The Kawhi Leonard Sweepstakes: Will the Raptors finally defy the odds?

(By: Jackson Farough)

“If you’re looking to the future, you’re gonna trip over the present” – Kawhi Leonard.

Kawhi Leonard is different than any other player in the NBA. He rarely shows expression, doesn’t care about the money or stardom that comes with playing in the NBA (He still drives an old Chevrolet Tahoe) and could also become the first and only true superstar to choose to stay in Toronto next summer, which would make him even more unique in a sense.

Leonard’s contract situation, along with his future in Toronto, has been a lengthy topic of discussion around the entire NBA this season. It all began when he was traded from the NBA’s version of the New England Patriots over the last 20 years, the San Antonio Spurs, to the Toronto Raptors, a team that has the same amount of division titles as the Spurs do championships.

Leonard is on the last year of his 5-year, $94 million contract that he signed in 2015. At seasons end, he has the chance to exercise his player option and become a free agent, which he most certainly will do.

He’s averaging 27.5 points per game this season, placing him 5th in the entire NBA. Over the last 4 seasons, including this one and excluding last season’s injury-riddled debacle in San Antonio, he’s averaged over 24 points per game. Not to mention his 2014 NBA Finals MVP honour as well as being named NBA Defensive Player of the Year twice, proving that Kawhi truly is a two way NBA superstar. He also has tons of playoff experience, 87 playoff games to be exact, from his time with the Spurs and his appearance in two NBA Finals with them. Thus, he has the chance to become the best Raptor ever, should he choose to remain in Toronto.

So, why would Kawhi Leonard stay? Why would he leave? Here are some reasons for both:

Why would Kawhi go somewhere else in 2019?

  • He has no affiliation with Toronto or Canada (Although he did buy a house in Toronto).
  • He grew up in California, with palm trees and sunny beaches, along with watching the Kobe/Shaq Lakers dynasties growing up.
  • He could join forces with another star, such as Kevin Durant, to form a superteam elsewhere, just like Chris Bosh did.
  • It’s cold here. (Apparently it matters, despite Toronto getting the same weather as New York, Boston, Philadelphia, Washington and any northern city in the US for most of the year.)
  • Canadian dollar value? (It’s a stretch, but you never know.)

Why would Kawhi stay in Toronto in 2019?

  • He could come to love the city of Toronto and all that it has to offer.
  • It’s away from the American media storms that haunt Boston, New York and Los Angeles.
  • Plenty of Canadian endorsement deals. (He recently signed a shoe contract with New Balance, who have 6 store locations in Toronto alone.) Ask John Tavares and Auston Matthews about how lucrative Canadian endorsements can be, especially for superstar athletes.
  • The team is young and talented; they could make the NBA Finals this season which would give him an opportunity to win, something that he continuously states that he wants to do.
  • He can sign for more money with the Raptors than anywhere else, since he would be their own free agent.
  • His own legacy: As mentioned, no superstars have chosen to stay in Toronto to play for the Raptors (DeRozan is not a superstar). Kawhi Leonard could carve his own unique path and transform the Raptors into a long-standing dynasty, becoming the first true NBA superstar ever to do so. Is this something that he cares about? Raptors fans sure hope so.

The Raptors have been a borderline laughing stock of the NBA since their inception in 1995. With 0 championships or conference titles, along with playing in a different country than the rest of the NBA, American news outlets hardly take the Raptors seriously. Colin Cowherd of Fox Sports One calls them the “baby dinosaurs.” Many players don’t like going through customs on the way to Toronto, or the cold weather that sets in from October to April in some years.

Another aspect of this saga is, of course, the idea that the Raptors should be actively recruiting Kawhi all season long. Kyle Lowry, a key player on the Raptors sparked optimism among Raptors faithful with this interaction:


Is this recruiting? It’s banter more than anything else, which occurs in every NBA locker room. As always, it’s hard to get a read on Kawhi in terms of what he’s thinking or feeling, so take this interaction with a grain of salt.

For now, Raptors fans should take Kawhi’s advice and worry about the future later. This season has the looks of being a hell of a fun ride for Raptors fans. Let’s enjoy it while it lasts.

Here’s hoping Kawhi likes Tim Hortons and hockey as much as the rest of us do.

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