After years of mismanagement and ineptitude, the Edmonton Oilers and Toronto Maple Leafs both turned a corner in 2016-17, due in large part to their respective young superstars, Connor McDavid and Auston Matthews.

McDavid, the first overall pick in 2015, lived up to the expectations of being a generational talent along the lines of Sidney Crosby. After a successful (but injury-shortened) rookie season, the 20-year-old was named team captain last fall, led the league with 100 points (30 goals, 70 assists), helped the Oilers to their first playoff series victory since 2006 and won the Hart Trophy.

Matthews took Toronto by storm after being selected with the top pick in 2016. The Scottsdale, AZ native scored four goals in his NHL debut, set Maple Leafs rookie records for goals (40) and points (69), helped Toronto to return to the post-season and won the Calder Trophy. The 19-year-old also handled the media spotlight in Toronto like a veteran while being groomed for a leadership role as a team captain.

The two organizations have not won a championship in a combined 77 years, but likely will be battling for the title of “best team in Canada” for the foreseeable future. With their franchise centerpieces in place, the key to who will win the Stanley Cup first will be who can best surround McDavid and Matthews with the best supporting cast.

In spite of being in only year three of their rebuild, the Maple Leafs appear to be better set up than the Oilers to achieve that long-term success.

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Edmonton’s return to respectability has been delayed by squandering the only fringe benefit of finishing out of the playoffs. Not only did they trade three top-10 picks, including a pair of first-overalls (Magnus Paajarvi, Taylor Hall and Nail Yakupov), the Oilers have not been able to add a significant contributor outside of the first round this decade.

After charting a similar lack of success for years, Toronto reorganized their scouting staff and talent evaluation under team president Brendan Shanahan and Assistant GM Mark Hunter.

From 2014 – 2016, the Leafs selected William Nylander, Mitch Marner and Matthews in the top 10, while also adding key prospects Travis Dermott, Carl Grundstrom and Jeremy Bracco in later rounds, who all appear to be NHL-bound in the near future.

Both clubs hired Stanley Cup-winning GM’s in 2015. In Edmonton, Peter Chiarelli inherited a club with a core group of Hall, Ryan Nugent-Hopkins and Jordan Eberle locked up on long-term deals.

Chiarelli struck pay dirt in acquiring goaltender Cam Talbot from the Rangers, but his moves to address the club’s blueline and cap management have been questionable.

The Oilers dealt a 2015 1st and 2nd round pick to the Islanders for Griffin Reinhart, gave Justin Schultz away to Pittsburgh for a third round pick, swapped the high-scoring Hall to New Jersey for the defensive-minded Adam Larsson and signed veterans Andrej Sekera and Kris Russell to pricey contract extensions.

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After moving Hall to the Devils, the Oilers added veteran Milan Lucic on a seven-year, $42 Million extension last July. The Stanley Cup winner scored 23 goals in his first season with Edmonton, but the big winger had trouble keeping up with the pace of playing with the speedy McDavid.

The Eberle-Ryan Strome deal in late June cleared a large cap hit off the Oilers payroll, but with McDavid’s eight-year, $100 Million contract extension (which goes into effect after next season) Edmonton has $52.2 Million allocated to only 12 players next season, and that does not include a new deal for RFA Leon Draisaitl.

If the Oilers hope to get the big 21-year-old German center locked up on a long-term deal, they may have to move Nugent-Hopkins, who is signed through 2020-21 at $6 Million per season and may not have enough room to add significant complimentary players over the next few years.

Lou Lamoriello joined the Leafs after the deal that sent Phil Kessel to the Penguins for a first round pick and prospect Kasperi Kapanen. The 74-year-old Hall-of-Famer has successfully hastened the transition in Toronto by utilizing Maple Leaf Sports and Entertainment’s financial might to move out contracts, use cap space to take on salary for future assets and get players signed to cost-effective extensions.

The nine-player deal that sent Dion Phaneuf to Ottawa was Lamoriello’s signature achievement. Toronto took a short-term hit of over $9 Million by taking Colin Greening, Jared Cowen and Milan Michalek from Ottawa, but cleared the remaining four years of Phaneuf’s deal at $7 Million per season.

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Lamoriello has been able to lock up Nazem Kadri ($4.5 Million x 6 years), Morgan Rielly ($5 Million x 6 years), Frederik Andersen ($5 Million x 5 years) and Nikita Zaitsev ($4.25 Million x 7 years) at market value or for slightly less.

Along with Matthews, Marner and Nylander being on their entry-level deals, this enabled Toronto to go out this summer and sign veterans Patrick Marleau, Ron Hainsey and Dominic Moore on short-term deals as support players.

The expiring contracts of James van Riemsdyk, Tyler Bozak and Leo Komarov give Toronto nearly $30 Million in available cap space next summer, and while most of that could be spent on locking up their young core group, Lamoriello’s ability to get players signed to more economical deals, and the Leafs prospect pool churning out NHL-ready talent like Kapanen, Bracco and Dermott, give them a leg up on the Oilers moving forward.