Their core hit a ceiling after facing the same playoff fate despite catching every break last year, so Raptors president Masai Ujiri traded two years of certainty with DeMar DeRozan for one year of championship potential with Leonard.
The downside is obvious. Almost everything from Leonard's health to his motivation was so uncertain that even the infallible San Antonio Spurs punted the challenge. But with the Celtics and 76ers destined for East supremacy, Ujiri had to go all-in.
The upside is undeniable. Toronto won 59 games last season, removed the limitations imposed upon the team by DeRozan, and acquired the best player in the conference. Raptors fans are still mourning the departure of their franchise player, but if Leonard buys in, they'll soon be rooting for a legitimate Finals contender.
Shedding DeRozan allows the Raptors to finally execute the 3-and-D basketball that has characterized the last eight championship winners.
Toronto's lineup will be interchangeable on defense with seven wings standing between 6-foot-4 and 6-foot-9, while also fielding eight shooters that hit over 36 percent from deep last season. The supporting cast built to cover for DeRozan's deficiencies happens to perfectly complement the best two-way player in the game. No team will come close to Golden State, but the Raptors have the best 3-and-D roster of the other 29 teams.
The transition should be seamless on offense, as Leonard can comfortably step into DeRozan's role. Both players are score-first wings, but Leonard is a better shooter, which allows him to play more off the ball. DeRozan almost exclusively operated out of the pick-and-roll last year, and while Leonard will also initiate the offense, he can contribute without the ball in his hands.
DeRozan's inability to hit 3-pointers cramped spacing - especially in the playoffs, when teams schemed against his weakness. He failed to hit a single triple in three playoff series against Cleveland, and teams are happy to leave him open. Leonard, on the other hand, is a career 42.7 percent shooter from deep in the playoffs and is adept at curling around screens as a spot-up threat.
This trade makes a world of difference on defense. DeRozan routinely lost focus on even the most basic of assignments as he tried to conserve his energy for scoring, whereas Leonard is the best on-ball defender since Scottie Pippen. Role players turned into stars against DeRozan; Leonard turns stars into role players.
Not having to hide DeRozan also unlocks more flexibility at other positions. It wasn't palatable to play both DeRozan and C.J. Miles in the past since they're both minus defenders on the wing. The same went for DeRozan and Jonas Valanciunas, since the lumbering Lithuanian wasn't quick enough to cover for DeRozan's lapses. By turning the shooting guard position into a strength, the Raptors can maximize their scorers because they should field plus defenders at almost every other position.
Switching will also become an even more prominent aspect of Toronto's defensive identity. Leonard can guard just about anybody, while Kyle Lowry, Delon Wright, Pascal Siakam, OG Anunoby, and newcomer Danny Green can comfortably switch onto any position save for center. The Raptors can also play an elite defensive rebounder in Valanciunas to anchor their small-ball lineups, or opt for more mobility and shot-blocking with Serge Ibaka at center.
Leonard also solves the Raptors' longstanding inability to defend big wing players. It wasn't just LeBron - even the washed-up remains of Paul Pierce and Joe Johnson torched them. DeMarre Carroll and P.J. Tucker were serviceable stopgaps, but neither compared to a two-time Defensive Player of the Year. Toronto will need to get through some or all of Giannis Antetokounmpo, Ben Simmons, and Gordon Hayward to win the East, and Leonard will be crucial in those assignments.
Philadelphia had the chance to get into the mix for Leonard, but it made embattled rookie Markelle Fultz untouchable in trade talks, and now Leonard's suiting up for a division rival.
Despite an underwhelming summer, the Sixers are expected to make a huge leap based simply on internal growth. And while it's true that Simmons, Joel Embiid, and perhaps even Fultz boast All-NBA talent, each prospect carries fundamental limitations. Until those issues are fixed, the Sixers will remain an intimidating lockdown defensive outfit limited by the absence of a true No. 1 option on offense.
Simmons, for one, needs to figure out which hand he should shoot with, then develop a jump shot. He enjoyed a phenomenal rookie campaign, yet his flaws were laid bare by the Celtics, who dared him to shoot. He'll continue to get the Rajon Rondo treatment until he shows some willingness to shoot a wide-open jumper.
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Fultz has the same problem, only worse. His shooting coach openly said he suffered from "the yips," and the scant training videos that have emerged from their workouts only highlight his hops and not his form. He's a nonfactor until he regains his confidence, which won't be easy after his private business was accidentally made public through Bryan Colangelo's burner accounts.
The responsibility of being the No. 1 option falls on Embiid, but he's not polished enough for that role. At this point of his development, he's similar to where DeMarcus Cousins was on offense in his early years. He's capable of dominance but is too inefficient and unpredictable to carry an elite offense. Embiid shot just 48 percent from the field and 31 percent from three last year, while averaging 4.4 turnovers per 36 minutes, which speaks to issues of endurance and focus.
Toronto also happens to match up nicely with Philadelphia at every position. Valanciunas is lead-footed, but he's as strong as an ox and should neutralize Embiid in the post, and Ibaka isn't a bad Plan B. Simmons is a wrecking ball, but he'll have a hard time bullying a two-time DPOY in Leonard, and Wright was surprisingly successful in that assignment last season. Chasing JJ Redick around screens will be exhausting, but Lowry and Fred VanVleet combined to smother a tougher version of Redick in Bradley Beal during last year's playoffs. Dario Saric is a nice third option, but he largely gets his points as a tricky tweener exploiting mismatches, and Toronto is loaded with versatile stoppers between Green, Anunoby, and Siakam.
Toronto would ultimately hold the advantage in offense in a playoff series against Philadelphia. The Raptors ranked third in offensive rating during the regular season, and they sustained that efficiency and finished second to Golden State in postseason offense. They have the best scorer in Leonard, more ball-handlers who can create, and with only Wilson Chandler replacing playoff heroes Marco Belinelli and Ersan Ilyasova, the Raptors will also have more shooters than Philly.
They weren't even criticized for holding their assets and sitting out the Leonard sweepstakes because their team is already special. But it won't be a walk in the park for head coach Brad Stevens to sell his breakout performers on smaller roles while reintegrating two high-usage scorers.
Stevens will first have to decide who comes off the bench between Hayward, Jayson Tatum, and Jaylen Brown. Benching Hayward would be impossible based simply on his maximum contract, while limiting the development of either Tatum and Brown should give the Celtics serious pause. Stevens could skirt the problem by starting all three, but that risks overburdening 32-year-old Al Horford with the small-ball center role.
The tougher sell will be for Terry Rozier to accept a diminished role during a contract year. Rozier was one of the breakout stars for the Celtics in last year's playoffs, and while he was nowhere near the scorer that Irving was, he was a substantial upgrade on defense. Now he'll have to return to an overstocked bench that also includes Marcus Smart on a new deal.
An excess of talent shouldn't be a problem, though, as great coaches turn depth into versatility. Stevens is as creative as they come, and has consistently fostered cohesive locker rooms in Boston. With a strong vet like Horford by his side and a championship to chase, Stevens should have everyone motivated even if they're playing fewer minutes.
As things stand, Boston narrowly holds the edge over Toronto if both teams are healthy. Lowry is a more well-rounded contributor, but Irving's way more accomplished in the playoffs. Green is a strong defender, but Tatum is a far more dynamic scorer. Horford is simply better than any big on the Raptors' roster. The only advantage would be Leonard over Hayward, but even that's not a huge mismatch. Stevens is also a Coach of the Year candidate, while Nick Nurse is unproven outside of the G League. Toronto could always make an in-season acquisition, but the Celtics have better picks to offer.
But as the Raptors know all too well from their battles with LeBron, the best player can beat the better team in a playoff series. Last time he was healthy and motivated, Leonard had the Spurs up 25 points on Golden State, and Boston isn't on that level. It might have been forgotten while Leonard's reputation was dragged through the mud, but he's a unanimous top-five player in the league when healthy, and his absence turned the Spurs from legitimate contenders into first-round fodder. By the same token, it's not implausible that he can single-handedly push the Raptors ahead of a more talented team in Boston.
That's the gamble Ujiri took. And if he can get Leonard to buy in, the Raptors will have their best shot of making The Finals in franchise history.
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