30 Teams in 30 Days: Toronto Raptors 2019 Offseason Preview

It’s rare that a team has so much up in the air coming off a championship run, but the Toronto Raptors’ roster (and front office) could look very, very different when it comes time to hang the club’s first banner and hand out rings. It starts at the top with Kawhi Leonard and permeates to up to 60 percent of their starting lineup throughout the playoffs: Leonard, Marc Gasol, and Danny Green can all be unrestricted free agents this summer. In 2020, Kyle Lowry and Serge Ibaka will follow suit, as will Fred VanVleet. All told, the Raptors have two players under contract for 2020-21 at this moment: Norman Powell and OG Anunoby. This sort of extreme volatility is rare for a championship team, who will often mostly run back the same roster as often as they can until the title window shuts for good, but Leonard in particular is the rare star player who may or may not care about what is typically expected of players of his caliber.

Leonard’s free agency will define Toronto’s offseason. He’s has three options, as it relates to the Raptors: leave in free agency for another team, sign a 1+1 in Toronto to keep his options open next year, or sign a five-year contract to solidify his place with the Raptors for the foreseeable future. Each come with their own set of ramifications, with the five-year option obviously being the best for Toronto as a club but not necessarily for Leonard as a player, whether he’s looking to maximize his potential for championships or his career earnings.

Leaving for another team is the nuclear option, as it relates to the Raptors. Depending on how Gasol treats his player option, they might have some cap space to use to sign outside free agents, but it wouldn’t be enough to land a player who can replace what Leonard brings to the court, because, well, there’s nobody in the league right now who can do that. Coming off a season that saw him elevate his game yet again to win a title and Finals MVP, Leonard has a very strong case as the best player in the world. His chief competition would have been Kevin Durant, but he’ll likely miss the entire 2019-20 campaign with an Achilles tear and it’s unknown at this point whether Durant will ever be the same player he was this past season. LeBron James suffered through a lost season with the Lakers, but the last time we saw him in the playoffs, he reminded us just how dominant he can be. Giannis Antetokounmpo should win the regular season MVP (how dumb is it that the league still hasn’t announced their regular season MVP and we’re three days from the draft and two weeks from free agency?), but lost out to Leonard in the Eastern Conference Finals. Leonard, in my estimation, is the best player in the world right now, and it would be catastrophic to lose him, to say the least.

For what they paid to obtain him and the success he brought to the team, the Raptors would still do last year’s trade with San Antonio a thousand times out of a hundred, but as we look forward, it would still sting to see Leonard walk away if you’re in the Raptors’ front office. Every team with max cap space will be banging on Leonard’s door when free agency opens, if not sooner than that, and nobody seems to have a clue what he’s thinking, what he prioritizes, or where he may end up come July.

The other end of the spectrum is a five-year full boat max contract with all the normal goodies – a player option on the final year and a 15 percent trade bonus. This would be the ideal outcome for Toronto, as they’d lock him up for at least another four years and could continue to build out their team to compete for multiple championships during his run with the Raptors. From a team-building perspective, this is also a perfect outcome, as they could use Leonard as the key cog in the transition from the Lowry-Ibaka days into the VanVleet-Siakam era, all with Leonard at the helm as the team’s best player. Even if he decides that he wants to play in Toronto long-term, this isn’t the best path for Leonard.

The middle ground is a 1+1, where Leonard signs on for a max contract with the Raptors this offseason to run it back with the team that just won the title, but instead of a five-year max deal, it’s a two-year deal that allows him to hit the market again next year. Next year’s pay is the same as it would be anywhere, $32.7 million on a projected $109 million salary cap, but Leonard reserves the right to do this entire free agency thing again next year, while also returning to Toronto to defend their recently-won throne. Signing up for another year with the Raptors also lines up perfectly with his veteran teammates, as both Lowry and Ibaka are free agents in 2020, along with Gasol, should he opt in to his $25.6 million contract.

The timing of a 1+1 lines up with a number of his high-profile teammates and it gets him one step closer to ten years of NBA service, which he’ll notch in 2021. At that point, he’ll be eligible for 35 percent of the cap as a starting salary on a max contract, rather than the 30 percent he will undoubtedly earn next season. He’s ineligible for a supermax contract this offseason since he was traded last offseason, so the path to earning the most money he can reasonably make is to sign a pair of one-year contracts this year and next, then sign the big supermax contract in 2021, which will take him through at least his age-33 season. That supermax contract may not be quite as super in 2021, though, unless he’s going to stay with Toronto throughout this process.

If he changes teams this offseason and signs consecutive 1+1s with that new team, they’d still only have Early Bird rights on him and could only sign him to a four-year max contract, though that deal would still come with 8 percent raises and would be quite lucrative. If he stays in Toronto next season and signs another 1+1 with another team in 2020, then that incumbent team wouldn’t be able to offer him any more than the others, as they’d be limited to a four-year max contract with just 5 percent raises under the Non-Bird Exception. Only Toronto will be able to offer him the full five-year max, whether he wants it this summer as a 30 percent max player or in 2021 as a 35 percent max player.

The only way around this would be to sign three consecutive 1+1s, starting this summer, which would put him up for a five-year max in 2022 with whichever team he chose this offseason, but that sort of long-term plan comes with the caveat that he’d be committing to that team for at least seven years (three 1+1s plus four of the five years on a five-year max, since he’d have a player option on the eighth year). He’d reserve the right to change his mind about that plan at any time during the 1+1 years, but maximizing his earnings could look something like that.

Maximizing his championship potential, on the other hand, may not follow quite the same path. There’s still so much to be figured out about how the summer will play out, even though a large domino did fall over the weekend when the Los Angeles Lakers completed their trade for Anthony Davis. The Lakers may turn their attention toward Leonard next, though actually bringing him in seems a bit farfetched for them at this point. The Los Angeles Clippers and Brooklyn Nets will be primary non-Toronto suitors for Leonard, though both teams would have to come up with a plan to pair Leonard with a secondary star before he’s likely to consider either destination his best path toward winning more championships. For now, Toronto is in the lead in this component of his decision, since they already have the team that just won a title around him.

Elsewhere on the roster, Toronto will have decisions to make that cascade downwards from Leonard’s choice. Gasol’s player option will inform the money they have to spend this offseason, as they can open up a touch more than $20 million in space if both Leonard and Gasol decide to move on from the team. It’s certainly not enough to find suitable replacements for both players and won’t put them at the top of anybody’s title favorites list, but as they move into the final years of Lowry and Ibaka’s contracts, it will give them a chance to retool as best they can for a final hurrah before the team is truly passed on to the team’s next generation. If Gasol opts in and Leonard leaves, then that cap space evaporates and they’re stuck with just the mid-level exception, bi-annual exception, and minimum contracts to fill out the squad.

Green’s free agency will be fascinating to watch, particularly if he’s on the move from Toronto. Retaining him on top of Gasol and Leonard would get very expensive very quickly for the Raptors, though they’ve never shied away from paying the tax in the past. How teams value him throughout the league will be interesting to monitor, as the theory of what he brings to the table has sometimes clashed with his actual production. He was seemingly a throw-in to the Leonard trade last summer, at least from San Antonio’s perspective, and he was often not on the floor to close games for the Raptors in the playoffs, but his shooting and lead guard defense should render him a starter-level free agent this offseason and the substantial raise that goes with that designation. Something starting around $15 million a year would make sense for Green, whether in Toronto or elsewhere. If the Raptors are getting the band back together for another title run next season, Green should be a part of that, despite his frustrating game-to-game inconsistencies.

Long-term, the Raptors have very little bad money on their books. Norman Powell spent most of the postseason in their rotation and they’re on the hook for $32.6 million owed to him over the next three years, but outside of that deal, they have nobody on a non-rookie scale contract who stretches past 2019-20. Powell’s not necessarily a negative value on his contract, though his value dips somewhat if he’s asked to take on a larger role. Still, as an eighth man on a championship team, he’s paid just about what you’d expect at roughly $11 million a season.

Masai Ujiri did a wonderful job in 2017 to set up Toronto’s long-term books, when he signed Lowry and Ibaka to three-year contracts and gave the team that window to compete before he was planning to go to the youth movement. As it turns out, he was able to trade for Leonard and Gasol, whose contracts line up with that general timeline and will allow the club to pivot quickly into the next era, with Siakam leading the way. VanVleet can hit unrestricted free agency in 2020, but he’s likely a big part of their plans going forward, as Lowry will be ready to cede the starting point guard spot to him at that point.

There are a lot of divergent paths in front of the Raptors, but they don’t have full control over which path they take. They’ve done everything they can to convince Leonard that Toronto is where he should make his long-term home – they have the best medical staff in the league and managed his injury issues perfectly this season, they won the title in his first year in town, and they should have a sustainable model of success for the remainder of his prime years. Whether that’s enough to sway his decision toward the Raptors remains to be seen, but Toronto will do next to nothing until they get word from the best player in the game today on where he chooses to play next season.