Their franchise mythology was baptised in it, if you want to look at it that way. The Raptors were just two years removed from a 16-66 disaster in 1997-98 when Vince Carter lifted Toronto to a 45-win season — the first winning season the Raptors had known to that point — and a playoff date vs. the New York Knicks in 1999-2000. They lost in three games (first-round series were best-of-five at that point) but with Carter emerging as a superstar and rookie Tracy McGrady looking like he had the potential to follow, the afterglow outshone the disappointment.
Seven years later, it was Chris Bosh with help from TJ Ford, Jose Calderon and — yes — Andrea Bargnani who helped the Raptors jump from 27 wins in 2005-06 to a team-record tying 47 wins in 2006-07. A competitive six-game loss to the New Jersey Nets, led by Carter and Jason Kidd, gave hope that something sustainable was building in Toronto.
Seven years after was perhaps the most surprising turnaround of all, as a team that was slated to be disassembled with an eye toward rebuilding through the draft somehow found their feet just as surplus parts were being identified and went on to win a (then) team record 48 games, fueled by Kyle Lowry, DeMar DeRozan and … Greivis Vasquez.
Then there was the team that went 48-34 in 2021-22, which is a little bit of an outlier in that the core of the club had helped win a championship in 2018-19 and posted the best winning percentage in franchise history in the pandemic-shortened 2019-20 season a year later. The season the team spent in Tampa in 2020-21 and tanked their way to the No. 4 pick in the 2021 NBA Draft — the Scottie Barnes pick — was, at the time, considered an exception. The bounce-back performance in 2021-22 sparked in part by Barnes’ rookie-of-the-year production, welcome as it was, seemed more like a return to form rather than an out-of-nowhere mini-miracle.
Still, individually and collectively, they represent some of the most enjoyable seasons in franchise history. In each case, teams blew past expectations and pulled the franchise out of the bleakness that preceded them.
The 2025-26 Raptors improved from 25 wins two years ago and 30 last year to win 46 games — the first winning record in four years — and find themselves in the playoffs again. Their first-round series against the Cleveland Cavaliers starts Saturday afternoon.
It’s easy to nitpick how they got here (bludgeoning the NBA’s tanking class made up for their struggles against the league’s upper tier), but standing upright and in possession of the No. 5 seed in the Eastern Conference after the 82-game marathon that is the NBA’s regular season deserves to be celebrated.
“We knew that the defence was going to be there, we were going to just [be] super physical. Just having talks with the coaches, the organization about what we wanted to do, we felt like we could compete [this year],” said Barnes, the one player more responsible than any other for the Raptors’ rise this year. “We all knew that in training camp, when we came together and talked with each other. That was our goal and it’s great that we went out there and did it.”
And as for being tagged as significant underdogs?
“We’re going to do our job, we’re going to be who we are on the floor,” Barnes added. “That s— don’t matter.
But what we’ll learn over the coming years, and maybe as soon as next week, is whether the roster Raptors general manager Bobby Webster and head coach Darko Rajakovic have fashioned out of the incomplete set of tools left over from their old boss Masai Ujiri is safe for long, fast highway drives, or if the engine light that blinks occasionally deserves more urgent attention.
The sobering glance through franchise history — which isn’t all that different from the intermittent successes of most franchises not in San Antonio, to be fair — is that the hard part isn’t getting a team to the playoffs, it’s getting them there again.
Not to jump ahead of ourselves.
The focus in the third week of April quite rightly should be on whether this version of the Raptors can extend their season into the first week of May. The oddsmakers quite rightly say they can’t, properly dismissing the Raptors’ 3-0 record against Cleveland over a 25-day stretch from Oct. 31 to Nov. 24th when the Cavs were variously injured, disinterested and without James Harden — the 36-year-old star they acquired at the trade deadline in a win-now move that could blow up spectacularly, but more likely helps Cleveland get to the second round in five or six games, and maybe as far as the Eastern Conference Finals.
This collection of Raptors sees themselves as at least the Cavaliers’ equals but there is no debate about which team is under more pressure.
The Cavaliers felt they needed Harden to get them to the NBA Finals — likely their bar for calling this season an unequivocal success given they’ve been aimed at a championship for at least three years now and have yet to advance past the second round. Relying on Harden to make the difference is a choice, given he’s never made the Finals himself, and has a trail of spectacular playoff failures as the only black marks on an otherwise unimpeachable Hall-of-Fame resume.
But that’s their problem.
As much as this return to competitive relevance (barely, given that most NBA prognosticators give the Raptors no chance to advance against Cleveland, and by starting the series early on Saturday afternoon, the NBA itself is signalling no one outside of Toronto and Cleveland is all that interested in finding out for sure) should be enjoyed, whether it’s protein or mostly carbs is still TBD. Are the Raptors at the start of something meaningful that they’ll look back on with pride? Or is this the basketball equivalent of a week at a three-star all-inclusive — fun in the moment but not as much when the memories pop up a year later and the choices made are viewed with sober distance.
History says enjoy it while it lasts. A student of Raptors history knows that most of those surprise seasons ended in disappointment, the fun fleeting.
In a different circumstance, Carter and McGrady should have been the foundation of a decade of championship aspirations, but it flamed out quickly, leaving the Raptors to sort through soggy embers for decades, a never-ending debate about whether it was arson or faulty wiring.
Bosh? He recognized sooner than most that a team with him as the centrepiece wasn’t likely built for long-term success. Two first-round playoff exits were enough for him to head to Miami and a comfortable role as the third Amigo with LeBron James and Dwyane Wade. Four NBA Finals appearances, two rings and a Hall-of-Fame induction suggest he made the right decision.
The exception was the 2013-14 Raptors, and no one — not even Ujiri, who tried to trade Lowry before his run as the Greatest Raptor of All Time had even started — saw that coming, even after they pushed the veteran Brooklyn Nets to seven games in the first round. Lowry and DeRozan, it turned out, were future Hall-of-Famers and the Raptors were a year away from embarking on a three-year run of talent acquisition that is likely among the best in league history, as they drafted Delon Wright (20th, 2015), Norman Powell (46th, 2015), Jakob Poeltl (ninth, 2016), Pascal Siakam (27th, 2016), and OG Anunoby (23rd, 2017) while picking, on average, 25th. They also added Fred VanVleet as an undrafted rookie free agent in the summer of 2016.
All of that translated — in a roundabout way — into seven consecutive playoff appearances, nine series victories and the 2019 NBA championship.
The three-star all-inclusive became an annual trip to a luxury resort in the Caribbean featuring Michelin-calibre chefs, wellness coordinators and a wine cellar without price tags.
None of it was predictable back in 2013, but it made for the most compelling and enjoyable stretch in Raptors history.
Thirteen years later, the current edition of the Raptors has their bags packed for Cleveland.
Win or lose, where this latest surprise playoff journey leads is impossible to know for now, but you have to start somewhere.