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Toronto. A city that bustles with the frenetic lights, sounds, and colours of people and cultures from around the world. Canada’s most populous city that’s home to some of the best culinary and entertainment experiences North America has to offer. A city that Hall of Fame NBA player Charles Barkley frequently touts as being his “favourite city in the world,” to the chagrin of his cohorts at Inside The NBA who’ve grown tired of hearing the legendary power forward repeating the phrase for the past decade. And, of course, a city that’s home to the one and only Toronto Raptors. A team that doesn’t just represent a city, but a country (sorry, Team Canada). To be a part of the Raptors means being a part of something that could have you immortalized in not just Toronto’s sports history, but all of Canadian sports history.

So why is it that the team, who’ve been blessed not once but four times with superstars donning their purple, red, and black who could have potentially contended for championships for multiple years, failed to retain said superstars and lost them to relatively inferior teams? Maybe it’s Toronto’s continuously increasing rent prices and overall ridiculous high cost of living? Or possibly the four months of blistering cold that eats away at your soul one degree at a time? Well, I doubt the former would pose too much of an issue for a millionaire NBA player, and the latter can be fixed with a nice winter coat and a good dose of “just suck it up” attitude. Of course neither of those fix Torontonians as a people, who walk around thinking they’re New Yorkers but forget that, at the end of the day, they’re still Canadian, and as such are bereft of all the charm, humour, and quick wits that make New Yorkers bearable. I digress. Back to the point, the question still lingers in my mind: Why can’t Toronto keep its superstars?

Carter

Of all the four players that are going to be listed in this article, Vince Carter requires the fewest words of introduction. Drafted in 1998, Carter had an immediate impact on the then-fledgling Toronto Raptors. But it wouldn’t be until the turn of the millennium that the man nicknamed “Air Canada” would ostensibly put Toronto on the basketball map; giving us what is still considered to be the most electrifying Dunk Contest performance of all time. 

Carter would go on to make multiple All-Star appearances in the following years and his gravity-defying playstyle pushed Toronto to some of their first-ever Playoff successes. Even after his second cousin once removed Tracy McGrady left him for the Orlando Magic, the Raptors were still a formidable team. Unfortunately, a series of injuries led a frustrated Vince to say “I don’t want to dunk anymore” to the media, which as you can imagine brought on much public scrutiny and allegations of him purposefully not playing hard. Couple that with some questionable executive decisions that led to palpable tensions between him and the Raptor’s front office, and eventually Carter’s time in the north would come to an end, with him getting traded to the then New Jersey Nets. 

In the recent Sportsnet documentary series Raptors Delight, Vince would unveil some of his thoughts during these final tumultuous years, saying that he confided in then-head coach Sam Mitchell by telling him “I don’t wanna leave, that’s just how things are going, but I don’t wanna leave.” Yet, even after hearing that his franchise player wanted to keep playing and that he could have a dynamic duo of Carter and a promising young rookie in Chris Bosh, then-GM Rob Babcock still went ahead and made the trade for Vince Carter. Just another example of executives having zero idea of what they’re doing. 

McGrady

Vince wasn’t the first to leave Toronto. Nor did he leave out of his own volition. Neither of those statements is true, however, for Tracy McGrady. Drafted only a year before Carter, McGrady wasn’t the full-fledged superstar and scoring menace he would eventually become in Orlando. However, early inklings of his potential could be seen when he started to receive more playing time after his cousin, Vince Carter, got drafted a year later. 

The two quickly became inseparable and started to gain popularity for their athleticism on the court. Unfortunately, McGrady’s tenure with the Raptors would be short-lived, and Toronto could do nothing about it because they were fighting against the one thing few cities could contend with–a player’s hometown. “Toronto had no chance, bro,” McGrady said in the second episode of Raptors Delight when retelling the story of him being a free agent and having the opportunity to make a dream of playing in his hometown of Orlando come true. Didn’t matter that the Raptors were offering him a max contract irrespective of him only averaging around ten points a game the season before, that’s simply not something you can win against. 

It’s unfortunate, because as Kobe Bryant said in an issue of SLAM Magazine, “He gave up playing in Toronto, which, I think, if he would’ve stayed in Toronto, we probably would’ve played them in the Finals the last two years…I mean, you’re talkin’ about McGrady and Vince. Those two motherfuc*ers can hoop, man. They’d definitely be a championship-contending team.” One can only imagine what could have happened if these two stuck together, then to add someone like Chris Bosh a few years later–that’s bona fide a big-three. Speaking of Chris Bosh. 

Chris Bosh

Known as the “new hope” for the post-Carter era Raptors, Chris Bosh quickly became the face of Toronto–it helped that he kinda looked like a Raptor, too. Known for his Nowitzki-esque mid-range jumper and Hakeem-like post fadeaway, Raptor-era Bosh was incredibly fun to watch. Though slightly undersized with a fairly thin frame, his crafty footwork and smooth shot made racking up twenty-five points a night a regular occurrence. Yet, for as much fun as it was to watch Bosh as an individual player during those late 2000s, watching the Raptors as a team was a different experience. 

The Bosh-led Raptors struggled to make the playoffs during his tenure with the team. When the couple times they did, they were bounced in the first round, rarely winning more than one game. In a 2019 episode of the Bill Simmons Podcast, Chris Bosh opened up about the struggles the team had faced in recruiting free agents. “I remember John Salmons was a free agent and it was between us and Chicago. So I’m like, ‘Yeah, OK. Oh man, if we can get Johnny Salmons we’ll be pretty good…he took less money to go to Chicago. And that’s kind of when I knew it was going to be a lot more difficult being in Toronto,” Bosh explained. 

Interestingly, one element he attributed to Toronto’s continued struggles to attract free agents was customs. “It’s taxes and customs, and they don’t make it easy on you,” Bosh explained. “We’d go in and out of the city a lot. It’s centrally located, so a lot of in-and-out flights. You’re going through customs every time. And we’re in the airport going through customs and that gets kind of old a little bit. They had to give us our boarding pass and tickets and we had to take off our shoes and laptops, and you know, we’re NBA players — we’ve got a lot of jewelry on. We’ve got a lot of stuff.” He would further tell Simmons that he had done the math one season and calculated that he’d spent an extra 26 hours at the airport over a season. Welcome to being just another disgruntled passenger at an airport, Bosh.   

Kawhi Leonard

After years of being unable to move past a seemingly impenetrable force named LeBron James, the Toronto Raptors achieved what many at the time deemed impossible–beating the Stephen Curry, Klay Thompson, and Kevin Durant-led Golden State Warriors to win the NBA Finals. A feat made possible with the help of a monosyllabic small forward by the name of Kawhi Leonard. After months of tension between him and the San Antonio Spurs front office, Leonard was sent up north in a trade that included the Raptor star DeMar DeRozan. Even though General Manager Masai Ujiri was lambasted for the deal seeing as DeRozan was the longest-tenured Raptor at the time and Kawhi’s contract would see him be a free agent after just one season, the deal obviously proved a tremendous success. 

Yet, even after winning a championship, having essentially the entire country of Canada in your corner, and being offered the kitchen sink and more by the Raptors front office, Kawhi Leonard decided his time in the north was done after just one season. “I just wanted to go to a franchise where I could try to help build a legacy,” said Leonard in an interview with GQ in regards to why he chose to leave Toronto for the Los Angeles Clippers. Frankly, I think that’s a bunch of hogwash. He had already helped build a legacy in Toronto and could have continued to cement that legacy by embellishing his other fingers with one or two more rings. No, Leonard simply wanted to go play for his hometown of L.A. And if he couldn’t do that, then he at least wanted Masai and the Raptors to get Paul George – his close friend, apparently – by trading away half of Toronto’s roster. Now he’s struggling to play a full season with the Clippers and Podcast P is struggling to play with another drama queen in Philly.

The Raptors continue to struggle to attract star players, having to resort to either making smart trades to acquire them or developing them through the draft. It seems taxes, customs apparently, and the simple notion of being in another country (a cold one, at that), are all factors in the city not being able to have stars call it home. The team has struggled this season, though there is some genuinely good talent on the roster. Scottie Barnes and R.J. Barret are already getting whiffs of stardom while youngsters like Grady are on their way to joining them. Hopefully, success is a season or two away for this team. And hopefully, Pearson Airport can figure out their customs so that NBA players don’t have to suffer like the rest of us–although it’s kinda satisfying to know that they have to.