Raptors have created precarious environment for players by delaying the inevitable

The Toronto Raptors are building from the middle. That much is clear. Rather than bottoming out and selling off veterans in hopes of increasing their lottery odds to be good down the line, the Raptors wish to remain competitive and keep their options open.

That could mean trading Pascal Siakam for the right package of young players and picks. Or it could mean trading young players and picks for a star like Kevin Durant or Damian Lillard, who they were in the running for as recently as last week. But one thing is for sure: something has to give.

“We understand that we're always going to put ourselves in the right place, to have opportunity when these things come along and I think… There’s a reason why our name is always mentioned when these things come along,” Raptors’ president of basketball operations, Masai Ujiri, said about Lillard during Monday’s media day press conference.

“And so with this opportunity, yes, we are aggressive, we put our best foot forward. It takes two to do a deal. And we believe in our city, we believe in this place. And we'll continue to attack those things when the right one comes — the right one will come. I think we've shown in the past that we could do that.”

During the same press conference, Ujiri noted the Raptors also considered going younger this offseason, presumably trading for a player like Scoot Henderson at the 2023 NBA Draft, or making a deal based around Siakam with the Atlanta Hawks. He said that “sometimes those opportunities are there and sometimes they’re not there. We can’t force them. It takes two to do deals and you move on when those deals are not there.”

That’s not a bad way to build a team, to be certain. Remaining patient, keeping the powder dry, developing players, and keeping the books flexible so you can make an opportunistic trade when the time comes is intuitive thinking, especially considering the parity of the NBA and how fast the league moves these days. One day you could be a bottom-feeder ready to take advantage of the draft like the Raptors did in 2020-21 by selecting Scottie Barnes No. 4 overall, and the next you could find yourself a superstar away from an NBA championship like the Raptors did in 2018, when they traded for Kawhi Leonard.

But there are diminishing returns from building from the middle, because the longer you do it, the harder it is to manage — especially when you consider the human element of what it means to actually play for an organization that lacks a clear direction, is constantly having trade discussions, and fails to provide players with a meaningful sense of security.

In the last calendar year alone, Siakam, O.G. Anunoby, Gary Trent Jr., and Gradey Dick’s names have all been reported to come up on the trade market to varying degrees — not to mention players who have been mentioned as salary ballast like Chris Boucher, Thad Young, and Otto Porter Jr.

That’s not something the Raptors can necessarily control, but it is something the players see. After all, NBA players read the news and are on social media, and that stuff can take a toll on a player when it happens year after year, trade deadline after trade deadline, affecting the way they play and the relationships they build in the organization.

Still, it’s one thing if it’s happening to role players, and another when it happens to the best and most important players on the team.

“I can't control what you guys do on social media... But I do have feelings for the players, and they are human, and everybody is,” Ujiri said about the trade speculation. “This is just the nature of how the NBA is, and the flux has become even more now with social media and player movement. It's one player tomorrow, another day our names will be brought up again.”

Ujiri clarified that Anunoby was never brought up in trade discussions for Lillard this offseason despite reporting to the contrary,

“So these are things we relate maybe to the player and we hope that at least we've seen that we can show them, or talk to them, or be honest with them when these things come around and have to be done,” he said. “The best way with all these players is always to be honest and direct with them. That's what we've always been here.”

In addition to trying to keep their players in the loop at all times, the Raptors can fall back on their history of treating their players right when it comes to the way they managed Kyle Lowry and Fred VanVleet at the 2021 and 2023 trade deadlines, refusing to trade them somewhere they didn’t want to go for a package that wouldn’t move the needle in a significant way. And they can fall back on their history of paying players when it comes to extensions and free agency, often giving them player options on the final year of their deals.

But as the Raptors get set to open the 2023-24 season, they have three core players on expiring contracts, with Siakam, Anunoby and Trent Jr. all extension-eligible and unsigned beyond this year. Ujiri confirmed the Raptors are yet to have contract discussions with any of the three aforementioned players, wishing to see how they fit into incoming head coach Darko Rajakovic’s new system first.

“Yeah, it is difficult to navigate,” Ujiri said about having three players on expiring deals. “We do believe in these players: that’s why we got them, that’s why we drafted these players, the players that you are talking about. I think as the year goes on we will figure out which way we’re going to go in terms of how they adjust to the new coach, new system and how we’re going to play.”

That makes sense for Anunoby, who is unlikely to sign the four-year, $116-million extension that he is currently eligible for. It also makes sense for Trent Jr., who is yet to prove himself flexible enough to adapt to any situation and play style, especially on the defensive end.

But when it comes to Siakam, a two-time All-NBA player and the longest-tenured Raptor who has proven adaptable enough to fit into any system and any role asked of him, playing the waiting game is a risky strategy when Siakam could follow in VanVleet’s footsteps and walk in free agency for nothing next offseason.

“We do believe in Pascal. We believe that a lot of our players didn’t play the right way last year and we want to see them play the right way,” Ujiri said about Siakam’s lack of long-term extension. “I said that we were selfish, I’m not running away from that. We were selfish and we did not play the right way. So, let us see it when we play the right way.”

Meanwhile, the three players all refused to comment on whether or not they would even sign a long-term deal if their maximum contract was offered by the Raptors this summer. But there was a palpable sense of frustration and anxiety in the air as media day unfolded — one uncommon for the start of what should be a new and exciting season as the Raptors get set to fly to Vancouver for training camp Monday evening.

“I’ve never been a selfish player in my life,” Siakam said. “I’ve always played the game the right way and that’s from the first time I started playing basketball. I’ve always been a team player. All the things that I do on the basketball court is about the team and I’ve been like that my whole career.”

When asked about his contract situation, Siakam said: “For me, I’m under contract, right? I’m a Raptors player. That’s literally what I’m focused on. I’m focused on the present and that’s all I can really care about right now.”

Siakam acknowledged that as a kid who grew up in Cameroon, he is living the dream right now. But sometimes the business of the NBA can take a toll on him, saying “I want to keep enjoying it. It gets so super sometimes stressful because of all things that are happening, but I’m actually living my dream.

“I always want to be the best I can be. At the end of the day, that’s what I focus on,” he added. “There are a lot of things I can’t control. I try to focus on the things I can control and the things I can control are me going out there every single day, being a great human being and working hard to be the best player I can be.

“So yeah, I’m focused on the basketball and being happy and being with people I care about. And that’s all I’m focused on.”

But if hearing his name in trade rumors and lacking the security of a long-term contract can weigh on someone as accomplished and mature as the 29-year-old Siakam, imagine how his significantly younger teammates are feeling. And imagine how that tension could affect a locker room without a clear vocal leader, especially considering the history of NBA players playing more for their stats than for their team in the final year of their contracts in order to maximize earnings.

“The most important thing for us is that we continue to grow our team and our players and build their confidence and make the environment where they play very conducive for them to succeed and to play better,” Ujiri said.

But by continuing to build from the middle and failing to pick a clear direction, the Raptors haven’t created an environment conducive to success.

Instead, the current environment is an extremely precarious one: With three of their best players entering the final years of their contracts, no clear hierarchy or leadership structure, and a lack of security for their most important players, the Raptors are not only in no man’s land — they are anxiously waiting for the next shoe to drop.