A couple of days ago, the Toronto Raptors were making a lot of noise. After months of the Miami Heat being in the driver's seat of the Damian Lillard sweepstakes, The Raptors suddenly emerged as the favorite to land the seven-time All-Star from the Portland Trail Blazers. Once again, it looked like Masai Ujiri had something up his sleeve. But when he rolled up, it didn't reveal an arm full of tricks. It revealed an arm with nothing to show for a Raptors fanbase that has gone through a rollercoaster ride over the last few years.
In the end, the Milwaukee Bucks got Damian Lillard. The Raptors, meanwhile, are left with a ton of question marks. As the 2023-24 regular season approaches, let's look at three burning questions the Toronto Raptors must answer before training camp begins on October 3rd.
The question: What's the plan?
No, seriously. There really is just one main question for the Raptors heading into the season: What is Masai Ujiri's plan for this team?
The Raptors executive doesn't seem to know what he wants for this team moving forward. The very least he can do is commit to a real direction. As it stands, this team is headed absolutely nowhere. Ujiri missed out on the Lillard trade. They missed out on the Durant trade last year. They let Fred VanVleet walk for nothing this offseason. What direction is this team headed to?
Ujiri seems to have lost his magic around the NBA circles with the way he handles business and fellow colleagues are clowning him for it, too.
“Somebody I know who’s dealt with Toronto’s front office that I talk to this week called Masai ‘the guy in your fantasy league who offers five trades a week and cancels at the last minute before you can decide whether to accept them or not.’”
– @highkin on Masai Ujiri
(Via… pic.twitter.com/2NVfUCYl06
— NBACentral (@TheDunkCentral) September 27, 2023
That is obviously not a good look for Ujiri, who has established a reputation of being one of the best executives in the NBA over the last decade.
Ujiri has made savvy moves in the past that made the Raptors one of the best-run franchises in the NBA. In fact, he made the ultimate bold move when he traded for Kawhi Leonard in the summer of 2018. The risky trade, of course, wound up winning the Raptors their first ever NBA championship later that same season with Kawhi Leonard leading the way with an all-time 2019 playoff run. Though Leonard still bounced the following summer, credit went to Ujiri for pulling off the ultimate high risk, high reward trade.
Those are the kind of moves that made Ujiri one of the best GMs in the league. But over the last few years, his decisions, particularly his unwillingness to make those kinds of bold moves, have set back the Raptors a great deal.
Let's just go back to last summer, when Kevin Durant was available in the trade market. Like with Lillard, the Raptors found themselves right in the thick of the Durant sweepstakes. However, Toronto was unwilling to include Scottie Barnes in any trade for KD.
I get it, Barnes just won Rookie of the Year. You took flak for taking him 4th overall because many thought he won't pan out in the NBA. The kid showed more than exceeded expectations in Year 1, despite all the naysayers and you proved everybody wrong. That's great and all.
But whenever Kevin Durant is on the table, you do that trade 10 times out of 10. This is Kevin Wayne Durant we're talking about.
The ship sailed, and eventually the Nets traded Durant to the Phoenix Suns during the season. Okay, time to move on.
Then, at the deadline, the Raptors had the chance to make moves and trade Fred VanVleet and Gary Trent Jr. to at least ensure they get something in return for them unless they walk away in free agency for nothing. They could have received some draft capital as well as other pieces in exchange for those two.
But Ujiri didn't sell, when the Raptors should have been. Instead, he bought. He brought back Jakob Poeltl while trading away a first round draft pick to the San Antonio Spurs. The move signified they were still looking to compete in the East, when they really shouldn't have. As it turned out, Toronto missed the postseason after falling in the play-in tournament. It would've been better for the Raptors to mail in the season and gain more assets.
And what ended up happening in offseason? Fred VanVleet received a monstrous offer from the Houston Rockets that Toronto had no chance of matching. So VanVleet bolted while the Raptors watched him go for nothing.
The VanVleet ordeal showed that Ujiri's lack of awareness of the situation cost them more assets that, in hindsight, they could have used to trade for Dame.
Sub-question following the Lillard fall out: Why are we in the thick of the Jrue Holiday sweepstakes?
I get being in the race for Damian Lillard. When healthy, Lillard is still one of the 10 to 15 best players in the NBA.
But for Jrue Holiday? For what? To top out as a first round exit? To trade him using the same assets the Raptors could have used for Lillard? Jrue Holiday, as great as he is, isn't the franchise-altering piece that will take Toronto to the next level.
A core built around Holiday, Pascal Siakam, Scottie Barnes, and maybe O.G. Anunoby isn't going to get the Raptors anywhere close to a championship. The Raptors will be a 6th seed at best and no place is worse in the NBA than being a middling team.
Another sub-question: What will happen to Pascal Siakam and O.G. Anunoby?
The Lillard sweepstakes gave this team a small glimmer of hope that they could still compete in the East with Pascal Siakam as one of the main stars of the team. Now that they missed out on Damian Lillard, this team has no choice but to blow it up.
Siakam should go. So should Anunoby. Is Masai Ujiri aware of that? Raptors fans should hope he comes to his senses.
Siakam and the Raptors have reportedly not engaged in contract extension talks. So, what's happening?
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