophy in 1999. Nobody dominated the '90s and 2000s as consistently as he did.

After three and a half seasons with the New York Rangers, Jagr left the NHL to play three seasons for Avangard Omsk of the KHL. Though the Rangers qualified for the playoffs in 2009 and 2011, Jagr's presence was clearly missed. He returned in the 2011-12 season, and has maintained his high level of play into his 40s.

What Would Have Happened: Jagr would obviously remain a top player on the Rangers. If he was on their 2009 squad, they would have been one of the Eastern Conference's top teams and could have reached the Stanley Cup.

24 Ottawa Senators Choose Zdeno Chara over Wade Redden


After finishing first in the Eastern Conference before an early playoff exit in the 2005-06 season, the Ottawa Senators were left with a difficult decision. They could only afford to keep pending free agent Zdeno Chara or Wade Redden. The team led Chara walk and join the Boston Bruins, where he won a Stanley Cup with them in 2011. Redden spent the next two years in Ottawa before leaving for salary cap purposes.

Redden helped Ottawa reach the 2007 Stanley Cup Final, but they were dominated and ousted in five games by the Anaheim Ducks.

23 Dwayne Roloson Played the Entire 2006 Stanley Cup Final


Before the Edmonton Oilers traded for Dwayne Roloson at the 2006 trade deadline, they were a playoff bubble team. With his addition, they took the Western Conference's final playoff spot and rode the hot glove of Roloson in the playoffs. They took out the President's Trophy-winning Detroit Red Wings, Hart Trophy-winning Joe Thornton and his San Jose Sharks, and eventually the Anaheim Ducks.

They faced the Carolina Hurricanes in the Stanley Cup Final. Roloson, who was unreal throughout the postseason, sprained his MCL in Game 1. Carolina rallied to steal the first game and saw a 3-1 series lead. They wound up winning the cup in seven games.

22 Dan Cloutier Keeps it Simple


The Vancouver Canucks barely qualified for the playoffs in the 2002 season. They had to face off against the President's Trophy-winning Detroit Red Wings, who appeared destined for their third cup in six years.

Vancouver shocked Detroit, winning the first two games on the road with a chance to go up 3-0 at home. With the game tied 1-1 in the final minute of the second period in Game 3, Dan Cloutier tried to glove Nicklas Lidstrom's slap shot from centre ice. The only problem is that the puck didn't go into his mit, but rather the back of the net.

Detroit would hold on to win Game 3, before winning Games 4-6 and eliminating the Canucks. The comeback propelled them to a Stanley Cup victory.

21 Peter Forsberg Stayed Healthy

Ron Chenoy-USA TODAY Sports

Though most of us remember Patrick Roy and Joe Sakic as the two key cogs on the Avalanche's Stanley Cup championship squads in 1996 and 2001, Forsberg was just as important to Colorado's success.

His stats were remarkable: 249 goals and 885 points in 708 games. That's right, in 14 NHL regular seasons, Forsberg played 708 out of a possible 1,114 games. That's excluding the 2001-02 season, where he only played in the playoffs. He won the Hart Trophy and Art Ross Trophy in 2003, and was a three-time NHL First Team-All Star.

20 Boston Bruins Have Five Skaters (1979 Playoffs)


Though most of us remember Don Cherry as the witty, eccentric and entertaining host of Coach's Corner on Hockey Night in Canada, the other half of his legacy is a coaching mistake that overshadowed his career as a bench boss.

In the 1978-79 Semifinals, the Bruins led the Montreal Canadiens 4-3 in Game 7 at the Montreal Forum. With 2:34 to go, the Bruins were called for too many men, a penalty that was rarely called back in those days. The shot of Cherry's frustration has become iconic as it plays in the intro of Coach's Corner.

Guy Lafleur would score the game-tying goal late, forcing overtime. The Canadiens would then win in overtime before defeating the New York Rangers for the Stanley Cup. It would be 32 years before Boston won the Cup again.

19 Todd Bertuzzi Leaves Steve Moore Alone


In one of the ugliest and worst moments in NHL history that benefited absolutely no one, Todd Bertuzzi tarnished a remarkable career while ending another.

The Vancouver Canucks and Colorado Avalanche faced off in a regular season game on March 8th, 2004. While the Avs were blowing out Vancouver, Todd Bertuzzi was looking for comeuppance from an earlier incident. Earlier that season, Avalanche tough guy Steve Moore delivered an ugly head shot to Canucks' captain Markus Naslund.

Bertuzzi followed him and tried instigating a fight during that game, but Moore refused. Later on, Bertuzzi sucker punched him in the neck, fell on him, and started a dog pile on top of Moore.

The Canucks lost a top scorer for the season, as Bertuzzi was suspended for the remainder of 2003-04. Moore's injuries were far too severe and he couldn't play again. On his way to a fifth-straight 20-goal season, Bertuzzi's 2005-06 season was his last in Vancouver. He would be traded to the Florida Panthers in the Roberto Luongo blockbuster, but he never reached 20 goals again.

18 Sedin Twins Were Split Up

Anne-Marie Sorvin-USA TODAY Sports

Former Vancouver Canucks General Manager Brian Burke pulled off one of the biggest and most impressive trades in NHL history during the 1999 NHL Entry Draft. So here was the deal:

Henrik and Daniel Sedin were identical twins who starred in Sweden. Both of them wanted to play together. The only problem was they were both hyped to be elite prospects, so it would have been next-to-impossible for most GMs to make something work.

The Canucks had the second pick, but traded up to land the third as well. Daniel went after the top pick, Patrik Stefan. His brother Henrik was right behind him, and the two twins were both united as one in Vancouver. Though the Canucks haven't won a Stanley Cup yet, they were a top dog in the NHL for years. Each brother has Olympic Gold and an Art Ross, while Henrik also won a Hart Trophy.

What Would Have Happened: Burke worked non-stop to convince the Atlanta Thrashers to take Patrik Stefan (Tampa Bay originally held the top pick.) So what would have happened? The Lightning would have taken Daniel and the Canucks would have Henrik. The Canucks would remain an NHL-worst for years, while Daniel does enough in Tampa to be part of their 2004 Stanley Cup squad.

17 Steve Smith Doesn't Score On His Own Net


Though the Edmonton Oilers saw more than their fair share of success in the '80s (and 1990) with five Stanley Cups, you always want more. There's just no way any team in pro sports would settle for less if they could have it their way.

During the 1986 Smythe Division Final, the Oilers faced their arch-rivals, the Calgary Flames. With just over five minutes remaining in the third of Game 7 (knotted at two apiece,) Smith went behind the net and put the off of his goalie and in the net.

Of course, the Flames would hang on and go all the way to the Final, before losing to the Montreal Canadiens. The Oilers chance at a three-peat was denied.

16 Eric Lindros Stayed Healthy

Eric Hartline-USA TODAY Sports

Eric Lindros in 1991 was a modern Connor McDavid. He was a once-in-a-generation prospect that you could not miss. The Quebec Nordiques were royally screwed when they drafted him before he demanded an eventual trade to Philadelphia.

This Lindros guy wasn't a draft bust by any means. A seven-time All-Star and Hart Trophy winner, Lindros made the Flyers one of the NHL's most dominant squads during the '90s and early 2000s. He was a four-time 40-goal scorer and helped them reach the Stanley Cup Final in 1997 before losing to the Detroit Red Wings.

372 goals and 865 points in 760 games are remarkable stats, but they could have been greater. He never played a full NHL season and played 70-plus games only four times.

15 Calgary Flames Get The Call In 2004


The 2004 Calgary Flames were one of the biggest Cinderella stories ever. After taking down the Vancouver Canucks, powerhouse Detroit Red Wings and San Jose Sharks, they appeared destined to steal the Stanley Cup from the Lightning.

With the Flames up 3-2 in the series, they had a chance to clinch the Cup on home ice in Game 6. With the match knotted at two goals apiece, Martin Gelinas appeared to have scored a go-ahead goal with 6:57 left in the final frame, but it wasn't called a goal. The officials never reviewed it, however. Game 6 went into overtime, where the Lightning won of course. The Flames would lose Game 7, and were unfairly losers of an intense seven-game series.

14 Nathan LaFayette: An Inch to the Left


For those of you who aren't familiar with the name of Nathan LaFayette, that's because he wasn't a superstar by any means. He was a hard-working bottom-six forward on the 1993-94 Vancouver Canucks, who shocked everyone by making it all the way to the Stanley Cup Final.

They had the challenge of facing the President's Trophy-winning New York Rangers. The Canucks stole Game 1, but lost three in a row. However, the team rallied to steal Games 5 and 6, setting the stage for an epic Game 7.

Mike Richter stood on his head all game and the Rangers led 3-2 late. With five minutes to go, the puck came right in front to LaFayette, who was all alone in front. However, he hit the goal post and the Canucks failed to tie it up.

13 Ottawa Senators Select Chris Pronger Over Alexandre Daigle


The Senators thought they had themselves a new franchise superstar when they took Alexandre Daigle with the first pick in the 1993 NHL Draft. Chris Pronger went right after him, going to the Hartford Whalers.

Daigle had 129 goals and 327 points in 616 games. He spent just four years in Ottawa and never became the superstar they had hoped for. As for Pronger? He'd win a Hart, a Norris, two Olympic Gold Medals, a Stanley Cup and made it to six All-Star games.

Ottawa would once again be reminded about how they made the wrong choice when Pronger's Anaheim Ducks shut down the Sens' heavy offense in the 2007 Stanley Cup Final, dispatching them in five games.

12 Bobby Orr Didn't Need To Retire Early


After Gordie Howe and before Wayne Gretzky, there was number four, Bobby Orr. The most dominant defenceman to ever live won eight Norris Trophies, two Art Ross Trophies, three Harts, two Conn Smythes and, of course, two Stanley Cups. Orr managed to post 270 goals and 915 points in just 657 games.

Orr also hit the 100-point plateau a remarkable five times in his career. Sadly, he had to go through over a dozen knee surgeries in his career to the point where he couldn't play any more. Orr was forced to retire at the young age of 30 and fans were left to wonder what more he could have done if his knee stayed healthy.

11 Quebec Nordiques Don't Take Eric Lindros In 1991


The Nordiques were the lucky winners of the Eric Lindros sweepstakes, taking the once-in-a-generation prospect first-overall. He refused to play for them and was traded to the Flyers in a blockbuster deal a year later.

Now, the Nordiques did get some nice pieces in return, including prospect Peter Forsberg. However, Lindros said ahead of time he wouldn't join them. Scott Niedermayer, Markus Naslund, Alexei Kovalev and Brian Rolston were a few of the big names the Nordiques cold have taken instead.

Taking Lindros and subsequently trading him did nothing for the franchise, as they were forced to move to Colorado in 1995-96.

10 Canadiens Don't Acquire Guy Lafleur


The Montreal Canadiens have had many legends over the years: Howie Morenz, Maurice Richard, his younger brother Henri, Jacques Lemaire, Doug Harvey, Jacques Plante, Patrick Roy, Jean Beliveau, Steve Shutt, the list goes on.

And then there's "The Flower," Guy Lafleur. The California Golden Seals owned the first pick in the 1971 NHL Draft, but Habs GM Sam Pollock wanted to get Lafleur badly. He used his genius to acquire it and the Canadiens had their new franchise superstar.

Lafleur went on to become the Habs all-time scoring leader (1,246 points,) while winning three scoring titles and Two Harts. He also led them to five Stanley Cup championships, cementing his legacy as one of the NHL's all-time greats.

What Would Have Happened: The Golden Seals moved to Cleveland before going to Minnesota. They're now the Dallas Stars franchise. Having a superstar like Lafleur could have kept the Golden Seals in Oakland permanently, for all we know.

9 Marty McSorley Uses a Legal Stick


The 1993 Stanley Cup Final was one of the most intriguing to some. The league's most historic franchise, the Montreal Canadiens, looked to add another title with superstar goalie Patrick Roy carrying the load. Meanwhile, Wayne Gretzky's Los Angeles Kings got to the Final in controversial fashion (more on that later).

Los Angeles stole Game 1 in the Montreal Forum and appeared poised to go up 2-0 heading back to the Golden State. However, late in the third period, the Habs asked the officials to check Marty McSorley's stick for an illegal curve. Sure enough, it was beyond the legal limit and he was penalized.

Eric Desjardins tied it up late on the powerplay before winning it in overtime. The Canadiens would take Games 3, 4 and 5 and capture their 24th championship. The Kings never recovered from that, and it would be 19 years before they won a Stanley Cup.

8 Howie Morenz Doesn't Break His Leg


Howie Morenz is widely described as hockey's first true superstar, the guy who was heads-and-shoulders above everyone else on the ice and the player that fans paid specifically to watch.

The Stratford Streak led the league in scoring twice while winning three Hart Trophies. He led the Habs to three Stanley Cup championships, paving the way for hockey's greatest franchise to find more talents that would carry them like Maurice Richard, Doug Harvey and Jean Beliveau.

Sadly, during a home game against the Chicago Blackhawks, Morenz had a horrific crash in the boards which broke his leg. Being told he wouldn't be able to play hockey again, Morenz grew deeply depressed. A couple months later while in the hospital, Morenz passed away, which doctors attributed to his injuries.

7 Wayne Gretzky Doesn't Get Away With It


The poor Toronto Maple Leafs fans haven't been able to catch a break since they last won the Stanley Cup in 1967. Forget the fact they haven't won a conference championship in nearly 50 years or losing Game 7 of the 2013 Playoffs to the Boston Bruins in terrible fashion.

Nothing will beat their devastating loss to the Los Angeles Kings in the Clarence Campbell Conference Finals. With the Leafs leading the series 3-2, they appeared poised to reach the final. All they needed was one more goal in Game 6 at Los Angeles and they'd be in the Cup Final for the first time in 26 years.

In overtime, Wayne Gretzky high-sticked Doug Gilmour and cut his chin. In those days, that was a five-minute penalty and game misconduct. However, the officials infamously missed the call. Of course, Gretzky stayed in the game and scored the game-winner. He'd register a hat trick in Game 7, as the Kings defeated Toronto to reach the Final. The Habs would then take them down in five games.

What Would Have Happened: The Leafs and Habs will never be put into separate conferences. Seeing a historic rival one more time in the Final would have been purely epic.

6 Brett Hull's Golden Goal Doesn't Count


The 1999 Stanley Cup Final featured the powerhouse Dallas Stars, led by Mike Modano, Ed Belfour, Joe Nieuwendyk, Brett Hull and Jamie Langenbrunner representing the Western Conference. Meanwhile, the Buffalo Sabres were strictly an underdog story led by perennial Vezina winner Dominik Hasek.

This series was one of the more entertaining bouts, as two future Hall of Fame netminders duked it out. Sadly, one of the most memorable Finals just had to end in controversial fashion. It just had to.

Brett Hull would score the Cup-winning goal in Game 6 in overtime. However, rules at that time stated that players could not score with their foot(s) in the crease. The officials never witnessed or reviewed it and the Stars took the Cup away from the Sabres in extremely controversial fashion.

What Would Have Happened: With the Dominator standing on his head, the Sabres would win Game 6 in overtime. Fuelled by the emotional home win, Buffalo and Hasek save their best for last, taking down the Stars and winning the Cup.

5 2004-05 Lockout is Avoided


There's no way in knowing how exactly everything would have happened if this lockout didn't take place. The Pittsburgh Penguins may not have even won the Sidney Crosby sweepstakes. Maybe eventual Stanley Cup Champions like Carolina, Anaheim and Detroit don't sustain success from the post-lockout.

But we'll try to give this a go. Obviously, it was a huge loss when Gary Bettman had to shut down the entire season. It was a brand new era for hockey: They introduced new rules (getting rid of the two-line pass, delay of games for puck over glass and the trapezoid), while introducing the salary cap.

The NHL has since seen all-time high in revenues. Sidney Crosby and Alex Ovechkin single-handedly saved two franchises that were making no money and couldn't put fans in seats.

But here's what matters most. Who would have won the Stanley Cup in the 2004-05 season?

4 Patrick Roy Stays with Montreal


Patrick Roy was the heart and soul of the Canadiens for nearly a full decade. He captured the love of Montreal by winning the 1986 Stanley Cup as a rookie. He propelled them to greatness, also leading them to another championship in 1993.

In Montreal, he won two Conn Smythes, three Vezinas and made it to six All-Star games. 289 of his career 551 wins came with the Habs. This team was definitely always on the brink of greatness, thanks to their star netminder. But then came December 2nd, 1995. The Canadiens hosted the Red Wings and lost 11-1. Coach Mario Tremblay made a costly decision to keep Roy in for nine of the goals surrendered.

With the fans booing heavily and Roy finally being pulled, he told the Habs he had just played his last game with the team. And so, one of the most lopsided trades ever took place. You know the rest: Roy becomes the backbone of Colorado's dominance in the '90s and early 2000s, leading them to the Cup in 1996 and 2001.

The Habs, meanwhile, are still searching for their first trip back to the Final since winning it all in 1993. A costly decision by Tremblay prompted a trade that shifted the momentum of Montreal's success. They spent years trying to rebuild a talented squad.

3 Mario Lemieux Stays Healthy

Charles LeClaire-USA TODAY Sports

A healthy Mario Lemieux would have meant a debate as to if he or Wayne Gretzky was the best NHL player to ever live. Though Super Mario made a decent case for himself, we could have seen a whole lot more greatness.

Sadly, Lemieux was diagnosed with Hodgkin's Lymphoma and had to miss 24 games, though he wound up winning the scoring title and leading the Pens to the President's Trophy. Injuries also forced him to retire and miss 1997-98, 1998-99 and 1999-2000. When he returned in 2000-01, he managed an incredible 35 goals and 76 points.

Lemieux managed 690 goals and 1,723 points in just 915 games. He never played a full season and played 70-plus games just six times. He also had four seasons where he played 26 games or less.

Still, he did lead the Pens to a pair of Stanley Cup victories while winning three Hart Trophies, two Conn Smythes and five scoring titles. Of course, he also saved the team from possible relocation in 2005-06, taking over as co-owner while leading them to championships in 2009 and 2016.

2 Edmonton Oilers Don't Trade Wayne Gretzky


There was no reason for the Oilers to trade The Great One that had led them to four Stanley Cups, but of course owner Peter Pocklington did so. He had to get cash back while in some financial difficulties. Little did he know that The Trade would become one of the darkest moments in the team's history.

Everyone knows what Gretzky did in Edmonton. That's where he experienced most of his career. There would not have been a dynasty without him. Yes, the Oilers did win the Cup again in 1990 when he was long gone to Los Angeles, but they could have done even more damage in the league with him.

They also got very little in return, unless $15 million to help Pocklington's businesses counts to the fans.

1 WHA and NHL Don't Merge


The NHL was easily the most attractive hockey league in the world and they did feature most of the top stars. But the WHA wasn't all that far behind. After all, Wayne Gretzky had started his career there.

Both leagues had plenty of fierce competition, going into many lawsuits over the years. The WHA lasted seven years, but eventually came to an agreement with the NHL to merge in 1979. That meant that the Edmonton Oilers, Quebec Nordiques, Winnipeg Jets and New England Whalers (later Hartford) would join the NHL.

As such, the NHL became the undisputed top hockey league in the world. Talents like Peter Stastny, Gretzky, Andre Lacroix and others made the jump. The NHL landscape would forever change.

What Would Have Happened: Eventually, the merger would have had to take place. It was inevitable. But if it waited itself out longer, the Oilers dynasty would not have happened. The Nordiques could have possibly avoided moving to Colorado... The list goes on. So many star talents would not have been witnessed in the NHL if the WHA didn't join forces. Let's just be grateful the merger happened.

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25 Biggest "What Ifs" In Hockey... And How They Could've Been Different