The Raptors have obviously had more recent post season success of late than the underachieving Leafs. Their championship run in 2019 was an incredible moment for Canadian sports fans. That success, along with the NBA's vastly superior business model, has knocked the Leafs out of the top spot. The Raptors franchise has increased by over 400% in value over the last 10 years. Why can't the Leafs do the same?
Personally, I blame Gary Bettman. The NHL was poised to surpass the NBA in viewership and become one of the truly elite sports leagues in the world. Instead, Bettman elected to sign a horrible TV deal with OLN and force the league into multiple lockouts, killing the momentum hockey had in both Canada and the US. Now one of the premier teams in the league is playing second fiddle to the franchise they share their home arena with in the best hockey city in the world.
Now, it wouldn't be fair to deny the Raptors credit. Masai Ujiri has built an incredible legacy and his gamble trading for Kawhi Leonard was one of the best moves I've ever seen. The Raptors deserve all the credit in the world for the position they now find themselves in.
Of course the real winners here are Maple Leaf Sports and Entertainment, owners of both the Raptors and the Leafs, along with Toronto FC and the Argonauts. To have a Canadian basketball franchise do so well where others (looking at you, Vancouver Grizzlies) have failed is a massive victory, to also have the second most valuable franchise in the Leafs under the same umbrella? That's about as good as it gets.