TORONTO — Timing is everything in the NBA.
For the Toronto Raptors, the overwhelming question is whether their time is now.
For all concerned, the hope is the giant bet they made on the 2026-27 season will hit and turn the clock back to 2018-19 — or at least 18-19 adjacent.
Plenty of factors were weighed when Raptors general manager Bobby Webster, newly minted five-year contract in hand, pulled the trigger on the trade that repatriated Kawhi Leonard.
In no particular order:
• Seven years after leading the Raptors to the 2019 NBA championship in the greatest one-and-done showing in league history, Leonard remains an all-NBA talent and arguably the best player available in what was an action-packed off-season for player movement.
• The Raptors were going to have to do something with Brandon Ingram, who was heading into a walk year on his contract. The problem was that even after one of the best seasons of his career, it was clear that Ingram’s fit alongside Scottie Barnes remained a question mark, as was Ingram’s ability to excel in the post-season. The Raptors ended up trading him (along with Gradey Dick) to the Los Angeles Clippers in the Leonard deal.
• Even as the Raptors had exceeded expectations with a 46-win season backed up by a strong showing in the playoffs last year, the Eastern Conference wasn’t standing still. If the Raptors didn’t move, they were at risk of falling back into the pack, erasing any progress.
But perhaps the primary reason for the Raptors to go big-name hunting, and take the chance on Leonard at age 35, was that the clock was ticking. The hourglass representing the best chances to win with Barnes as the fulcrum of their team had already flipped over, with the sand trickling in the wrong direction.
Not that Barnes’ ability was diminishing. Quite the opposite. Part of the Raptors' calculation was that at age 25 and in his sixth season, Barnes is at the cusp of delivering all-NBA level play for years to come.
Because the NBA is essentially a hard-capped league with regard to the upper limit of team salaries, the best chance a team has to build an elite roster comes when your star player is still on his first big contract, which typically counts as 25 per cent of the salary cap. Barnes is in the second year of his five-year deal worth about $224 million and is locked in at about 25 per cent of the cap over its term for three more years after this one.
Frittering away those years without giving him the proper support would be bad business, bordering on malpractice. With his jump to all-defence status last season and the leap he took in the playoffs suggesting all-NBA honours could be next, the time to pair Barnes with a co-star had arrived, something Webster broadly hinted at following the seven-game playoff loss to the Cleveland Cavaliers.
But how, and who?
According to multiple sources, the Raptors had conversations with Boston about acquiring Jaylen Brown, an all-NBA player at age 29 who was ultimately traded to Philadelphia. But when Leonard became available and the former Clippers star signalled he was interested in a reunion, he became their focus.
If it’s not an all-in move, it’s close, given the Raptors surrendered — among other assets — two future unprotected first-round picks and signed Leonard to a two-year contract extension worth $115 million, bringing the team's total obligation to $165 million over three years.
The Raptors' competitive timeline took a leap, and Barnes is here for it:
“(He’s) pretty good,” said Barnes about his new teammate, his understatement undone by a big smile Tuesday as he held court after the Raptors' final practice before hosting the Chicago Bulls for their season opener on Wednesday night (Sportsnet, Sportsnet ONE, Sportsnet+, 7:30 p.m. ET / 4:30 p.m. PT) at Scotiabank Arena.
But getting more serious, Barnes said: “We have the highest level of expectations. We want to win the championship here and that’s our expectation every time we step on the floor, but this is about how we can build on that throughout every game. You just can’t get there overnight. You've got to go through the season and focus on these games first in order to get to the playoffs and get to a championship.”
But is the rest of the roster ready?
The Raptors have no choice but to hope it is.
If time were more fluid, you could imagine a scenario where you could freeze-frame last season’s version of Leonard — 27.9 points and 1.9 steals per game with a true shooting percentage of 62.9 — with what the Raptors are hoping will be a career-best year from Barnes. Add in another year of development from the likes of Ja’Kobe Walter, Collin Murray-Boyles and Jamal Shead, and it’s easy to see the Raptors reaching the NBA Finals for just the second time in franchise history if everything comes together.
That was the thinking in giving Leonard a multi-year extension, no small thing given he is on the wrong side of 35 and has missed 44 per cent of his team’s games over the past nine seasons with a range of leg injuries.
Unlike his last tour through Toronto, the plan is that Leonard sticks around for a while, giving the Raptors a three-year window to win a second title during what should be Barnes’ absolute prime.
It’s not like getting superstar-level play from athletes in their late 30s is unprecedented. LeBron James has a moving van’s worth of career accomplishments at this stage, but of all his seemingly untouchable milestones, earning all-NBA honours for six straight seasons from his age-35 season on — a streak that ended last year when he was merely an all-star at age 41 — is a feat that may never be repeated.
But others have shown that the best-before dates for elite talent can extend far beyond the norm. Kevin Durant has rattled off two all-NBA seasons and an all-star-worthy campaign at ages 35, 36 and 37. Steph Curry was an all-NBA player at ages 35 and 36. Over the years, Kareem Abdul-Jabbar, Karl Malone, Tim Duncan and Chris Paul each made multiple all-NBA teams at age 35 or older.
The Raptors have no choice but to hope Leonard will follow suit, given that his deal will count for 30.5 per cent of the cap this season and 32.5 per cent next year and the year after that. Lucrative long-term deals for Immanuel Quickley and Jakob Poeltl make the margin for error even slimmer.
Complicating things is an Eastern Conference that has essentially been in an arms race since last season, with almost every relevant team making moves that can reasonably be expected to make them better — on paper — than a year ago.
Consider:
• The Detroit Pistons, a 60-win team and the No. 1 seed last season, are powered by three all-league-level players 25 or younger and have surrounded MVP candidate Cade Cunningham with six different players that have shot 40 per cent from three in recent seasons.
• The Boston Celtics have traded Brown, but will offset that with a full season of Jayson Tatum, and have added Paul George — still an elite shooter and, when healthy, one of the NBA’s best two-way players — and Mitchell Robinson, one of the NBA’s best rebounders.
• The Cavaliers, forever missing athleticism at the wing spot, have added Peyton Watson, a 24-year-old, six-foot-seven wing who shot 41 per cent from three for Denver last season, to round out their starting lineup better than ever before. Remember, this team has averaged 54 wins for the past four seasons.
• The New York Knicks may have lost Robinson to Boston in free agency, but given they went 16-3 in the playoffs with a net rating of 15.5 — which would represent an NBA record against regular-season competition — the reigning champs should be OK.
Those are the four teams the Raptors are trying to catch, based on last season’s standings.
The Raptors' 46-36 record was good for fifth, but among the teams that finished within three games of them in the standings, the Atlanta Hawks (46 wins) added Lu Dort and Aaron Wiggins and their championship experience from the Oklahoma City Thunder; the Philadelphia 76ers (45 wins) added Brown and James, along with crucial depth pieces; and the Miami Heat acquired two-time MVP Giannis Antetokounmpo.
Further down the ladder, the Indiana Pacers — just one season removed from Game 7 of the 2025 NBA Finals — have added one of the NBA’s best centres in Ivica Zubac while getting former all-NBA point guard Tyrese Haliburton back after missing all of 2025-26 with a torn Achilles.
Whatever the Raptors do accomplish this season, it won’t be easy.
“I love the pressure,” said Darko Rajakovic, who in his fourth season as an NBA head coach will finally be tasked with leading a team where the expectation is to win, as opposed to go through a rebuild. “That’s the whole point of professional sports. You want to compete … you want to test yourself against the best in the world …”
That’s what the Raptors signed themselves up for when they traded for Leonard in an effort to leverage what should be the best years of Barnes' career.
For the first time in a long time in Toronto, it’s winning time.
