As the Canadian Stanley Cup drought reaches 30 years, a great deal of focus continues to ride on how close each Canadian NHL franchise may or may not be to winning a Stanley Cup. Though the seven Canadian teams find themselves in various stages in pursuit of this ultimate goal, two teams have distinguished themselves above the pack. Although some hope exists with the likes of the Calgary Flames, and to some extent the Ottawa Senators, the Edmonton Oilers and Toronto Maple Leafs are clearly in a class of their own.
Due to the nature of their full rebuilds and their convergent timelines in the act of such, comparisons between the two teams has been even more natural. From rabid fan bases to superstar players, both the Oilers and Leafs do bear their fair share of similarities, but their successes, or lack thereof, have been compared and contrasted throughout their respective rises to prominence.
In going over a brief history of their journeys to this point, let’s analyse the steps each team has made and what steps still need to be taken. Ultimately, which team is more likely to end Canada’s Stanley Cup drought, the Oilers or the Leafs?
Oilers’ history since drafting McDavid
Connor McDavid’s rookie season in 2015–16 was cut short with injury, but the hype of his NHL arrival was clearly justified. Although the Oilers missed the playoffs that year, they were able to author a run to the second round in the 2016–17 playoffs. Leon Draisaitl had the first of his outstanding playoff performances, with 16 points in 13 games. The Oilers future appeared bright after finishing eighth in the NHL and showing strong in the playoffs.
What happened next would not go according to plan, as the Oilers failed to qualify for the playoffs in both 2017–18 and 2018–19. This was a dark time for the Oilers, with national media pedalling speculation that McDavid and Draisaitl would not be keen to remain with the team long term due to the awful results. The Oilers, understandably, made a change at GM, transitioning from Peter Chiarelli to Ken Holland.
In Holland’s first season the Oilers were on pace to make the playoffs,returning to a semblance of respectability, though still a flawed team outside of their two superstars. Though the Oilers were eliminated by the Chicago Blackhawks in the play-in round of the strange COVID-19 bubble playoffs in the summer of 2020, the team was at least headed in the right direction.
Leaf’s history within the same timespan
Meanwhile in Toronto, the Leafs were still a bottom feeding team during McDavid’s rookie season. Earning the first overall draft choice, so to speak, and selecting Auston Matthews would represent the end of an hapless era. With Matthews, Mitch Marner, and William Nylander debuting in 2016–17, the Leafs would make an instantaneous rise to relevance, qualifying for the playoffs.
Though the Leafs enjoyed more consistent regular season success than the Oilers over this period, they were unable to equal the Oilers’ playoff success, failing to win a playoff round. Still, there was some optimism, as the Leafs remained on a path to perennial contention, improving their regular season results.
The Leafs would end their 19–20 season in similar fashion to the Oilers, losing a play-in round to a lower seed, as the Leafs fell short against the Columbus Blue Jackets. Though both play-in series losses were disappointing, the strange nature of the bubble playoffs, and the world at large, might have eased some of that disappointment.
After the pandemic bubble playoffs
During the 2020–21 season the NHL essentially split into four leagues, with newly formed divisions facing off exclusively against their new divisional rivals. The Oilers and Leafs found themselves as favourites in the North Division, effectively the Canadian Division. The Leafs continued their strong regular season play, winning the top seed comfortably, while the Oilers followed behind finishing second.
Despite both teams delivering on preseason prognostications, the Oilers and Leafs both suffered embarrassing first round defeats to the Winnipeg Jets and Montreal Canadiens respectively. The Oilers were swept by the Jets, while the Leafs coughed up a 3–1 series lead.
As the world started to return to normal during the 2021–22 season the Oilers got off to a worrisome start to the season. After a strong opening month the Oilers spiralled into a December and January that bordered on winless. With the mood around the team grim, tempers flared, eventually leading to then Coach Dave Tippett being fired.
With new Coach Jay Woodcroft in the fold, the Oilers would finally start delivering a performance worthy of pride. The Oilers would improve their control of play, attention to detail, and ultimately their record, moving from outside of a playoff spot into one of the league’s best teams in the back half of the regular season. These results continued in the playoffs as the Oilers would make it to the third round before losing to the eventual Cup champion Colorado Avalanche.
Meanwhile, the Leafs had a much more stable season, staying true to their reputation as a strong regular season team that could not find a way to win a playoff round. Though the Oilers had some ups and downs, they had at least shown some proof of concept by winning a few playoff rounds during the McDavid era.
The current season ended too soon for both teams
Both the Oilers and the Leafs had similar experiences in 2022–23, finishing second in their respective divisions, finishing sixth and fourth respectively in the overall standings. Both teams have continued to improve their regular season performances, and made improvements to their lineup at the trade deadline. Both teams would advance to the second round before being eliminated, but it was at this point that their paths diverged.
The Oilers defeated the Los Angeles Kings in the first round for the second straight season, while the Leafs finally won a playoff round by defeating the Tampa Bay Lightning. It might be understandable that the Leafs and their fans celebrated their first round victory more than the Oilers did, given it was their first series win in the salary cap era, but the difference in the mood of the Oilers was noticeably more muted. The Oilers are much more experienced with playoff success, and accustomed to the fact that each round becomes more difficult.
Though both teams lost in the second round, the moods were different during exit interviews as well. The Oilers were steadfast, devastated, and trying to take accountability, clearly evidenced by Draisaitl’s self evaluation despite another amazing individual playoff performance. Meanwhile, despite falling behind 3–0 in their series against the Florida Panthers, the Leafs focused on the positives of their performance, a belief in their process, chances, and play away from the puck despite a lack of production and results.
The changing tides
While questions surrounded both team’s GMs were front and centre, Oilers GM Holland was steadfast on returning to work, echoed by Coach Woodcroft citing that all in the organisation would be using the disappointment as “motivational fuel” heading into the offseason. The Oilers maintained a clear vision on where they could improve and how they could do so.
Meanwhile, the Leafs devolved into something of a soap opera, a process that is still ongoing. Following a detailed recounting of the week after their postseason loss, Leafs President Brendan Shanahan publicly aired grievances with now former GM Kyle Dubas and the contract negotiations between the two. Though at face value Shanahan’s detailing of the process of moving on from Dubas paints a picture favouring the Leafs, details are continuing to emerge that tell us that there is more to the story.
Reports that Dubas was, on several occasions, blocked from making moves by Shanahan or Leafs ownership have begun to emerge. In less than a week an appraisal of the situation has gone from Dubas being offered a contract extension, to Dubas falling victim to overplaying his hand in contract negotiations, now to the inherent autonomy of the Leafs GM position being questioned.
With Matthews eligible for a contract extension, a no trade clause for Marner kicking in July 1, rumours that players on the Leafs roster are unhappy with Dubas’ departure, and a large portion of the roster unsigned, the need for a clear vision in Toronto is both critical and absent.
The looming offseason
Though the situation in Toronto seems dire, clouded, and contentious, change can be the jumping off point for improvement as well. Perhaps the hubris and compensation that defined the Dubas era in Toronto will come to an end. There remains some truths to the Leafs circumstances, a strong roster and an uncertain future. Despite their consistent regular season prowess, the Leafs will have a lot of soul searching to do before the opportunity to prove themselves comes with the start of next season.
The Oilers, meanwhile, will have to prove themselves once more as well. The difference here is that the Oilers do so with a clarity of concept and purpose. The Oilers have continued to improve their depth behind McDavid and Draisaitl, as well as their defensive capability as a team. In his end of season availability, new Oilers defenceman Mattias Ekholm outlined the need to complete their defensive transformation, stating that the team would need to continue to embrace their defensive will alongside their improving defensive skill to reach their ultimate goal.
On the basis of clarity alone the Oilers are the team that is closer to a Stanley Cup. This gap continues to widen when we consider the historical results of the Oilers and Leafs respective superstar players in the playoffs. This gap grows further still when we consider the potential internal development of each franchise, as the Oilers have a group of young players that are closer to making a huge difference to the team’s play.
Evan Bouchard is coming into his own as a star defenceman, while Philip Broberg looks to be well underway to an increased lineup spot as soon as next season. Even if we consider the situations up front and in net a wash, with Stuart Skinner and Joseph Woll looking to assert themselves further, and both teams having a pair of young forwards who could fit into their top nine in Dylan Holloway, Raphael Lavoie, Matthew Knies, and Nick Robertson, the Leafs don’t have any equivalent players to Bouchard and Broberg.
As we have seen, the world of the NHL is a volatile one, where things can swing quickly one way or another. Although there is a long offseason of change for both teams ahead, it is almost impossible to suggest that the Leafs are closer to a Cup than the Oilers with any degree of validity. From the standpoint of organisational vision, past performance, and projected growth, the Oilers have a clear edge as Canada’s best Cup hope.
Photo by Curtis Comeau/Icon Sportswire
