Messiness with Leonard, DeRozan leaves Ujiri searching for answers

Eric Smith and Michael Grange delve deep into comments made by Raptors president Masai Ujiri at his press conference, following the blockbuster DeMar DeRozan for Kawhi Leonard trade.

In normal times, it would be a day of celebration.

The Toronto Raptors were poised to confirm the acquisition of the most decorated player in their history, a 27-year-old superstar in his prime.

With the move, their future – perhaps for the first time – could reasonably include expectations of playoff dates in June.

Book those hotel rooms in San Francisco; the Raptors are coming.

But these aren’t normal times.

There were no new players anywhere in sight. There were no back-slapping jersey presentations. There were no beaming friends and family in the first row.

Masai Ujiri, who engineered the still jaw-dropping trade of Raptors quintessential star DeMar DeRozan for Kawhi Leonard — a player as impactful as any member of the NBA’s very small royal family you would care to name — wasn’t taking a victory lap in his first public comments on the deal.

He was at a podium alone. He was delivering a eulogy while trying to sound optimistic about the hereafter.

He was tap dancing over hot coals.

First, he had to address the messy perception — driven by DeRozan himself — that he had betrayed, lied to or at the very least misled the longest-serving and most accomplished player in Raptors history as a prelude to trading him after a career-best season and a franchise-record 59 wins.

Ujiri wasted no time, beginning his 20-minute address by apologizing to DeRozan if there was a “miscommunication” — the miscommunication being DeRozan believed he had been told he wasn’t going to be traded, while Ujiri believed he’d been professionally vague enough that his words couldn’t be interpreted that way.

“I had a conversation with DeMar at Summer League,” Ujiri said. “We spoke and I spoke to him. I think maybe my mistake was talking about what we expected going forward from him. Not necessarily talking about a trade but what I expect from him going forward and I think that’s where the gap was because, in my job, I always have to assume that I’m going forward with the team that I have.

“If there was a miscommunication there, I do apologize to DeMar and his family and his representation. It’s not what I meant,” Ujiri said. “These things come and go, opportunities come and go and we have to react, in my position, and I had to react at this time.”

On Instagram, DeRozan — said to be devastated by the deal — responded with a ‘hand slapped to forehead’ emoji.

Ujiri was – quite literally – sweating. It was admittedly stuffy in the Raptors old practice gym on the third floor of the building now called Scotiabank Arena, so it could have been that. It could have been Ujiri was operating on about five hours sleep in the past three days, had just flown 14 hours from Nairobi and sprinted up to the press conference after a quick shower downstairs in the Raptors locker room. It could have been because he had too much coffee.

But as a metaphor, Ujiri sweating while making his case fits pretty well.

There was more awkwardness. Had Leonard – and Danny Green, the forgotten piece coming from San Antonio in the deal – arrived in Toronto for the physicals yet?

This was not a filler-type question. The trade can’t be made official until the Raptors sign off on a first-hand physical examination of Leonard. That’s no routine thing given Leonard missed 73 games last season with a mysterious thigh injury that was diagnosed and treated differently by the Spurs and by Leonard’s medical team. The disconnect was the primary reason the relationship between the two-time defensive player of the year and the Spurs broke down after seven seasons.

“All I’ll say is without all this medical drama that there is, we have no chance of talking to a player like that. Zero. You have no chance,” Ujiri said. “He would be signed to [a deal in San Antonio], and we wouldn’t have a chance to get him. This is why we have a chance. This was the risk that we are taking. We looked at some of the medicals as soon as the deal was done and the rest will depend on the physical that will be done shortly.”

How much better would everyone feel about Leonard’s acquisition if Ujiri had been able to say Leonard has passed his physical or even that he’ll be in Toronto on Monday to be examined?

That there is still some uncertainty around that issue plays into the larger concern around the deal which is that Leonard – who can be a free agent next summer and who left an opportunity for a five-year, $221-million payday on the table in San Antonio in order to help push for a trade to his native Los Angeles – has no interest in being in Toronto this season, let alone any season after that.

Ujiri couldn’t quite put that one to bed either.

“He didn’t express a lack of interest about playing in Canada to me,” Ujiri said. “I haven’t gotten that sense from Kawhi Leonard or his people and I’m going to give him that chance when we meet face to face.”

When? Well, no one knows that either. He’s confident in his salesmanship and belief in Toronto as a first-class NBA city more than most people who’ve been here their entire lives. But Ujiri wasn’t sugar-coating anything. It will be a challenge and it will take time even though there’s not a lot of that.

“That’s my job and I think that’s why I’m in this seat is to try and figure that part out,” he said. “I’ve had conversations with Kawhi, with his agent, with his uncle and everything has gone well. I’m looking forward to meeting with them face to face.

“Our responsibility is to figure it out and to make them as comfortable as possible and, on his part, hear more on what he wants in our team, in the future, and go from there. I take responsibility for that and I’m confident. I think we have a good game plan and we’ll see how that goes.”

But Ujiri was his most emphatic speaking about what he knows best – the seeming inability of the group that finished last season to raise its level in the playoffs, a shortcoming that can fairly be laid at the feet of DeRozan, among others.

The decision to deal DeRozan wasn’t the expression of his frustration of the Raptors being swept by the Cleveland Cavaliers this past May. It was an acknowledgement that the core group’s sub-.500 playoff record was indicative of a team that wasn’t going to be good enough.

“If we didn’t do anything, I think everybody would be pounding on we didn’t do anything and it’s the same team so what’s the difference?” said Ujiri. “We’re going to play the regular season and we’re going to get beaten again in the playoffs. That would be the narrative going into the season.”

The narrative is different now. Dramatically so, and while Ujiri was prepared to apologize for his “miscommunication” with his star player, he wasn’t about to back up on why he has flipped over two of the franchise’s cornerstones (firing long-serving head coach Dwane Casey being the other) in the space of two months.

“We’ve been doing this for how many years?” he said. “You can’t keep doing the same thing over-and-over again … I think we’ve given a chance to his team. We tried to build it up as much as we can. But at this point, we got to this level, this opportunity came in front of us and we had to jump on it.”

There will be more questions, if not always simple answers. But Ujiri couldn’t have been any clearer about why the DeMar DeRozan era had to come to an end.

And he was making no apologies for that even if was still too soon to celebrate it.

When submitting content, please abide by our submission guidelines, and avoid posting profanity, personal attacks or harassment. Should you violate our submissions guidelines, we reserve the right to remove your comments and block your account. Sportsnet reserves the right to close a story’s comment section at any time.