Top 5 What-Ifs in Toronto Maple Leafs Team History

The Toronto Maple Leafs season was stopped short due to the pandemic, so there will be a ton of what-ifs if it never returns.

Throughout Toronto Maple Leafs history, and sports in general, every season is filled with what-ifs and what could have been.

Every season, one goal scored or allowed can be the difference between pain and pleasure. It can also have a ripple effect on the rest of history that torments fans for years to come.

With over 100 years of history, the Toronto Maple Leafs are filled with what-ifs. For this season alone, there are a number of what-ifs that could have happened if the season was never shut down.

For example, would Auston Matthews have scored 50 goals? Should the Leafs have traded Tyson Barrie? What if Andreas Johnsson and Morgan Rielly didn’t get injured, or what if the Leafs traded for a back-up goaltender at the beginning of the season?

The questions will always remain unanswered but it’s still interesting to see what could have happened if certain things went differently.

Here are the top-five what-ifs in Toronto Maple Leafs history:

#5. What if the Leafs never traded Tuukka Rask?

In 2005, the Leafs used their first round draft pick on a goaltender named Tuukka Rask from Finland.

Unfortunately the Toronto Maple Leafs didn’t know the old hockey homage in 2006: “When in doubt, stick with a finnish goalie.”

So what if the Toronto Maple Leafs kept Rask instead of trading for Andrew Raycroft?

It took until the 2009-10 season for Rask to become a steady back-up goaltender in the NHL, and Boston had the luxury of having Tim Thomas in front of him to learn. Rask slowly transitioned into the league as a starter and eventually became a Vezina Trophy goaltender but it took nine years after his draft year to do so.

As much as we could have hoped that Rask would have had the same results in Toronto, the Leafs unfortunately did not have another quality goaltender that he could have been groomed behind.

If Rask was a Leafs goaltender, it’s possible that he could have been called up too early and not developed the same way he did in Boston, so as much as this what-if angers Leaf fans daily, Rask most likely wouldn’t have been the goalie he is today.

#4. What if the Leafs won Game 7 Against Boston in the 2013 NHL Playoffs?

It’s the game that every Leaf fan wants to forget. Everyone remembers where they were when they watched their favorite team give up a 4-1 lead in the third period on the road in Boston.

It’s arguably the worst loss in franchise history and the team has still yet to win a first round playoff match-up since 2004. But in this world of revisiting history, what would have happened if the Toronto Maple Leafs won that playoff series and continued on their Stanley Cup run.

In the second round, the Leafs would have had home-ice advantage against the New York Rangers. Battling against Henrik Lundqvist would have been a tough test but with home-ice, there’s no reason why they could have stolen that series.

From there, the Leafs very well could have found themselves in the Eastern Conference Finals against Pittsburgh. The team most likely would have ran out of gas by then, as the Sidney Crosby led Penguins would have been too much of a match for Toronto, however you never know.

Overall, if the Leafs won this series it would have been the worst thing to ever happen to them. They may have gave Randy Carlyle a longer lifespan and the team’s rebuild may never have happened so quickly. Thank goodness they never won that game.

#3. What if the Leafs Won the 2015 NHL Draft Lottery?

With a 9.5% chance at winning the 2015 NHL Draft Lottery, the Toronto Maple Leafs had the fourth best odds at winning.

Unfortunately for Leafs fans, the Edmonton Oilers were victorious in this lottery and had the opportunity to draft Connor McDavid.

Instead of McDavid, the Leafs drafted Mitch Marner with the fourth overall pick that year. Don’t get me wrong, Marner is a generational talent but he’s no McDavid.

McDavid is the best player in the NHL and will be for the next decade. So what would have happened if the Leafs won the lottery?

With McDavid on the Leafs, the 2015-16 rebuild actually may still have happened. When McDavid joined Edmonton, they were still the second worst team in the NHL a year later. The Leafs roster in 2015-16 with McDavid was still so terrible, that there’s a real chance the team would have had a top-five pick again.

Instead of having Nylander, Matthews and Marner, the Leafs core would probably have looked something like this: Nylander, McDavid and Matthew Tkachuk or Patrick Laine.

Although the Leafs current core is great, that core is better. Matthews is arguably the greatest goal-scorer to ever play for the Leafs, but McDavid has potential of being one of the best 10 player to ever play in the NHL, so winning the lottery would have given the Leafs a better chance at winning a Stanley Cup.

#2. What if the Leafs never traded for Phil Kessel?

In 2009, Brian Burke traded two first round picks and a second round pick for Kessel. At the time, the move seemed justified as the opportunity to bring in a prolific goal scorer was something the Leafs desperately needed.

However, two of those draft picks turned into Tyler Seguin and Dougie Hamilton, and although Kessel had four 30-goal seasons in Toronto, the team never had playoff success and Kessel was a punching bag for Toronto media.

So what would have happened if Kessel never became a Leaf?

While, the team would have had two first round draft picks that could have shaped the franchise. It’s possible that the Tyler Seguin experiment would have been too much in Toronto. Seguin was known for his party lifestyle and getting drafted to his hometown team could have been too much to handle for the young player.

The Bruins saw Seguin’s off-ice routines as an issue and traded him only three years into his career, despite his numbers being great.

And although Boston drafted a good defenseman in Dougie Hamilton, if the Leafs kept that pick, it’s possible they would have screwed it up. For example, in that same draft the Leafs drafted Tyler Biggs and Stuart Percy when players like Boone Jenner and Rickard Rakell were available.

So although the Leafs traded away a lot of assets for a one-trick pony in Kessel, it’s likely management wouldn’t have drafted well with the picks they had, so at least fans had the pleasure of watching Kessel for a few years.