VanVleet left and the Raptors got nothing. The habit must stop

As an exercise in wealth management, it was an abysmal failure.

If you’re in a charitable mood, you could make the case that the Toronto Raptors were simply unlucky to lose Fred VanVleet in free agency over the weekend. Perhaps they can’t be blamed for being blindsided by the maximum bombshell offered by the Houston Rockets, who stole VanVleet from the franchise that gave him his NBA start, not to mention an NBA championship.

The Raptors certainly won’t be criticized for declining to match the three-year contract worth a staggering $130 million US that lured VanVleet to Houston. That’s a big bag of money the 29-year-old VanVleet will earn for being the grown-up in the room on an overwhelmingly young Rockets team. Then again, keeping new teammate Dillon Brooks in line — or, more likely, explaining Brooks’ next suspendable misstep to the media — is an awfully big task.

There is always context when players go. There is always a reason to let them go. But if you trace the devolution of the Raptors franchise, from their crowning championship performance in 2019 to their recent bit of hard luck in the offseason, there is at least one through line.

As it was with Kawhi Leonard and Danny Green and Serge Ibaka and Marc Gasol, so it was with VanVleet. The Raptors lost each of them to free agency for what amounts to nothing. In the ongoing dismantling of what remains of a championship team, the Raptors have received very little in return for some of their best players. At least Kyle Lowry’s departure to Miami in 2021 brought back Precious Achiuwa, who is still only 23 and possesses theoretical upside.

That’s not to say the Raptors didn’t do everything in their power to change the outcomes of some of the other exits. Leonard was certainly offered a king’s ransom to stay in Toronto. Green could have been kept around if Leonard would have stayed. And who knows what might have happened if the Raptors, who undoubtedly would have been favorites to repeat as champions in 2020, would have kept that band together.

Plan B, of course, was to keep options open for Giannis Antetokounmpo — a dream that, while it may never die, has been carried by the Greek freak who committed to being a Milwaukee Buck until at least 2025. And keeping those options open came with a cost.

Still, this year’s free-agent fiasco didn’t have to end like this. VanVleet was a commodity at the trade deadline in February, with the Raptors choosing to flip him for the best available offer, just as the Raptors chose to flip Lowry a few seasons prior. If every move a manager makes, or doesn’t make, amounts to a gamble, let’s just say the denizens of Toronto’s front office are on a decidedly cold streak. Signing Dennis Schröder as VanVleet’s replacement, given how Schröder only adds another spotty shooter to Toronto’s vast collection of such, didn’t come close to making up for the latest loss.

“The way I look at the deadline — it’s really not a good place to make long-term decisions,” Raptors president Masai Ujiri said back in February. “Hopefully we can have a little patience. Everything we could have done today, we could maybe do in the summer.”

Well, summer is here. And you’ll excuse the fan base if it lacks patience. No one doubts Ujiri’s ambition. Recently, however, it has become easier to question his vision. When it comes to reading players and anticipating markets, he hasn’t proven particularly prescient.

That probably doesn’t worry Ujiri, who is still armed with job security and bottomless swagger. He knows better than anyone that everything can change in one big move. And in a league where there are no sure things — where the eighth-seeded Miami Heat represented the Eastern Conference in the NBA Finals — you can understand why Ujiri has operated as if he’s constantly waiting for the next superstar to be unleashed.

Still, it goes without saying that Ujiri will have to be especially careful how he handles another pair of holdovers from Toronto’s title-winning era — specifically Pascal Siakam and OG Anunoby. Both are entering the final years of their respective contracts. And it’s certainly possible that both could remain in Toronto beyond those deals.

Siakam has threatened as much — or so suggested a TNT report in the lead-up to last week’s draft that claimed there is a “growing sentiment” Siakam would not re-sign with the theoretical team trading for him. That tells you Siakam is worried he might be moved and is looking to assert some influence. After all, staying in Toronto provides his most likely path to achieving the NBA status that would qualify him for the so-called super-max contract extension. And there’s a lot to like about being a top offensive option on a team that lacks offensive firepower.

But if the Raptors have been an in-between team with Siakam as their center, what are the odds that they will improve when Siakam, who turns 30 next season, becomes more expensive?

Anunoby, on the other hand, has played through persistent reports that he is unhappy with his role in Raptorland, specifically on the offensive end. Perhaps with VanVleet out of the picture, there will be more details for Anunoby and others. There are certain voids that need to be filled. Shooting is the obvious one. Playmaking and half-court know-how also come to mind, as do late-clock shots.

Perhaps Darko Rajakovic’s presence as a rookie head coach will change the tone and look. Maybe Scottie Barnes, learning from the mistakes of his uneven sophomore season, will re-establish himself as a star worth building around. But if Ujiri didn’t like watching last season’s Raptors team play, as he admitted in his end-of-season press conference, it’s hard to imagine why the current roster as it sits will produce a decidedly better one product.

Which suggests that more trading needs to be done, where long-term asset management needs to be taken more seriously than it has ever been. If Siakam and/or Anunoby aren’t part of the long-term plan, it’s critical that they produce returns to support it. As the Raptors have come to learn the hard way, it’s nearly impossible to rebuild a team into anything when free agent after free agent leaves for next to nothing.

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