I should start by saying it pains even me to be writing this article.
Kyle Lowry, six-time All-Star Point Guard and NBA Champion for the Toronto Raptors, is not unfamiliar with the prospect of leaving Toronto. In 2017’s free agency, Bleacher Report claimed that he had ‘zero interest’ in a return to the Raptors before he ultimately re-signed to a 3-year deal. In the summer of 2018, Lowry was involved in trade rumors alongside long-time running mate DeMar DeRozan, culminating in DeRozan’s move to San Antonio for Kawhi Leonard. Even in 2019, the year the Raptors finally broke through to win the championship, Kyle was again on the block at the trade deadline, where he was reportedly offered in a package deal with Jonas Valanciunas for both Mike Conley and Marc Gasol which ultimately resulted in only Gasol moving.
This year, the conversations feel a little bit more real. With the 34-year old point guard set to hit free agency in the summer of 2021, Toronto is faced with the question of culture versus asset management. Since winning the championship in 2019, each off-season has been marked by difficult departures of key starters from the championship squad to free agency, losing Kawhi Leonard, Danny Green, Marc Gasol, and Serge Ibaka and receiving no value in return. Apart from Kawhi’s decision to leave, these have all been voluntary sacrifices from Toronto’s front office in order to pursue a max free agent in what was supposed to be a star-studded 2021 summer. Instead, Giannis Antetokonmpo, Paul George, Rudy Gobert, Jayson Tatum and a host of other potential free agents signed long-term extensions with their teams, leaving the Raptors in a tough spot. The roster drain has clearly had a detrimental effect on the Raptors’ rotation, leading to an uncharacteristically middling record halfway into the season. In a tightening belt of middle-of-the road clubs in the East, the team is still well within the playoff race, but the potential for substantial playoff success is clearly limited. For some in the Toronto fanbase, trading Lowry is a way to ensure some type of value in the case that Lowry plans to leave the team in order to pursue another championship. For others, the veteran perspective and leadership which Lowry brings to the table is simply indispensable.
Philadelphia, Lowry’s native city and the current first seed in the East, has been a commonly noted potential destination. Lowry has done as much as he can to distance himself from these rumors, as his agent even outright denied them in an interview with NBA Today. Sooner or later though, the choice will need to be made–most likely as a collective decision between Lowry and the front office. Ideally, should Lowry decide that he would like to leave the team in the summer, he would make them aware prior to the deadline with time to make sure a good deal gets done. More ideally, Lowry re-signs in the off-season for however much money is amenable to both parties. A real win-win, as the Raptors keep their franchise figurehead on board to lead the next generation into his eventual twilight years, and Lowry maintains his value. However, in the NBA, things rarely shake out so cleanly, whether it be through a breakdown in communication between Lowry’s agent and the front office, or a deal on the table too good to decline.
Toronto’s front office has shown themselves to be willing to make a big move when the time is right, even when toes need to be stepped on. When the front office traded DeMar DeRozan for Kawhi Leonard in the summer of 2018, the fallout was immense and bitter, for good reason. DeRozan had in many ways been revered in Raptors fandom as Lowry is now, but was blindsided by the trade in the dead of night. While the move has been rightly canonized as a perfect gamble by the front office, it undeniably left a bad taste in the mouth of players both on the team and from players observing afar, with Lowry taking special offense. While aggression of the front office has clearly paid out dividends, it has also been a crucial element of the Raptors’ struggles to retain their pieces. Now, with Lowry’s future in question, the team, front office, and fanbase all stare down what could be the ultimate price for their ambitions.