Until last offseason, this era of Toronto Raptors basketball was known for—and ultimately derided for—its consistency. Nearly two decades of irrelevance gave way to five straight seasons of playoff appearances and new franchise records, but no matter how much editing or re-editing was done to the supporting cast, each and every edition of the team was stopped short before the NBA Finals. (LeBron James is a fickle bitch.)
With the potential of the core maxed out, the Raptors risked it all for one season with the kind of superstar who could replace James as the trump card in the Eastern Conference. And while it took some untimely injuries from their competition and a few lucky bounces—four, to be exact—along the way, the gamble paid off better than anyone could have dreamed: with Kawhi Leonard hoisting the Larry O’Brien Championship Trophy, and another Finals MVP, after the Raptors beat the Warriors in the Finals in six games.
Anything that happens this offseason is probably worth the highs of this postseason, but if the Raptors hope to transition from one-hit wonder to a dynasty of their own, plenty of franchise-altering decisions await. Here are the three major questions facing Toronto in perhaps its biggest offseason since Masai Ujiri took over in 2013.
Will Kawhi Leonard re-sign?
It all comes down to this. Ujiri replaced a vital organ on the best team in franchise history with a machine in order to finally break through in the Eastern Conference. The surgery worked miracles, but Toronto could still wind up feeling the long-term repercussions of risking the future for this one-season window if Kawhi wants out.
Until about two weeks ago, it was widely assumed that Leonard would pack his parkas away for good and flee to the West Coast, where he spent the first two decades of his life. The Los Angeles Clippers stationed officials at Leonard’s games in Toronto, a mere 2,500 miles away from their home base in Playa Vista, throughout the regular season, and quietly operated as if the three-time All-Star were already in hand. The Clips have done everything in their power since to make themselves appealing to Leonard—pushing the Warriors like no team ever has before in the first round of the playoffs, reportedly trying to buy the rights to Leonard’s old logo from Nike, paying a hefty fine for making a pretty banal sports opinion. But all of it may pale in comparison to the history Leonard made this postseason.
There’s a future to be had in Toronto, too. If Leonard can suppress his aversion to cold weather—he did say snow looked cool once!—the Raptors can offer something the Clippers and most of the other likely suitors probably can’t: a future All-Star just entering his prime. Pascal Siakam has arrived, and at 25 years old, he’s a player with whom you can compete for titles now—unlike, say, Shai Gilgeous-Alexander (20) and Landry Shamet (22). The question—one bolstered by recent rumblings of Leonard staying put on a short-term deal—is how long the rest of the roster can compete along with them. Kyle Lowry is 33, Marc Gasol is 34, Danny Green is 31 (and a free agent), Serge Ibaka is 29. Ujiri has a flair for mining the fringes of the league for quality contributors, but turning over half of a championship rotation while remaining competitive is Sisyphean-level work.
Ujiri wanted to hard-reset when he took the Toronto job; it seems like he’ll finally get his chance, if not this offseason then in the ones to come.
Will Marc Gasol opt in?
It’s been a treat to see Gasol, one of the last vestiges of one of the most fun teams in recent NBA history, make one last Finals push alongside all of these skilled, versatile players in Toronto—it’s kind of like a city dog living out its golden years on a farm. But as dominant as Gasol has been at times in his career, the elder statesman of Grit and Grind looked more like a specialist among the stars of today in the playoffs (9.4 points per game). Gasol, 34, still affects the game in noticeable ways—he had the Raptors’ best net rating in the regular season, and many a yarn has been spun about his stonewalling of Embiid in Round 2.
But as helpful as that player is, he’s not worth $25.6 million. So it’s probably a forgone conclusion that Gasol will exercise his player option for next season. If Leonard stays, Gasol is savvy enough to still be effective in a high-priced timeshare at center with Ibaka (due $23.3 million next season). But a Leonard exit and an ensuing rebuild might convince Gasol to go ring-chase elsewhere—San Antonio or Golden State (which could lose Kevon Looney and DeMarcus Cousins this summer) would be great fits. Even in that case, he’d be better off opting in and forcing the Raps to buy him out, à la Dwyane Wade in Chicago.
Is Pascal Siakam a max player?
Siakam’s regular-season averages of 17 points on a 59.1 effective field goal percentage, seven rebounds, and three assists will likely earn him the Most Improved Player Award—a nice honor, albeit one with a nebulous definition. But his postseason breakthrough (18.7 points on 50 eFG%, 7.0 rebounds, and 2.7 assists) suggests a player with a far greater ceiling. A year ago, Siakam was just another schlub in LeBron’s way to the Finals. Now he looks like one of the conference’s best two-way players—the next Kawhi, even. The question is whether he’ll get paid like it.
As good as Siakam has been, you wonder whether he can have the same success as the focal point of the Raptors offense. On one hand, he isolated more than any Raptor other than Leonard this season, so he’s used to creating his own shot. On the other hand, he no-showed in a few crucial situations, including in a Game 2 loss to the Warriors, and he’s still learning how to get others involved (though, so is Kawhi). So while Siakam’s agent has every right to ask for a max extension this offseason, the Raptors may be better off telling him to earn it next season; worst-case scenario, they max him the following summer. The risk in playing hard ball is often upsetting a star player, but Siakam is already 25; Toronto may be better off not being the team to sign him to a third deal anyway.
