It’s September 25, 2000, a timestamp of great underestimation from the entire league of what a young Paul Pierce was capable of becoming.
Kawhi Leonard’s management team have arranged meetings with four franchises regarding his basketball future.
He will meet with the Lakers and Clippers early next week, followed by the Knicks the following week and then the Raptors will get the final meeting. Where Leonard ends up will have a large impact on the league as he is one of the few players who can elevate any team to title contender.
The Toronto Raptors took a gamble trading for Kawhi Leonard in July 2018. Typically, teams had been apprehensive to trade for superstars coming to the end of their contracts, especially if they had not given a strong indication they would be willing to re-sign at the season’s end. The fear was that Leonard would walk away from the Raptors this off-season to sign with one of the Los Angeles-based franchises, his hometown, leaving them with nothing.
The Raptors, however, approached the situation from a new perspective. Despite being one of the east’s elite teams, winning a total of 263 games in those between 2013-2018, more than any other team in the east, they had struggled in the postseason, making only one conference final.
The franchise boasted a very strong team built around point guard Kyle Lowry, shooting guard DeMar DeRozan and a deep bench, however, it had become apparent this iteration of the Raptors was good enough to dominate the regular season but couldn’t contend for a title. The team management essentially had three options: stick with its current squad and hope something somehow changes endogenously, sell its assets and start over with a full rebuild or swing for the fences taking a chance on a game-changing superstar.
The Raptors figured they had nothing to lose. Trade for Leonard to build a genuine contender and in the process of doing so and conduct a year-long pitch to keep Leonard in Toronto. If things go to plan, not only will they have achieved what they set out to, they will have made a very strong basketball case to Leonard as to why he should stay. If they do not work out, and he leaves, they simply begin the rebuilding process one year later than otherwise.
As it turns out, things did work out for the Raptors, who on the back of that trade are now NBA Champions. Toronto are now favourites to re-sign Leonard after having given him a platform for team success, an outstanding team culture and being attentive to his individual needs (rest and conditioning). However, Leonard will be conducting his free agency meetings in LA and will be meeting with both the Clippers and Lakers in addition to the Raptors.
Superficially it might seem absurd for Leonard to consider leaving a championship team, however, these meetings make a lot of sense and not just because he has been explicit in seeking a homecoming.
Kawhi’s supporting cast in Toronto is ageing. Lowry is 33 and struggled to find consistency in his scoring throughout the playoffs. Marc Gasol is 34 and is showing clear signs of decline as he ages. Serge Ibaka is 29 and isn’t the player he was during his time at the Oklahoma City Thunder. Danny Green is 32 but may not return in free agency.
Leonard, who is 28 years old and very much in the prime of his career, may have some significant reservations about signing a long-term contract with the Raptors. Pascal Siakam had a breakout season and won the NBA most improved player award. He has great potential but is already 25 and projects as a Draymond Green type player, an elite third guy, rather than a superstar in his own right.
Other young players are either still unknown quantities such as OG Anunoby or excellent role players like Fred VanVleet. It isn’t necessarily clear what the next generation of the Raptors will look like.
It is not out of the question that Leonard will look at the Raptors roster and wonder if the championship window has closed just as soon as it opened. The Raptors’ biggest leverage is that they are the only team that can offer Leonard the full max contract of five years.
However, if he doesn’t want to be there in five years’ time this advantage goes out the window. If he does come to that conclusion, both the Lakers and the Clippers will be throwing four-year max contract offers at Leonard and both can make compelling cases for basketball fit and lifestyle.
The Clippers have positioned themselves as a championship team that simply needs its superstar. After trading away the team’s leading scorer Tobias Harris to the 76ers to begin a tanking process the team continued to win and went on to take a healthy Warriors to six games in the first round of the playoffs.
Danilo Gallinari gives Leonard a second scorer, Montrezl Harrell is the prototypical modern centre, a high energy guy who runs the floor, defends and plays with heaps of energy. Lou Williams is the three-time NBA sixth man of the year. Shai Gilgeous-Alexander had an outstanding rookie season and projects to be an elite defender and capable point guard. Landry Shamet is a knockdown shooter.
Aside from Gallinari, all these guys are on team friendly contracts.
The Clippers are a smart team. Even though their attempt to get out of a playoff series they would likely lose didn’t work, it did get them out of the trouble of having to either re-sign Harris to a max contract or lose him for nothing.
Whether or not Harris is worth a max contract is an area of great debate and is now a problem for the 76ers, while the Clippers are in the running to sign a genuine star.
Finally, recent reports suggest that Leonard and Kevin Durant have been in communication regarding joining forces and the Clippers are one of the few teams that can make that happen.
All this adds up to make the Clippers an attractive landing spot for Leonard for the foreseeable future. Leonard should be confident he can elevate this team to immediate contenders, after all, he brought a title to Toronto in one season.
The Lakers are the other team who will be sitting down with Leonard. The Lakers are not a token participant in this process either. Kawhi specifically requested former Lakers president of basketball operations Magic Johnson attend their meeting. Evidently, this is against league rules, but it shows Leonard is interested in the Lakers and their legacy.
Their pitch to Leonard will be incredibly simple, come home and play basketball with LeBron James and Anthony Davis. After making a trade this week to clear up space to sign a max free agent the Lakers only have three contracted players for the 2019-20 season: LeBron, Davis and Kyle Kuzma, so the on-court side of things is very straight forward.
The only questions Leonard may have will be the Lakers’ ability to find six to eight guys to take minimum contracts to fill out the roster. Off the court, the Lakers will try and sell Leonard on their legacy and bringing him in to revive Showtime with possibly the greatest collection of basketball talent ever assembled.
Although James will be 35 this season, he will remain a force as he plays out the final years of his career with the Lakers and Davis and Leonard will be good enough to be perennial finals contenders no matter who fills out the rest of the roster. This decision will come down to how Leonard and his unique personality will fit with two other superstars and whether he wants to run his own team or be part of a big three.
Whilst Leonard will meet with the Knicks, any chance of him signing there is predicated on them getting either Durant or another major free agent, and even then they seem to be at long odds to secure his services.
My prediction is that Leonard will be going back to Toronto but on a short deal, most likely a two-year deal where the second year is a player option allowing Leonard to move on if he feels the Raptor’s championship potential comes to an end. If he were to leave Toronto, I think it is more likely he joins the Clippers to carve out his own legacy rather than joining up with LeBron and Davis and the circus that comes with that territory.
No matter what happens, Kawhi Leonard will be contending for a title in 2020.