How winning NHL Draft Lottery could set up a San Antonio Spurs-esque future for Maple Leafs
“It has been said that history repeats itself. This is perhaps not quite correct; it merely rhymes.” – Theodor Reik
On that fateful night in New Jersey, everyone knew that the odds were stacked against the Leafs keeping their first-round pick as it was more likely that they would hand the sixth overall pick to the Boston Bruins. All fans were hoping for was that the team could remain in the top five so there could be some silver lining to what was otherwise a difficult year. Not only were they able to remain in the top five, the Leafs were gifted a miracle from the hockey gods by having the exact combination needed to secure the first overall pick.
When looking at this scenario that the Leafs lucked themselves into, it’s hard not to think of the parallels between that and what the NBA’s San Antonio Spurs experienced in the late 1990s.
Back in the 1980s, the Spurs were a team that had small bursts of success but were never able to sustain them for a long period of time. Things took a downturn in the latter half of the decade before bottoming out in 1986-87, which resulted in them winning the draft lottery and the rights to select center David Robinson.
His NBA debut was delayed by two years due to serving in the military, but the Spurs’ fortunes immediately changed as soon as he was finally ready to play. San Antonio became a perennial playoff contender and was typically among the top teams in the NBA for the next seven years, but the Spurs could never find the breakthrough in the playoffs. Despite securing plenty of individual accolades including league MVP, NBA fans of that time thought of Robinson as a choke artist and felt that no team could win a title with him.
An injury-plagued 1996-97 season did not do him any favours in terms of his reputation, with the Spurs collapsing to the league basement a year after losing in the second round of the playoffs. But with a stroke of luck, they won the draft lottery and secured the rights to select Tim Duncan first overall. With him and Robinson leading the charge, the Spurs returned to the playoffs the very next season and won the NBA title the year after that. From there, San Antonio became a powerhouse of the league and went on to win four additional championships with Duncan as the face of their franchise after having the torch passed down from Robinson.
This brings us back to the Leafs, and there are plenty of similarities between the position they now find themselves in and where the Spurs were back in 1997.
The Leafs had bottomed out the year they won the draft lottery and secured the rights to draft Matthews first overall in 2016. They became perennial playoff contenders as soon as he arrived with nine consecutive playoff appearances, but the team was never able to find the breakthrough in the playoffs. Despite securing plenty of individual accolades including league MVP, NHL fans have labelled Matthews as a choke artist and feel that no team can win a Cup with him. An injury-plagued 2025-26 season didn’t help with his reputation, with the Leafs collapsing to the league basement a year after losing in the second round of the playoffs. But with a stroke of luck, they won the draft lottery and have secured the rights to select one of McKenna or Stenberg.
By no means does this mean the Leafs are destined to win the Cup within the next two years (or multiple Cups for that matter), but their future has been set to have Matthews and McKenna/Stenberg headline the next half-decade before the elder statesman passes the torch to the next face of the franchise. They no longer have to worry about how many more kicks of the can they have left with only Matthews at the helm; they can instead focus on beginning the transition between him and McKenna/Stenberg while continuing to be in contention for the Cup.
Of course, the combination of Robinson and Duncan was not the only reason why the Spurs were able to turn around so quickly. They made smart trades, drafted well, had an exceptional coach in Gregg Popovich, and established a strong culture that has remained to this day. As a result, they were able to field a strong team that was able to regroup and stay competitive, headlined by the likes of Tony Parker and Manu Ginobili forming the new nucleus around Duncan.
Chayka and Sundin have a great starting point in Matthew Knies and Easton Cowan being solid pieces to form a new nucleus around McKenna/Stenberg, but there’s plenty more that they will need to do. It will take executing smart trades, solid drafting, getting an exceptional coach, and building a strong culture that can sustain itself for years to come.
It remains to be seen if the Leafs can indeed pull off something similar to what the Spurs were able to do, but there are enough parallels between the two scenarios that it is not out of the realm of possibility that it could be possible.