DA's Morning Tip

Masai Ujiri takes bold gamble on Toronto Raptors' title potential with Kawhi Leonard trade

Toronto's top basketball executive avoids status quo, makes blockbuster swap

Life often provides juxtaposition.

Last Monday afternoon, Masai Ujiri was in Nyang’oma Kogelo, a small town (population 3,648) on the western edge of Kenya, spending some quiet moments with the 44th President of the United States. The basketball executive and the former Chief Executive were both there to help open a vocational center and sports and training facility that Barack Obama’s half sister, Auma Obama, will run through her foundation, Sauti Kuu.

Obama went on to South Africa, where he addressed a cheering throng in a cricket stadium just north of Johannesburg, and delivered the annual Nelson Mandela Lecture on Wednesday. Previous lecturers have included former president Bill Clinton, Nobel Prize winner Archbishop Desmond Tutu, Microsoft co-founder Bill Gates and assorted presidents of nations and human rights activists.

Ujiri stayed in Kenya and traded DeMar DeRozan.

The former’s words were carried live and summarized in newspapers, magazines and online forums around the world. The latter’s set NBA Twitter on fire last Wednesday.

Obama noted that Mandela, lionized and beloved after 27 years in prison in South Africa — and then rose to run South Africa as its president — could have ruled the country for life. “Who was going to run against him?,” Obama asked during the lecture. “… But instead he helped guide South Africa through the drafting of a new constitution, drawing from all the institutional practices and democratic ideals that had proven to be most sturdy, mindful of the fact that no single individual possesses a monopoly on wisdom.”

Ujiri, still firmly in charge of the Toronto Raptors as President of Basketball Operations (and a son of Africa himself), merely has gambled his job in a nation with an inferiority complex the size of … well, Canada … that he can convince Kawhi Leonard to stay in Ontario and not go to Los Angeles in a year’s time. Only the immediate future of Canada’s only NBA team lies in the balance.

And speaking of that word — lies…

Will we ever know exactly what Ujiri said both to DeRozan, the best player in franchise history (all due respect to Vince Carter), and to DeRozan’s representative in separate conversations in Las Vegas earlier this month at NBA Summer League? And even if we had a verbatim transcript, would we ever be able to reconcile the two different recollections of the conversations?

We appreciate him and I promise you that we’re going to celebrate him in the best possible way that we can as long as I’m here.””

Masai Ujiri, on DeMar DeRozan

DeRozan and his camp are adamant that Ujiri said he would not be traded — which, obviously, he was, a week later — and have called him a liar, explicitly and implicitly (DeRozan’s Instagram posts make his position on the issue crystal clear.) Ujiri wasn’t quite as adamant in his press conference Friday, which began a couple of hours after Ujiri had arrived back from Africa, barely giving him time to shower and dress. But he was clear, even as he apologized to DeRozan for “a miscommunication,” he was equally clear that all he told DeRozan and his camp at the time was that no trade was imminent.

Still, Ujiri apologized to DeRozan in his first public remarks since the trade last Friday.

“I want to not only apologize to DeMar DeRozan for maybe a gap of miscommunication but also to acknowledge him and what he’s done here with the Raptors, for this city, for this country,” Ujiri said. “There’s no measure to what this kid has done. We appreciate him and I promise you that we’re going to celebrate him in the best possible way that we can as long as I’m here.”

In an era where so many feel it’s a fait accompli that the Golden State Warriors are unbeatable, Ujiri’s drive to not settle, to go all-in, to take a shot — albeit a long one — at shaking up a good team in hopes of making it great is admirable.

Trading a four-time All-Star, even for a top-five player (when healthy), is not a guarantee of success, and is a bigger gamble when Leonard made his geographic preferences going forward clear. But Leonard is that good, and he just turned 27. DeRozan will be 29 when the 2018-19 season opens and his backcourt mate, road dog and fellow All-Star, Kyle Lowry, will be 32. Keeping DeRozan, at the least, would mean giving him another big contract in 2021, when he’ll be 31.

But was Ujiri too keen to bust up a team that, while not likely to have been a dominant, intimidating squad even in the post-LeBron Eastern Conference, was certainly capable of putting together a Finals run in the next year or two? It’s hardly a secret that Ujiri wears his heart on his sleeve in so many things, from his big brother demands of the kids he has selflessly follow a path from their countries in Africa to the States and other western nations through his Giants of Africa program, to his profane outbursts against Raptors’ opponents in the playoffs (“Bleep Brooklyn” in 2014 and “we don’t give a bleep” about Paul Pierce’s trolling in 2015), to his postgame (and, to be fair, private) anger at his own team’s poor performances, which included both former coach Dwane Casey and DeRozan over the years.

No one’s ever put together the type of talent Golden State has amassed. Most good teams are like Toronto has been — one led by one All-Star, maybe two.

The Raptors were in the second group. They have won 263 regular-season games the last five seasons — by far, the most in the Eastern Conference. (However, if you add up LeBron’s last five seasons — his last with the Miami Heat in 2013-14, then his four seasons in Cleveland, his teams combined to win 265.) They were a really good team that ran into an all-time, Hall of Fame player — the same way the Milwaukee Bucks ran into Larry Bird in the early to mid-1980s, the same way the Cavaliers ran into Michael Jordan in the late ‘80s and early ’90s, the same way the Sacramento Kings ran into Kobe Bryant and Shaquille O’Neal as the 2000s began.

That is the outcome for many, if not most, solid, well-coached teams. A team like the 2010-11 Dallas Mavericks occasionally breaks through — when it has a strong roster, a great coach and a some luck — and wins it all. But most 50-win teams don’t.

But the Raptors pulled the trigger, anyway. They thought about status quo-ing it with a team with Lowry and DeRozan in reduced roles in a year or two, if their young players develop as they believe they will. But that didn’t seem realistic, either.

Every child of five who’s ever played telephone knows how words, and meanings, and inferences, can be garbled — even if they don’t know what “inferences” means. The net-net remains that DeRozan is now with the Spurs, along with second-year big Jakob Poeltl, and Leonard is in Toronto, along with veteran guard Danny Green.

The Spurs knew they had to move on from Leonard, once he made it clear he wanted out of San Antonio. The only question was where they would send him. It wasn’t pleasant to contemplate moving a Finals MVP and the Spurs’ franchise player, but there was no turning back.

The Raptors had concluded they couldn’t tinker around the margins anymore, even with a team that had won a franchise-record 59 games last season, with a coach in Casey who would go on to be named Coach of the Year — two months after Ujiri fired him. They believed the Lowry-DeRozan led team had gone as far as it could — and even though their chief tormentor the last three years, LeBron James, left the East and signed with the Lakers, Toronto did not believe anything would change going forward.

There sat the Celtics, rising in the East, with Jayson Tatum and Jaylen Brown, and the Philadelphia 76ers coming of age with Ben Simmons as well — all long, athletic players the Raptors feared could lock up DeRozan in future postseasons, while he got older. The memories of him going 3 of 12 against the Cavs in Game 3, and getting benched the final 14 minutes of yet another loss to LeBron, then getting ejected with Toronto down 30 in the Game 4 clincher, were still fresh.

DeRozan had been good, but not All-Star great, throughout most of his five playoff appearances in Toronto.

Against Brooklyn in 2014, a seven-game series loss, he’d averaged almost 24 points per game in the series, but shot less than 39 percent, too. The next year, Toronto got swept by the Washington Wizards in the first round, and DeRozan’s average dipped to 20.3 points per game, on 40 percent shooting.

Both DeRozan and the Raptors had their best postseason success in 2016, when they reached the Eastern Conference finals. Against Indiana in the first round, DeRozan had 34 points in the crucial fifth game of a 2-2 series, then went for 30 in the decisive Game 7. Against Miami, he had 28 and 8 in Game 7, a 27-point Raptors rout that got them to the conference finals.

But, from that point on, LeBron and the Cavs gutted the Raptors’ psyche.

In ’16, Toronto had Cleveland tied 2-2 in the conference finals. But in perhaps the biggest game in franchise history, Game 5 in Cleveland, the Cavaliers smoked the 116-78. DeRozan was 2 of 8 from the floor. And Cleveland closed Toronto out in six games.

In 2017, James averaged 36 points, 8.3 rebounds and 5.3 assists in a four-game sweep of Toronto in the Eastern Conference semifinals. The Cavs won each game by an average of 15.3 points per game.

And this year, of course, was the coup de grace, with Toronto blowing a 14-point first-quarter lead in Game 1 and a 10-point lead with 10 minutes left in the game. There was the too crazy to be believed sequence in the final seven seconds of regulation, with the game tied at 105, when Fred VanVleet missed a 3-pointer, DeRozan missed a putback, C.J. Miles missed the putback of that miss, then missed another putback of his miss, and Jonas Valanciunas missed a tip in. All in seven seconds. The Cavs would then beat the Raptors 113-112 in OT.

And that’s why, as The New York Times’ Marc Stein first reported, the Raptors let it be known around the 2018 Draft that their veterans –Lowry, DeRozan, Serge Ibaka and Valanciunas — were available, while none of their core young players — guards Fred Van Vleet or Delon Wright, and forwards O.G. Anunoby and Pascal Siakham – were not. The Raptors were ready to turn things over completely to their young guys, if need be.

But Lowry, at more than $30 million per year through 2020, had precious few suitors. Ditto for Ibaka (almost $45 million left on his three-year, $65 million contract, also through 2020) and Valanciunas (two years and $34 million left, including a player option in 2019-20).

That left DeRozan. But the Raptors did not believe the Spurs were all that interested. They’d been talking round and round with Philly and the Lakers (not so much Boston, but the Celtics, with their trove of young players and remaining future Draft picks, could always get deeply involved at any moment if they chose). Toronto was on the list, too, but the discussions were stagnant. The Spurs were asking about Anunoby, a potential Leonard clone, as well as another future first, which continued to be a non-starter.

But, teams always continue dialogue, even when the trade trail goes cold. So San Antonio and Toronto kept talking, at lower management levels, while NBA Summer League began. It was in Vegas where Ujiri met DeRozan and DeRozan’s agent, Aaron Goodwin, separately. The meeting with Goodwin, per sources, was planned. Running into DeRozan at Cox Pavilion, after one of the Raptors’ games, was not. Ujiri and DeRozan spoke briefly — less than five minutes.

Sources with knowledge of each of the talks generally concur that Ujiri said no DeRozan trade was imminent, and that he wanted to know what DeRozan was going to do this summer to become a better performer in the playoffs. What is in question is whether Ujiri assured DeRozan there would be no trade at all, or if he promised Goodwin and/or DeRozan they would be contacted if things changed.

Asked about the discussions this weekend, Goodwin said: “this is a business and more and more players are starting to understand they are only as good as the last game that they have played for some of these owners, presidents and GM’s. Not all, but some. Some will treat a player and their family and representation with respect, others don’t even return phone calls. DeMar to this day still has not heard anything from ownership.”

After Vegas, Ujiri went on his trip to Africa and the meeting with President Obama and Auma Obama. But San Antonio hadn’t made any headway with Philly and was still extremely reluctant to trade Leonard to the Lakers. There weren’t many options. And the specter of Leonard going to the USA Basketball minicamp this week in Las Vegas, with Gregg Popovich also there in his first official appearance as the U.S. team’s coach, was not what anyone wanted to endure.

Whatever the timetable, the sides began moving toward one another. The Spurs dropped their request for another pick. The Raptors included one of their young guys in Poeltl. It came together, quickly.

San Antonio had resolution, finally. DeRozan, a class act and hard worker, will provide a potent one-two punch with All-Star LaMarcus Aldridge. The Spurs hope Dejounte Murray makes a big jump in his first full season as a starter, without the specter of a Hall of Famer in Tony Parker behind him. The Spurs will figure it out without Leonard. They had a lot of practice doing so last season.

Toronto, though, begins watching the clock. The Raptors have a sales job in front of them.

They think they check all the boxes in which Leonard will be interested — strong ownership, organizational purpose and infrastructure, a culture of defense, a rabid fan base, a fabulous, cosmopolitan city that nonetheless won’t smother a basketball player the way it might, say, John Tavares. (Longtime San Diego reporter/columnist Mark Zeigler wrote Sunday that the Raptors’ chances of keeping Leonard may be better than people think.) His first visit, replete with smiling photo, was one step. A million more follow.


Yes, other teams have had to make difficult calls on star players. Boston moved Isaiah Thomas after an MVP-caliber season in order to get Kyrie Irving. Miami decided there was a price it was not willing to pay to keep Dwyane Wade in 2016 (though it got him back last February, after stops in Chicago and Cleveland).

But DeRozan was the first star in the Raptors’ history who never asked to be traded, never had a foot out the door, never broke Toronto’s heart by wanting to be elsewhere. He didn’t even take a free agent visit in 2016, agreeing to a five-year deal with the Raptors almost immediately. He repped the team that took him in the first round in 2009, and would have had no problem playing his whole career there.

He was loyal to Toronto, which built a team around him that became one of the NBA’s better teams. But not its best. And so loyalty had to take a back seat to cold calculation. The Raptors are putting their chips and their essential body parts in the middle of the table, no longer satisfied with being good, even very good. They will either be great or they will rebuild, all on the word of a man who, unlike the 44th President of the United States, doesn’t have much to say at all.

* * *

Longtime NBA reporter, columnist and Naismith Memorial Basketball Hall of Famer David Aldridge is an analyst for TNT. You can e-mail him here, find his archive hereand follow him on Twitter.

The views on this page do not necessarily reflect the views of the NBA, its clubs or Turner Broadcasting.