Toronto Raptors' Bold Gamble for Kawhi Leonard in 2026-27
The deal still isn’t done. That’s the first thing.
With training camp less than three weeks away, Kawhi Leonard is technically still a Los Angeles Clipper, even as the ground has shifted under that franchise in ways that would make any owner’s stomach turn. Five draft picks stripped. A $30 million fine. Lengthy suspensions looming over Steve Ballmer and his top lieutenants after the NBA’s salary-cap circumvention investigation.
Leonard’s punishment? A $700,000 fine — a slap compared to the money he pocketed through the bogus endorsement deals the Clippers arranged. And yet he’s poised to walk into a rich contract extension in Toronto. You can imagine how that plays in Ballmer’s head.
But around the league and inside both organizations, the tone is clear: there’s no panic about this trade collapsing. People close to the talks still expect Leonard to be a Raptor sooner rather than later.
The holdup is structural, not emotional. The Clippers must formally install a new team governor and a top basketball decision-maker to sign off on the transaction. With president of basketball operations Lawrence Frank suspended for six months, general manager Trent Redden is expected to slide into the lead role — fitting, since he’s the executive who steered the Leonard-to-Toronto negotiations in the first place.
The framework hasn’t changed: Leonard to the Raptors, Brandon Ingram and Gradey Dick to Los Angeles. Toronto sends two unprotected first-round picks, a first-round swap and two seconds — the kind of draft capital the Clippers desperately need and no other suitor has been willing to match.
There’s another key piece: Leonard has made it abundantly clear that the team he wants to extend with is Toronto. For everyone else, that turns him into a one-year rental. That reality has chilled any serious late bids.
So the expectation stands: the deal happens. The date is the only mystery.
From Cleveland heartbreak to an Eastern arms race
When we last saw the Raptors in meaningful action, they were walking off the floor in Cleveland in early May, beaten in Game 7 of a first-round series that felt like both a gut punch and a signpost.
They had trailed 0-2 to a heavily favoured Cavaliers team that went on to reach the Eastern Conference finals. They did it without Immanuel Quickley, sidelined with a hamstring injury, and with Ingram limping through an ankle issue that later required surgery while being bullied by a defence he couldn’t solve.
The series loss stung. The response inside the organization was bolder than anyone expected.
Toronto looked at a 46-win season, a playoff return for the first time since 2021-22, and a near-upset of a conference finalist and decided that wasn’t a ceiling — it was a runway. So they pushed their chips in on Leonard, a 35-year-old with a medical file as thick as a playbook, and screamed something loud into the Eastern Conference:
We’re coming now.
The timing is ruthless. The East has never looked more unforgiving. The New York Knicks just rolled through the league and are deservedly title favourites. The Philadelphia 76ers somehow emerged from free agency and the trade market with LeBron James, Jaylen Brown and a fortified bench. The Miami Heat landed Giannis Antetokounmpo.
Boston and Cleveland are still there, mean and dangerous. The Indiana Pacers, Eastern champs in 2025, get Tyrese Haliburton back and expect to bite again. Detroit just won 60 games. Atlanta, Orlando, Charlotte, and a revamped Washington are all chasing playoff oxygen.
Toronto’s surge last season came from pounding weaker teams. There won’t be many soft spots now.
So can they win it all with Leonard back in the fold? That’s the dream, but it’s also a steep climb. Even if Leonard delivers peak production, an NBA title — or even a Finals berth — might be too ambitious in this landscape. A top-four finish in the East, given the arms race around them, would be a serious achievement.
Leonard or Barnes: whose team is this?
Ask on instinct and you say Kawhi Leonard is the Raptors’ best player. The numbers back you up: he’s coming off one of his finest seasons, averaging a career-high 27.9 points per game for the Clippers and earning his seventh All-NBA nod.
But the story in Toronto is no longer that simple.
Scottie Barnes has arrived.
Last season he made first-team All-Defence for the first time, then detonated in that seven-game war with Cleveland: 24.1 points, 8.6 assists, 6.1 rebounds, 1.7 blocks, 1.1 steals per game. He played with a relentless, all-court fury that screamed future All-NBA, maybe even MVP consideration if he can bottle that level from October to April.
Here’s the Raptors’ best-case scenario in one line: Leonard repeats his Clippers production, and Barnes still has a real claim as the team’s top player.
If that happens, Toronto doesn’t just become dangerous. It becomes a problem.
Last season’s peak: one bounce, then another
For the first time in a while, Raptors fans had a season they could enjoy in chapters, not just isolated nights.
There was the nine-game winning streak in November, part of a blistering run of 13 wins in 14 that reset the tone after a shaky start. There was a trip to the NBA Cup quarterfinals, a road win in January over defending champion Oklahoma City, and a dominant two-game home sweep of the Miami Heat in April that locked in a top-five seed.
But one moment towered above the rest.
Game 6 against Cleveland, facing elimination at Scotiabank Arena. Overtime. Clock ticking down.
RJ Barrett, the kid from Mississauga, rose up for a three that hit the back rim, shot what felt like 12 feet into the air, hung there with the season, then dropped straight through with 1.2 seconds left. The building exploded. It was the loudest the arena had been since Leonard’s own four-bounce miracle against the Sixers in 2019.
Different player, different decade, same electricity.
The cracks beneath the surge
The season wasn’t spotless. Early on, it was ugly.
Toronto opened 1-4, with some heavy losses that had nerves jangling. The November heater buried that start, but another issue lingered: the Raptors couldn’t beat the league’s best. They went 1-12 against the top four teams in the East and 1-11 against the top six in the West.
Their playoff fight against Cleveland eased some of that concern. Leonard’s arrival is supposed to erase more of it.
The most worrying storyline, though, wore No. 19.
Jakob Poeltl’s season never really got off the ground. Back problems in training camp bled into the schedule. He played only 46 games and rarely looked like himself. When the playoffs came, he slid to the fringes of the rotation.
All of that would be concerning on its own. It’s magnified by the calendar and the cap sheet: Poeltl turns 31 next month, and his three-year, $84 million extension doesn’t even start until this season. Toronto needs him to bounce back. There’s no easy way out of that contract if he doesn’t.
New faces, familiar core
Strip away Leonard and this Raptors roster looks largely the same, by design. Darko Rajakovic returns for his fourth season with a staff that’s barely changed. The one significant addition is Stephen Silas, the former head coach sliding in as a respected assistant to replace James Wade.
Once the Leonard deal is finalized, Toronto will have 13 guaranteed contracts. Sitting just under the $209 million first apron and hard-capped by the trade, they’re expected to carry only 14 players, the league minimum.
Two names stand out on the fringes.
Rookie Allen Graves turned heads in Summer League with his versatile, composed play. Kyle Anderson, now 33, arrives to take on some of the leadership load Garrett Temple carried so naturally — with the added benefit that Anderson can still give you real minutes.
Who’s gone, and who’ll be missed?
Assuming the Leonard trade closes, Ingram and Dick are out. On paper, that’s a lot of talent. In reality, the Raptors believe the upgrade is obvious.
Ingram made the All-Star team and led Toronto in scoring, but Leonard is better almost everywhere on the floor and has his own injury flags. Dick, after a promising second year, stalled badly. By the time the playoffs rolled around, he had been jumped in the rotation by Ja’Kobe Walter, Jamison Battle and even two-way guard AJ Lawson.
At 22, well-liked and eager for a reset, Dick should get chances with a rebuilding Clippers team. It’s a clean break for both sides.
Temple has moved from unofficial coach to official one, joining Dallas’ bench. Big-man specialist Mike Batiste has returned to Europe as an assistant with his former EuroLeague club. Lawson, after four years chasing a permanent NBA spot, is heading overseas as well.
The next leap: Walter, Murray-Boyles and the kids
If Toronto is going to justify this all-in push, the stars can’t do it alone. The supporting cast has to grow with them.
Start with Ja’Kobe Walter.
The third-year wing quietly transformed after the All-Star break, averaging nearly 10 points per game, drilling 47.6 percent of his threes and swiping 42 steals in 27 games off the bench. His defence is still catching up, but if that shooting holds, he can raise the Raptors’ floor in a hurry.
Then there’s Collin Murray-Boyles.
The second-year big man spent the season battling thumb injuries and still emerged as arguably Toronto’s second-best player in the playoffs, anchoring possessions with his defence and energy. Give him a healthy hand and another year of experience, and he doesn’t just raise the floor — he tugs at the ceiling.
Spotlight on Rajakovic and Quickley
The feel-good, overachieving phase is over. With Leonard in the building, Barnes entering his sixth season and a projected starting lineup making $173 million, the tone around Rajakovic changes.
He’s no longer shepherding a teardown or nurturing an upstart. He’s managing expectations.
Every rotation choice, every late-game play call, every rest day will be judged against the standard of a team that has paid to contend, not just participate.
And then there’s Quickley.
When the Raptors sent OG Anunoby to the Knicks, Quickley was the centrepiece of the return. Barrett has thrived in Toronto colours, playing the best basketball of his career. Quickley, by contrast, has been ordinary and often hurt.
Anunoby already owns a ring. If the Raptors plan on making real noise now and in the years to come, Quickley has to prove he can run a high-ambition team, night after night, without breaking down. The pressure on him is real and immediate.
Circle these dates
If you’re looking for early theatre, it doesn’t get much better than Nov. 2 at the Intuit Dome.
Toronto visits the Clippers. Leonard walks back into the building that mortgaged a decade of first-round picks and Shai Gilgeous-Alexander for him and Paul George, only to cash it in for one thin Western Conference finals run.
Booing feels inevitable. Load management jokes feel inevitable, too — the Raptors play the Clippers on the second night of a back-to-back. Will he even suit up? That’s part of the intrigue.
November doesn’t ease up. Toronto hosts the defending-champion Knicks in a rare two-game set on Nov. 15 and 17, then heads to Detroit on Nov. 20 for an NBA Cup game that could decide whether they reach the knockout stage.
Victor Wembanyama and the Spurs hit Toronto on Dec. 16. LeBron and the Sixers arrive Jan. 10. Gilgeous-Alexander and the Thunder visit on March 10.
No. 7 to the rafters
On Jan. 10, before LeBron steps onto the Scotiabank floor, another giant moment will unfold.
Kyle Lowry’s No. 7 will rise to the rafters, joining Vince Carter’s No. 15 as the second jersey the franchise has ever retired. The "GROAT" — the greatest Raptor of all time — will see his number hang over the court where he became the heartbeat of a championship team.
The ceremony will cap a full Lowry celebration. A celebrity golf tournament on Sept. 18, a block party at Jurassic Park, a fundraising gala on Sept. 19 — a proper send-off for the man who left as the franchise leader in assists, steals, three-pointers, wins and playoff wins.
By the time that banner settles into place, the Raptors will know exactly what they’ve signed up for with Leonard, what they have in Barnes, and how far this version of Toronto can really go in an Eastern Conference that no longer waits for anyone.
