The Toronto Raptors have arrived at their fork in the road, though it hasn’t come suddenly.
But they have a choice to make by 3:00 p.m. ET on Thursday, the NBA’s trade deadline. It’s unavoidable.
They’ve been moving steadily toward it ever since Kawhi Leonard opted to head to the Los Angeles Clippers in free agency in the post-championship summer of 2019 and Danny Green signed with the Los Angeles Lakers. The pace accelerated when the Raptors wouldn’t give either Serge Ibaka or Marc Gasol a second year on their deals this past off-season, in part so Toronto could keep their powder dry in the summer of 2021 to take a run at Giannis Antetokounmpo.
Ibaka and Gasol signed with the Clippers and Lakers, respectively, leaving the Raptors undermanned at centre and with nothing gained when Antetokounmpo opted to sign his lucrative extension with the Milwaukee Bucks before the season, taking him off the free agency market and scuttling years of careful planning by Toronto (among other teams) to put themselves in position to sign a two-time MVP as franchise centrepiece before he turned 27.
In that context, their current predicament – a 17-26 record and a nine-game losing streak – is only noise. Nothing they do before Thursday or after will be driven by an uncharacteristic slump driven by injuries, luck and dislocation. They remain confident that when healthy the team they can put on the floor even now is more like a top-four club in the Eastern Conference, rather than the bottom four they’ve been scraping along in for weeks now. They believe that if it were not for COVID-19 they would have been Eastern Conference finalists, and quite likely NBA finalists, a year ago and they’d be comfortably among the top four in the East again this year.
So now that they’re in 11th place and 2.5 games out of the play-in tournament, that won’t inform any decision they make on their future.
But teams in 11th place with two pending free agents in Kyle Lowry and Norm Powell are inevitably going to be looked upon by the rest of the league as potential sellers and the Raptors have been in the centre of trade speculation for weeks now.
The best intel I can offer is that anything is possible. The Raptors want to get better and will make choices driven by what steps they can take to enhance what they deem as their existing core in Pascal Siakam, Fred VanVleet and OG Anunoby, though rookie Malachi Flynn and late bloomer Chris Boucher are part of the equation. And there are those in the organization that still see considerable untapped potential in Terence Davis, whose second year has been less than ideal, on and off the court.
But that doesn’t mean they are desperate to get any kind of return for Lowry and Powell.
VanVleet just turned 27 and Siakam turns 27 next month; Boucher is 28; Anunoby, 23, is just entering his early prime. The Raptors aren’t looking to start from scratch. Far from it.
There is a universe in which the Raptors re-sign both Powell (who turns 28 in May) and Lowry (35 on Thursday) and go hunting for an impactful big who can fill the glaring void left by the departures of Ibaka and Gasol.
Building on what they have with players who have been with the organization and that love Toronto is hardly the worst option. And while re-upping with Lowry and Powell – along with $78 million on the books for VanVleet, Siakam, Anunoby, Flynn and Boucher – could easily push the Raptors near the luxury tax threshold when the rest of the roster is filled out. Money is not considered to be an issue, say insiders.
Starting from that point and figuring out how to improve while getting another couple of quality years from Lowry and Powell is a surer path to contending in the East than breaking the enterprise up and selling for parts of uncertain value.
And if there’s course correction required at some point after that? Lowry’s value isn’t going to fall off a cliff and Powell – presuming he continues shooting at the elite level he has the past two seasons – will always be movable and might be easier to trade while under contract without the uncertainty of free agency clouding the picture.
So not trading Lowry or Powell, or both, on Thursday isn’t out of the realm of possibility and might even be desirable, depending on what happens as the market firms up.
The key message here: the Raptors know they’re on a losing streak, they just aren’t making any decisions based off it.
All that said, Toronto hasn’t closed any doors.
As the losses have mounted, the usual suspects have circled back on Lowry with the likely destinations remaining the Philadelphia 76ers and the Miami Heat, who each view him as someone who could help them get over the top in a highly competitive Eastern Conference.
The Raptors haven’t been shopping him, but they’ve been listening. They had a management meeting Monday night to share intel internally. Opinions are forming. Similarly, Lowry hasn’t been pushing for a trade, but understands that getting moved could offer him not only a chance to win another title – cementing his legacy and likely solidifying his case as a Hall of Famer – but since his Bird rights would travel with him, allow his new team to sign him even while over the salary cap. That detail would give him the best chance to sign a contract somewhere in the ballpark of the $30 million annually he’s earning now. If he stays in Toronto and decides to leave in free agency, he would be relying on teams that have cap space to set the market, a much less certain proposition.
In that scenario, the Raptors could end up as the best option, just as they were in 2017 when Lowry explored free agency only to see the market shrink quickly. He was fortunate that the Raptors were waiting with a three-year deal for $100 million that far outstripped anything that was otherwise available to him, although easily proved good value on that deal.
But finding a fit is tougher than most might think. The Sixers have the requisite expiring contracts to flesh out a deal, and more draft capital than the Heat, but are light on difference-making prospects that complement the Raptors' existing core. Tyrese Maxey is intriguing, but the Raptors have VanVleet and Flynn at the same position. Does adding a 20-year-old point guard and a future late first-round draft pick make the Raptors better? Is it fair return for Lowry, who may still be Toronto’s best player, saying nothing of his iconic status? Does the Sixers' Matisse Thybulle (4.3 points per game career average over two seasons) really move any needles?
I can see why Philly would be in a rush to make that trade, I’m not sure why Toronto would.
The Heat have different challenges. As things stand, Miami won’t have a first-round pick they can trade until 2028 as all they've all been dealt or are tied up with pick protections. Teams aren’t allowed to trade picks in consecutive years and not further out than seven seasons. In theory, Miami could acquire a pick from another team, but that would mean dipping into their pool of prospects that a team like the Raptors might be interested in.
The fit with Miami includes Lowry’s willingness to sign there and the possibility of acquiring some collection of the Heat’s younger core. Certainly, adding 21-year-old Tyler Herro, who played well as a rookie in the playoffs last season, would pique the Raptors' interest, as would pending restricted free agent Duncan Robinson. The soon-to-be 27-year-old is one of the best shooters in the league and would fit well alongside the Raptors' core. And given Toronto’s lack of bigs, rookie centre Precious Achiuwa would be a nice piece, too.
But all those players are on rookie deals that hardly make a dent in the roughly $25 million Miami would have to send out to match Lowry’s incoming salary, and they are each part of the Heat’s existing rotation. To make the money work, the Heat would likely need to include pending free agent Kelly Olynyk ($12.6 million), who is starting for them, and one of either Goran Dragic ($18 million), who is their leading bench scorer and a fixture in closing lineups, or Andre Iguodala ($15 million), who is still a prominent part of their rotation and remains an elite defender with a bottomless well of smarts and experience.
When the Heat traded Meyers Leonard and his $10-million expiring contract to the Oklahoma City Thunder for Trevor Ariza, a Lowry deal got a little harder.
Might Lowry be traded before Thursday at 3 p.m.? He might be, if the deal is right, but even as their season spirals, there is good reason why the Raptors don’t view themselves as motivated sellers. They will deal only on their terms.
Still, of the two, Powell may be more likely to be traded, and league sources suggest the Raptors have been more aggressive in soliciting offers for Powell, who will almost certainly opt out of the last year of his deal, looking for a big raise from the $11.6 million he would otherwise make.
He’s proven himself one of the NBA’s best shooters and has a slashing element that most of the league’s elite marksmen don’t have.
But what is his trade value?
His contract status complicates things – teams that view him as a starter might want to surrender less because they might have to pay Powell something in the range of $72 million – the expectation being that the Brooklyn Nets' Joe Harris might provide a benchmark for the Raptors wing. Teams that view him as a rotation piece for a playoff push might want to surrender less because Powell might be less likely to sign going forward in that role.
“He’s been really good and shoots it a high clip. I just don’t know if he’s a starter in the NBA,” said one Eastern Conference executive. “And when you’re putting up those kinds of numbers and he gets to free agency, you have to pay him, so maybe that’s why they’re looking at capitalizing on him right now because his value is what it is.”
Would Powell be enough to pry a starter-level big and maybe a future second-round pick?
Could he provide the means to get the Raptors in on deals for John Collins in Atlanta – a pending restricted free agent – or Richaun Holmes, a pending free agent big in Sacramento with chops as a rebounder and rim protector, two of Toronto's most glaring weaknesses?
The Raptors are going to work the Powell angle hard, is my guess, and I think it’s more likely he gets moved than he doesn’t.
I’m less sure about Lowry for the reasons I’ve been saying all along: He’s not pushing to go and the obstacles to a proper return for a player of his stature remain significant.
Whatever path they take brings no guarantee. But the Raptors could look considerably different over the next 24 hours.
If they do, chances are the changes are just beginning.