It was mid-September, a rare slow moment in the NBA calendar, but Charania was keeping tabs on a pair of extended dramas involving two star players, Damian Lillard and James Harden, who were both demanding to be traded by their respective teams. “If I take a day off, never mind a week off, I put myself behind the eight ball,” Charania said. At the restaurant, he wore all black — suede jacket with a hood, sweatshirt, skinny pants — and a pair of John Geiger sneakers that were white save for what appeared to be a coffee stain. Charania drinks only two cups a day but exudes caffeination; his legs shook constantly under the table, and I lost track of how often he reached for his phone, which had 125 unheard voice-mails, 72,443 unread emails, and an unceasing stream of texts, many of which he responded to as they came in. He averages 18 hours of screen time a day and was proud of how far that number had dipped on a recent vacation to Portugal with his family, even if he had continued tweeting minor news — “Skal Labissiere has agreed to a partially guaranteed one-year deal with the Sacramento Kings” — throughout the weeklong trip. “I prefer the poolside sit-and-do-nothing vacation, so I can still be on my phone as constant as I wanna be,” Charania said. “But did it get to, like, 14 hours? Yes. Did it get to, like, 12 or 13 hours some days? Yes. I think that’s a win.”
Charania, who is 29 and has been a working NBA journalist since he was a teenager, is an omnipresent figure in the lives of everyone in the league. Earlier this year, Steve Kerr, the head coach of the Golden State Warriors, was so miffed that Charania had leaked a tactical change the Warriors planned to make that he suggested Charania had a mole in the locker room. Kevin Durant once said on his podcast that it seemed like Charania was in the CIA. “Shams a creep, yo,” Durant said of Charania’s ability to gather intelligence. When there is big NBA news to be broken, the only question anyone has is whether they will learn about it from Shams or Woj.
Woj is Adrian Wojnarowski, ESPN’s own senior NBA insider and Charania’s onetime mentor. Wojnarowski gave Charania his first big job in journalism and helped train him in the murky reportorial art of becoming an “insider” — among the best-paying and most intrigue-filled jobs in journalism — only to have Charania become his chief rival in the race for NBA scoops. “These two guys who never even played varsity basketball dominate information flow in the NBA with a direct line to the commissioner, to agents, to owners, to everybody, because of platforms they’ve created basically out of thin air,” one longtime NBA front-office executive told me. Charania and Wojnarowski have become celebrities in their own right — Wojnarowski has more than 6 million X followers — by serving as vessels for the daily stream of news that holds NBA fans’ attention even (and perhaps especially) when there aren’t any games being played.
28. Toronto Raptors (Last Year 23)
What a fall for a team that steps into the unknown with a first-year head coach (Darko Rajakovic) and its steady-hand point guard — Fred VanVleet — gone to the Houston Rockets. It is hard for a franchise that gives Jack Armstrong a live microphone and lets him sing and screech and talk about beer to rank this low.
Rajakovic promises a livelier offense, and boy would that be a relief after watching Pascal Siakam, Scottie Barnes and O.G. Anunoby take turns dribbling to nowhere.
Under Nick Nurse, Toronto compensated for a miserable half-court offense by winning the possession game — swarming the offense glass, snaring turnovers, sprinting to fast-break buckets. It was tactically interesting. Will Rajakovic scrap it? With Jakob Poeltl back, the Raptors might play a more conservative defense.
Gary Trent Jr. is an old-school gunner. Jalen McDaniels is always just on the verge of being a reliable 3-and-D guy; is this the year? I’m betting on a bounce back for the ultra-switchy Precious Achiuwa. Every Chris Boucher dribble and catapult 3 pulses with danger.
This is a massive Year 3 for Barnes, who was rendered off limits in trade talks for Kevin Durant and Damian Lillard, per league sources.
The new court is a home run:
The giant claw mark is perfect — the way it looms as a shadow on the floor and then pierces the boundaries in black. It really does look like a dinosaur stomped on the court.
What are the Raptors’ options with Dowtin?
The contract situation has Dowtin playing from underneath in camp.
Technically, the Raptors have enough space under the NBA’s luxury tax that they could keep Dowtin and waive one of the players with a fully guaranteed contract. The Raptors would still owe that player his money, but they could still keep Dowtin without nudging into the tax.
(The luxury tax line is usually treated like a hard cap if you are close to it. Below-tax teams receive a distribution of the tax payments made by every other team, so a contract that pushes you just past the tax line could end up costing you significantly more money. So, while the Raptors don’t need to stay below the tax, going over the luxury tax amount would have cost them over $15 million in payouts last year.)
So, yes, the Raptors can waive or try to trade a player in order to keep Dowtin. They are allowed and have the space to do so. It becomes a question of whether Dowtin can make enough of a case in a small pre-season window to force the Raptors’ hand.
If the Raptors instead cut Dowtin, it’s likely his next stop will be elsewhere. Because of how G League player rights work, Dowtin couldn’t go directly to Raptors 905. His G League rights were acquired by Delaware (the Philadelphia 76ers’ affiliate) this off-season. A player’s G League rights don’t matter if he’s on an NBA or two-way contract — that’s why Dowtin could play for the 905 last year despite the Lakeland Magic holding his rights — but once a player is a free agent, he has to return to the team that holds his rights if he re-enters the G League. It’s a bit complicated, but the short version is that a G League stint for Dowtin would come in Philly’s organization.
It’s also possible Dowtin would be claimed or signed to a two-way contract before he even makes it to the G League. There are 16 open NBA roster spots right now, which are open either due to camp competitions for them or as teams try to lessen their luxury tax bills by using a shorter roster. There are also nine open two-way contracts around the league, and there is usually some churn in those spots right before the season.
Could the Raptors change up their two-way spots?
There is one other path for Dowtin, though he may not be amenable to it: The Raptors could waive Dowtin and one of their two-way players, then re-sign Dowtin to a two-way deal.
This is possible because Dowtin’s contract has no guaranteed money, whereas, say, a $100,000 camp guarantee would have left him ineligible to sign a two-way later.
There are some complications with this route. The primary concern is that Dowtin would have to clear waivers, which is no sure thing. The Raptors would also lose what would have been Early Bird rights on Dowtin for next off-season, though those matter a bit less for end-of-roster players. You would also lose one of your current two-way players, none of whom you hold the G League rights for. (Ron Harper Jr. and Markquis Nowell would have to enter the G League Draft, while Javon Freeman-Liberty’s rights are held by the Windy City Bulls.)
In this scenario, Dowtin would go from a $900,000 guarantee on opening night to a $560,000 total salary for the year as a two-way, only half of which can be guaranteed. Given Dowtin’s service time, he would stand to make $114,000 if he got a 10-day contract at any point. Would Dowtin be open to another year on a two-way contract, waiting to be converted to a standard deal after the trade deadline? Or would he prefer to take his chances in the G League as the No. 1 point guard available if an NBA team needed a call-up? It’s a tough decision.
Other Raptors camp contract implications
The ability to waive a two-way player and fill that spot with someone else is relevant for Mo Gueye and Makur Maker, too.
Those players are in camp on Exhibit 10 contracts, which give the Raptors the right to convert them to a two-way contract, if they decided that they liked one of those players better for a two-way spot than the three players they have under two-way contracts. There will also be a number of Exhibit 10 and two-way types on the waiver wire later this week, and the Raptors have gone that route in the past to fill a two-way spot.
Even if the Raptors liked Gueye or Maker, it might not be pragmatic to switch them into a two-way spot. This is where G League rights come up again. The 905 hold the G League rights to Gueye and Maker, having acquired them in trade this off-season. Even once cut, those players are 905-bound, and because they’re on Exhibit 10 contracts, they’ll receive a $75,000 bonus if they stay in the G League long enough. Those players are already locked into your system, whereas Harper, Nowell and Freeman-Liberty, if cut, would revert to the draft or their prior team.
All of that is to say, with how things are currently structured, the 905 would have Gueye, Maker, Harper, Nowell and Freeman-Liberty (plus Kevin Obanor and Darry Morsell, who signed Exhibit 10 contracts and were waived earlier in the summer). If you made a change in one of the two-way spots, you’d risk losing one of those players from your system. There’s no strong incentive to convert Gueye or Marker (or anyone else from the 905) to a two-way unless there is a threat of another NBA team signing them. Usually, in those cases, an agent would give the Raptors a heads up and the opportunity to sign them first (similar to what happened with Paul Watson Jr. in 2020).
The Raptors also have two Exhibit 10 contracts remaining. I mention this because it’s possible that you’ll see Gueye and Maker waived, then two new players signed and waived later this week. We’ll break down those 905 implications when they happen, but for now, just know those would be 905-oriented moves.
While former head coach Nick Nurse ran hot and cold on Trent’s defence, which, to be fair to Nurse, ran hot and cold, the Raptors as an organization have adored Trent’s personality since he arrived midway through the 2020-21 season. Even if Trent’s playing style hues most closely to that of a sixth-man scoring guard, not the most valuable player type out there, his work ethic and confidence have endeared him to the franchise.
When Nurse asked him to become a turnover hound defensively, Trent immediately became among the leaders in deflections. He is still exploitable in one-on-one situations, but he has worked diligently to improve. Rajaković said he wants to make Trent’s defensive approach a bit “more disciplined” this year, which is in line with his philosophies for the whole team.
The bigger shift will come offensively, where Trent previously had the green light to do his thing, for the most part. If he is dribbling multiple times to create space for himself to get off a jumper, something has gone wrong, either on account of his failure or his teammates’.
Trent seems entirely unbothered.
“I would say really it’s just whatever comes (from) the system,” Trent said of the shots he may now take versus the ones he took over the last few years. “Obviously it’s a lot of 3s, a lot of spacing, a lot of point-five second basketball — almost close to the Spurs with (their) “Summertime” offence and kind of close to the Warriors in a sense, which is stuff we are trying to practise.”
To be clear, Trent will still be expected to score a lot for this team. As is the case with Siakam, the hope is that the process changes enough to make them both more efficient and more unpredictable as offensive players. Heading into his free-agent year, it is likely that Trent is going to have to do that coming off the bench.
For Trent Jr., the change seems to have been a long time coming. Ever since he arrived in Toronto, it seemed like his best fit would be as a quick trigger scoring option in the second unit. But given the Raptors’ lack of shooting up and down their roster, the 24-year-old has started 83 per cent of the games he’s been available for since joining Toronto at the trade deadline during the 2020-21 season. It kept more shooting in the starting lineup but meant the Raptors backcourt was on the small side when Trent Jr. played alongside since departed Fred VanVleet, and it also meant another mouth to feed in a starting five that where everyone seemed hungry.
It looks like that will be changing under Rajakovic, who has started incoming point guard Dennis Schroder ahead of Trent Jr. in Toronto’s two exhibition games. It hasn’t been formalized – the head coach says he’s going to wait until Toronto wraps up its preseason schedule with a game in Chicago on Tuesday night and at home against Washington on Friday – but Trent Jr. seems to know what’s up.
“As of right now, it’s going to be what it’s going to be,” he said after practice on Monday. “I haven’t heard anything about coming off the bench [or] starting. Obviously, the first two games I’ve been coming off the bench. Practices, I’ve been with the second unit in everything we’re doing, [so] the writing is on the wall. So we’ll just continue to go, come in and help to win as much as I can.”
Trent proved himself pretty adaptable last season when Nurse did tinker with his role at times.
He averaged 19.6 points per 36 minutes in the 22 games he came off the bench last season compared with 19.5/36 in his 45 games as a starter, but he was more efficient coming off the bench, with a True Shooting percentage of 58.0 compared with a 55.2 mark while starting.
Getting Trent to embrace his new role will be one of Rajakovic’s first tests as a head coach.
Trent Jr. is a pending free agent, and – presuming he doesn’t get some version of the four-year, $113-million extension he’s eligible for in the coming days – would hit the open market next summer after opting into the final year of the three-year $54 million contract he signed prior to the 2021-22 season this year.
Taking a step back in term of responsibilities or minutes is not normally well received by players heading to free agency.
Trent Jr. praised the open lines of communication Rajakovic has established early in his Raptors tenure but said that to this point he hasn’t discussed his role – or apparent change in role – with Rajakovic and isn’t the type to go asking.
“Obviously you work to start in the league and start for a team and help the team as much as you can,” said Trent Jr. “But again, I have no control over that. So whatever it’s going to be, it’s going to be. I can only control me coming in, working, being a great teammate and contribute to winning. That’s all I can help with. That’s all I can do. There’s no time to complain, nag about what’s going on or how my situation is not what I wanted. There’s none of that. I’m coming here to work. And I’m going to do what I need to do to help this team win.”
Rajakovic said he’s not worried about having any hard conversations with Trent about his role on the team if, or when, that time comes.
“You can look at Hall of Famers, some of those guys were coming off the bench and being amazing players at different parts of the season,” said Rajakovic. “You’ve just got to be ready to go out there and be (a) pro.
“Everything I’ve seen so far from Gary is he’s that guy. He’s a pro.”
The 24-year-old Trent exercised his US$18.56 million player option on June 20 to return to Toronto for this coming season.
Rajakovic, who became the Raptors 10th head coach just seven days before Trent exercised his option, said he would not make any decisions based off of anyone’s contract situation.
“I’m not looking at who’s under contract or not,” he said. “I’m getting ready for a practice, getting ready for film. We have people who are paid to do that job.”
The Raptors continue their pre-season in Chicago on Tuesday. Trent said he and his teammates are looking forward to a stiffer test than what they faced in a 134-93 victory over Australia’s Cairns Taipans on Sunday.
“Our main focus going into Chicago is just us,” said Trent. “Our game last night we just wanted to make sure we were solid on both ends, offence and defence, and obviously that wasn’t an NBA team, but they were still a good team.
“Now we are going to Chicago and it should be a good road test for the pre-season and get us acclimated for the first game on the 25th.”
It was only a few months before he was hired onto the Toronto Raptors coaching staff that Wade was at Scotiabank Arena coaching another big game. When the WNBA held their first game in Canada on May 13th, it was Wade’s Chicago Sky that won over the Minnesota Lynx in front of a packed, 19,000 strong crowd at Scotiabank. After the game Coach Wade, then head coach and general manager for the Sky, jokingly claimed SBA was “his house,” being the first coach to ever win a WNBA game there.
“You remember that?” Wade laughed, when asked if it was nice to be “home” now, “Yeah, I claimed it” he laughs. He said that while he definitely did not expect to be in this position (as a Raptors assistant) while in Canada for the game, the energy Toronto brought that weekend helped influence his decision to accept the job a little.
“I can definitely see WNBA in the future here,” he added about Toronto.
After the tough choice to leave the Chicago Sky in June, who Wade won a championship with in 2021, he’s now ramping up to begin his first season with the Raptors. Luckily, Coach isn’t the only new face around the Raptors this season — along with him, Rajakovic, and most of the coaching staff, there are also quite a few new players.
“I think it gives us a new energy, that’s always exciting. I think that’s always good for players, when they have that new energy,” Wade said, noting the benefits to having so many new faces around. Yet, having to bring so many people up to speed so quickly can also have it’s challenges.
“You know, everybody wants it to work right away, so it’s process. You just have to have a little bit of patience.” He also went on to say that now is the time for trial and error, and for learning — which surely the Raptors have had time for. They’ve only had two preseason games as they head into their third week since training camp started on October 3rd. They’ll head to Wade’s old stomping grounds, Chicago, to play on Tuesday before coming back to Toronto to wrap up the preseason on Friday.
Wade also mentioned another easy thing in getting everyone up to speed on the Raptors’ new system has been the level of basketball IQ that the players, coaches and staff all have. Something that Darko Rajakovic mentioned on media day, when asked about what Wade will bring to the staff, was how much he prioritized international experience in his hiring. Wade himself, along with his experience coaching in the WNBA as a head coach and assistant coach, also worked overseas as a coach in Russia and France.
Any way you slice it, by season’s end, one coach is going to be right about the state of Toronto’s NBA team.
It’ll either be Nurse, who ran the NBA’s shortest bench over the past couple of seasons because he clearly believed there was nobody sitting down there who deserved a bigger opportunity, never mind upper management’s pleadings to the contrary.
Or it’ll be Rajakovic, who got the job after Nurse was fired in part by insisting there is talent lying dormant in Toronto that’s poised to blossom with the right encouragement. It’s a line of thinking that just happened to jibe with the off-season insistence of team president Masai Ujiri.
“I think there’s talent (on the bench). It just hasn’t come out yet,” Ujiri said after he fired Nurse in April. “We’re still developing, and this takes time sometimes. Maybe we could be wrong, but we still believe in those kids as talents.”
Maybe there’ll be no better example of those divergent outlooks than Malachi Flynn, who has languished on the pine alongside the allegedly untapped talents of Christian Koloko and Precious Achiuwa, among others. Drafted 29th overall by Toronto back in 2020, by last season Flynn played in just 53 games; he was left on the bench for the duration of the other 29 — 30 if you count the play-in loss to Chicago in which he was never asked to check in. And even when Flynn did get on the floor, he usually didn’t last long, averaging 13 minutes a game.
And yet, when Rajakovic was asked about Flynn after Monday’s practice at the OVO Athletic Centre, the new coach’s eyes bulged with excitement.
“Malachi,” said Rajakovic, “is somebody who I have a very high confidence in.”
The obvious followup question, glimpsing Flynn’s nondescript career stat line, would be: Um, why?
“I think he’s a player that he’s not even close to maxing out,” the new coach said. “I think there is so much room for growth in his game on the ball and off the ball. I think he’s really good off ball coming as a secondary guy, coming off wide pindowns or second side pick and rolls. I think he’s somebody who can break down the defence pretty well and touch the paint. And we’re just going to continue working on those skills with him, like finishing, finding the open man. Like (Sunday) night (in a pre-season win against Australia’s Cairns Taipans), he was wide open for a layup and he tried to make the extra pass. Just score. When nobody’s stopping you and you beat the defence, be aggressive to score.”
It’s the kind of glass-half-full assessment that might make a hardened observer wonder when did the NBA morphed into the G League? Like, if you’re in your fourth year in the NBA and you still don’t know when it’s time to lay it in, you might never get it.
Further in that vein, it’s not as though Flynn hasn’t had his chances. In 144 career games, he’s proven he isn’t afraid to shoot. But his career 34 per cent marksmanship from three-point range ranks below league average. Beyond that, he’s never solidified himself as a particularly savvy playmaker, and his defence was has never been adjudged dogged enough to permanently endear him to Nurse.
“This baseless lawsuit is a public relations stunt by the Knicks,” reads the preliminary statement of the filing. “It has no business wasting judicial resources given the all-encompassing arbitration clause in the parties’ governing agreement.
“Unless they reverse course and accept the jurisdiction of the NBA Commissioner as the parties agreed, the Knicks have chosen a forum that would likely not even be able to commence substantive proceedings until after the upcoming NBA season concludes and not ultimately resolve the dispute until 2025 at the earliest.”
Spokespeople for MLSE and the Raptors offered no comment on the new motion or the lawsuit itself.
The Knicks filed suit against the Raptors, Rajakovic and former Knicks scouting employee Ikechukwu Azotam on Aug. 22, alleging the defendants conspired to steal thousands of videos and other scouting secrets in July and August.
The Knicks are seeking unspecified damages and a ban on the further spread of their trade secrets.
They claim that their intellectual property — scouting and play frequency reports, a prep book and a link to valuable software — has been downloaded thousands of times by Raptors employees.
The lawsuit identified Azotam as the alleged mole. Since August 2021 Azotam had directed the planning, organizing and distribution of all video scouting responsibilities for the Knicks’ coaching staff.
The Knicks allege Rajakovic, hired as Toronto’s new head coach in June, player development coach Noah Lewis and 10 unidentified Raptors employees received proprietary information and sometimes directed Azotam to misuse his access to Knicks information.
The Raptors’ motion filed on Monday notes that, if the Knicks intention is to prevent the use of its intellectual property, then going through the NBA’s arbitration process would be faster and more effective.
Flynn said he spent the offseason trying to get bigger, a tough task for a player listed at 6-foot-1, 175 pounds. He’s added five to seven pounds of “good weight,” he said, trying to bulk up after realizing how tough it is to play in the NBA against grown men.
“Definitely not jumping out the gym, never will be, but feeling a little bit stronger on defense, taking bumps a little better and little more explosive so it feels good,” he said of the change.
The change has caught the attention of Rajaković who has liked what he’s seen from Flynn through the preseason so far. The fourth-year guard had five assists in his first showing of the preseason, despite just one field goal on six attempts, and then added 10 points off the bench against Cairns on Sunday
“Malachi is somebody who I have a very high confidence in,” Rajaković said. “I think he’s a player that he’s not even close to maxing out. I think there is so much room for growth in his game on the ball and off the ball. I think he’s really good off-ball coming as a secondary guy, coming off wide pindowns or second-side pick and rolls. I think he’s somebody who can break down the defense pretty well and touch the paint. And we’re just going to continue working on those skills with him, like finishing, finding the open man.”