Kawhi Leonard Trade: Raptors’ High-Stakes Bet for 2026-27
The deal is still not done. That’s the first thing. With training camp less than three weeks away, Kawhi Leonard remains, on paper, a member of the Los Angeles Clippers.
On the ground, though? The anxiety in Toronto is surprisingly low.
The Clippers are in chaos after the NBA’s salary-cap circumvention investigation: five draft picks docked, a $30 million fine, and looming lengthy suspensions for owner Steve Ballmer and his top two executives. Leonard, meanwhile, walks away with a $700,000 fine — a slap on the wrist compared to what he gained from the sham endorsement deals the Clippers arranged — and a likely lucrative extension with the Raptors.
That has to sting in Los Angeles. Badly.
Yet people close to the negotiations remain convinced: the trade sending Leonard to Toronto and Brandon Ingram and Gradey Dick to the Clippers is expected to go through. The holdup is procedural. The Clippers still need a new team governor and a top basketball decision-maker to formally sign off, with president of basketball operations Lawrence Frank suspended for six months and Trent Redden poised to assume the lead role.
The numbers still tell the story. The Clippers need draft capital more than ever; the Raptors have put more on the table than anyone else: two unprotected first-round picks, a first-round swap and two seconds. No other team has come close, and with Leonard making it clear Toronto is where he wants to sign an extension, no rival front office is eager to pay that price for what would almost certainly be a one-year rental.
Redden’s presence helps. He was the executive who steered the Raptors–Leonard talks from the Clippers’ side in the first place. The framework is in place. The motivation is obvious. The expectation is unchanged:
The deal gets done. The timing is the only mystery.
From Cleveland heartbreak to a bold leap
When we last saw the Raptors in meaningful action, they were trudging off the floor in Cleveland in early May, beaten in Game 7 of a first-round series against the Cavaliers.
It hurt. It also hinted at something.
Toronto had fallen behind 0-2 to a heavily favoured Cavs team that went on to reach the Eastern Conference finals. The Raptors clawed back, pushed the series to the limit, and did it without point guard Immanuel Quickley, sidelined by a hamstring injury, and with leading scorer Brandon Ingram hobbling on an ankle that later required surgery. He also struggled to handle the physical, unrelenting defence thrown at him.
For a franchise that had been drifting around the middle, that series felt like a signpost. Maybe they were closer than everyone thought.
The front office clearly believed it. After a 46-win regular season and that gutsy playoff run, Toronto chose aggression. The Raptors didn’t just nudge forward — they lunged, effectively going all-in on a 35-year-old star with a long injury file in order to keep pace in an Eastern Conference that has become a minefield.
Training camp opens Sept. 29 in Quebec City, with a first pre-season test against Giannis Antetokounmpo and the Miami Heat on Oct. 3. By then, the expectation in Toronto is simple: Leonard will be in uniform, and the window will be wide open, even if only for a short time.
Can this team actually win the title?
That’s the question that hangs over everything. Trading for and extending Leonard at 35, when he’s played just 56 per cent of his team’s games since 2017-18, is the definition of a “win now” move.
But look around.
The New York Knicks are defending champions and enter the season as favourites after a dominant title run. The Philadelphia 76ers somehow walked out of the summer with LeBron James in free agency, Jaylen Brown via trade, and a deeper rotation that shoves them straight into the contender tier. Miami added Antetokounmpo. Boston and Cleveland remain loaded. The 2025 East champion Indiana Pacers get all-NBA point guard Tyrese Haliburton back from injury. The Detroit Pistons just won 60 games. Atlanta, Orlando, Charlotte and even a revamped Washington Wizards group are all charging toward the playoff picture.
Toronto made its move last year by hammering weaker opponents. There just won’t be as many of those.
Even with a peak-version Leonard, pencilling the Raptors into the Finals feels ambitious. A title run would be an overreach on paper. A top-four finish in the East? That’s a more realistic, and still significant, target.
Who’s the best player now: Kawhi or Scottie?
The instinctive answer is Leonard. He’s coming off one of the finest offensive seasons of his career, averaging a personal-best 27.9 points per game for the Clippers and grabbing all-NBA honours for the seventh time.
But Scottie Barnes has kicked the door in.
The 24-year-old forward earned first-team all-defence last season, then detonated in the first round against Cleveland. Over seven games he averaged 24.1 points, 8.6 assists, 6.1 rebounds, 1.7 blocks and 1.1 steals, playing with a relentless, two-way fury that looked every bit like the foundation of a future MVP campaign.
If Leonard simply repeats last year’s production and Barnes still pushes him for the title of “best Raptor,” Toronto becomes a nightmare matchup. That’s the bet the franchise is making: Leonard’s proven stardom, fused with Barnes’ rising dominance, gives them a one-two punch they haven’t had since 2019.
High points: November heat and an RJ Barrett classic
For the first time in years, last season offered a string of genuine highs.
A nine-game winning streak, and a run of 13 wins in 14 in November, set the tone. Toronto reached the NBA Cup quarterfinals. They went into Oklahoma City in January and beat the defending champions on the road. In April, they swept a two-game, baseball-style home series against the Miami Heat to help lock up a top-five seed. They returned to the playoffs for the first time since 2021-22.
One moment, though, towered over the rest.
Game 6 against Cleveland, back at Scotiabank Arena, season on the line. Overtime. Mississauga native RJ Barrett rose up for a three that hit the back rim, rocketed into the air — maybe 12 feet — and then dropped straight down with 1.2 seconds left. Ball through net. Season saved. Arena unhinged.
The bounce instantly drew comparisons to Leonard’s iconic four-rim winner against the Sixers in 2019. Different stakes, different round, same building, same disbelief. Barrett’s shot didn’t lead to a title, but it carved his name into Raptors lore.
Low points: elite teams, a slow start, and a costly concern at centre
The valleys were fewer, but they mattered.
Toronto opened 1-4 with a couple of ugly blowouts, raising early alarms before that blistering November run calmed everyone down. The more stubborn problem was their record against the league’s elite. The Raptors went 1-12 against the top four teams in the East and 1-11 against the top six in the West. Their playoff performance eased some of those worries, and Leonard’s arrival should help in those high-leverage games, but the gap at the very top was obvious.
Then there was Jakob Poeltl.
The veteran centre’s season never really started. Back issues cropped up in training camp, and he finished with just 46 games played, many of them well below his usual standard. In the playoffs he slid to the fringes of the rotation, a jarring turn for a player about to begin a three-year, $84 million extension. He turns 31 next month. For a team tightening its window, that contract and that level of production form one of the most uncomfortable subplots of the season ahead.
New faces, familiar core
Assuming the Leonard trade closes, the Raptors’ roster will look strikingly familiar. The star forward is hardly a stranger in Toronto. The coaching staff remains largely unchanged as Darko Rajakovic enters his fourth season, with one notable addition: former head coach Stephen Silas joins as an assistant, replacing James Wade.
When the Leonard deal is finalized, Toronto will have 13 guaranteed contracts. Because the trade will push them tight to the $209 million first apron and hard-cap them, the expectation is they’ll carry just 14 players, the league minimum.
Rookie Allen Graves turned heads in Summer League with his all-around game. Veteran Kyle Anderson arrives to soak up some of the leadership duties Garrett Temple handled so naturally — with the added twist that Anderson, who turns 33 this month, can still contribute meaningful minutes on the floor.
Who’s gone: Ingram, Dick and a few familiar voices
The outgoing headline names are clear: Ingram and Dick, once the Leonard deal is rubber-stamped.
On paper, Ingram is a significant loss. He was an all-star last season and led the Raptors in scoring. But Leonard is simply better in almost every facet, and Ingram brought his own durability questions even in a year where he logged a career high in minutes for Toronto. If Leonard can manage 60 to 65 games and, crucially, hit the playoffs healthy, the on-court drop-off from Ingram’s departure should be minimal.
Dick never quite followed up on a promising second season. By the time the playoffs rolled around, Ja’Kobe Walter, Jamison Battle and even two-way guard AJ Lawson had passed him in the rotation. The 22-year-old, a popular figure in the locker room, wanted a fresh start and should get more runway with a rebuilding Clippers team.
Temple moves from unofficial coach to official one, joining the Dallas Mavericks’ staff. Big-man specialist Mike Batiste heads back to Greece to rejoin his old EuroLeague club as an assistant. Lawson, after four years on the fringes of the NBA, takes his shot in Europe.
Breakout watch: Walter and Murray-Boyles
Ja’Kobe Walter already had something of a breakout after the all-star break. Now the Raptors want to see if he can do it over 82 games.
The third-year wing averaged nearly 10 points per game and racked up 42 steals in 27 games down the stretch, drilling 47.6 per cent of his threes off the bench. His defence is still developing, but the instincts are there. If the shooting holds anywhere near that level, Walter becomes a floor-raiser for a team that suddenly has real depth on the wing.
Then there’s Collin Murray-Boyles.
The second-year big man was arguably Toronto’s second-best player in the playoffs, anchoring the defence while playing through multiple thumb injuries. His impact around the rim was obvious, his motor relentless. Give him a healthy season and another year of experience, and he doesn’t just raise the floor — he nudges the ceiling.
Where the pressure lands
No one in Toronto will be more closely examined this season than Rajakovic.
For three years, he coached a team in transition — first tearing down, then retooling, then surprising as an upstart. That phase is over. With Leonard in the fold, Barnes entering his sixth season and a projected starting lineup pulling in $173 million, the Raptors are done sneaking up on anyone. Every rotation choice, every late-game decision, every load-management call with Leonard will be parsed.
Quickley feels the heat, too.
He was the centrepiece of the OG Anunoby trade with the Knicks, even if Barrett has been the one to flourish in Toronto so far. Quickley has battled injuries and stretches of ordinary play. Anunoby already owns a ring. If the Raptors are going to matter in May and June again, Quickley has to prove he can run a contender’s offence, hit big shots and stay on the floor.
Circle the dates
The schedule offers drama early.
On Nov. 2, Toronto visits the Intuit Dome for Leonard’s first game back against the Clippers. The relationship between player and franchise in Los Angeles is complicated at best. His tenure cost the organization 10 first-round picks, Shai Gilgeous-Alexander and only produced a single, underwhelming Western Conference finals run. Boos feel inevitable.
There’s also the question that has followed Leonard for years: does he even play? The Raptors will be on the second night of a back-to-back. The load-management whispers will start long before tipoff.
November is loaded with tests. The Knicks come to Toronto for back-to-back games on Nov. 15 and 17. A trip to Detroit on Nov. 20 could determine whether the Raptors reach the NBA Cup knockout stage. Victor Wembanyama and the Spurs hit Scotiabank Arena on Dec. 16. LeBron and the Sixers visit on Jan. 10. Gilgeous-Alexander and the Thunder arrive March 10.
No. 7 to the rafters
One night stands apart from the rest.
On Jan. 10, before the Raptors host James and the Sixers, Kyle Lowry’s No. 7 will rise to the rafters, joining Vince Carter’s No. 15. The “GROAT” — greatest Raptor of all time — will become just the second player in franchise history to have his jersey retired.
The ceremony caps a full-blown Lowry celebration. The club has planned a weekend of events for Sept. 18 and 19, including a celebrity golf tournament, a block party at Jurassic Park and a fundraising gala. It’s a fitting tribute to the guard who retired as Toronto’s all-time leader in assists, steals, three-pointers, wins and playoff wins.
By the time his number hangs permanently over centre court, the Raptors expect Leonard to be back on that floor, Barnes to be chasing the league’s elite, and a new era of contention to be underway.
The question isn’t whether Toronto has pushed its chips in. It’s whether this bold, late-Leonard gamble can punch through a brutal Eastern Conference and force the rest of the league to take them seriously again.
