Losing VanVleet is a low point for Ujiri, Raptors

TORONTO – Masai Ujiri was a top lieutenant under then Raptors general manager Bryan Colangelo when Chris Bosh left Toronto to join forces with LeBron James and Dwyane Wade in Miami more than a decade ago.

He felt the sting firsthand, he saw how losing a prominent player for nothing could set a franchise back, and when he got his own GM gig in Denver later that summer he promised himself that he would never let it happen again.

It’s something that’s been top of mind for Ujiri early and often over his illustrious career. He thought about it while navigating Carmelo Anthony’s trade request – his first big test as a lead executive – and despite working from a position of minimal leverage, he turned the disgruntled Nuggets star into an impressive haul of young players and draft picks. He was conscious of it whenever Kyle Lowry or DeMar DeRozan were approaching free agency with the Raptors, making the correct call each time.

In some cases, it’s been unavoidable – they were obviously going to let Kawhi Leonard’s free agency play out rather than trading him during his lone (title-winning) season with the club. But generally speaking, he has prioritized asset management above all else. Read the player, read the market, act accordingly, and more often than not, it’s panned out.

This time it didn’t.

Up until the moment Fred VanVleet made his decision Friday night, the Raptors remained confident that they could sell their starting point guard and the prize of this summer’s free agent class on a return to Toronto. They met with him in Los Angeles shortly after the market opened at 3:00 p.m. local time and hoped that their shared history – and perhaps dangling an extra year of guaranteed money – would be enough to compete with a mega offer from Houston.

But after seven memorable seasons together, VanVleet decided it was time to move on, agreeing to sign with the Rockets for a reported $130 million over three years. Considering how his remarkable journey began – scrapping and clawing his way onto Toronto’s training camp roster and making roughly $500,000 as an undrafted rookie in 2016 – it’s hard to begrudge the business-savvy 29-year-old for siding with the highest bidder.

You can also understand the Raptors’ reluctance to match a contract at that price, given their proximity to the luxury tax and the other financial commitments they’ll have to make over the coming years. Ujiri wanted VanVleet back but not at any cost. He and general manager Bobby Webster went into negotiations with a number in mind, one that they couldn’t and wouldn’t cross. If Houston was willing to use the bulk of its league-high $66 million in cap space to max out the veteran point guard, their hands were always going to be tied. There’s no shame in that. What they may come to regret, if they don’t already, is backing themselves into a corner to begin with.

There weren’t many people expecting them to be buyers at last February’s trade deadline. They were in the midst of a disappointing season, hovering around a play-in spot and armed with some of the most coveted players in basketball. But instead of capitalizing on a seller’s market, as many around the league thought they would, the Raptors opted to keep their core together and give up a lightly-protected first round pick to address a long-time need in re-acquiring centre Jakob Poeltl.

Suffice to say, they weren’t blown away by any of the offers for their vets. As a pending free agent, the market for VanVleet was scarce. Multiple contending teams checked in and expressed interest but wouldn’t part with the type of assets Toronto was looking for, fearing VanVleet would amount to a three-month rental. The Raptors had encountered something similar with Lowry at the 2021 trade deadline, ahead of his free agency. So, they made the same decision, to hang onto VanVleet in the hopes of re-signing him or retaining some value in a sign-and-trade.

They were confident that they could keep him at a price they felt comfortable with, something in the neighbourhood of $90 million over three years. Failing that, they believed that the teams he would be most interested in playing for – contending teams without the cap space to sign him outright – would be willing to give up as much or more than they were at the deadline in a sign-and-trade. That’s how things played out with Lowry, when the Raptors helped facilitate his move to Miami and got a player they liked, Precious Achiuwa, back for their trouble. According to multiple sources with knowledge of their thought process, they didn’t view Houston as a real threat until very recently, despite its abundance of cap space and reported interest in VanVleet.

On the surface, it does seem like a strange fit. VanVleet is a fierce competitor, the type of player who has won at every level. If last year or the Tampa season are any indication, he doesn’t have much patience for losing, and as currently constructed, the rebuilding Rockets are further from contention than Toronto is. With a new head coach and an aggressive owner hoping to expedite the process, Houston was said to be in the market for a veteran guard, an adult to add to an otherwise young locker room. The Raptors never imagined VanVleet would be interested in that sort of gig.

However, with Ime Udoka at the helm of an intriguing core that features Jalen Green, Alperen Sengun, Jabari Smith Jr. and Amen Thompson, the fourth-overall pick in last week’s draft, the Rockets have the makings of a team on the rise. Mostly, though, money talks. For a player who has bet on himself so many times that its become his (branded) mantra, $130 million speaks loudly.

For Ujiri and the Raptors, this was a misread of the player, a complete misread of the market, and the type of asset management blunder that is extraordinarily difficult to recover from.

They had already lost four key players from that 2019 championship team for no return, but with the unique nature of their exits, you might be willing to give them a pass on each one. Leonard always seemed Los Angeles bound – it was baked into the price to acquire him. They were only going to pay the tax for Danny Green if Leonard returned. They weren’t willing to give Marc Gasol or Serge Ibaka multiple years of guaranteed money at their age and other teams were. All those losses add up and have contributed to the depletion of their organizational depth. Still, this is the one that the franchise might feel for a long time. This is the loss that could really hurt.

Regardless of how you feel about VanVleet as a player, losing him for nothing was always the nightmare scenario. He was the only reliable point guard on a team that lacked half-court playmaking. He was one of the only proven shooters on a team that struggled to shoot. Even in a down season, by his all-star standards, he averaged 19.3 points, 4.1 rebounds and a career-high 7.2 assists in 2022-23. Replacing his on-court production won’t be easy, and that’s not to mention everything he brought off the court as a leader, culture builder and franchise cornerstone.

The Raptors don’t have cap space to go out and chase another big-name free agent, even if they were somebody out there worth chasing. Several of the cheaper fall back options were already off the board by the time VanVleet made his decision, with Miami’s playoff hero Gabe Vincent going to the Lakers and gritty journeyman Jevon Carter landing with Chicago.

They wasted little time in using their mid-level exception – $26 million over two years – on veteran point guard Dennis Schroder, a solid addition under the circumstances but a clunky fit on a team that needs shooting, and somebody who would’ve looked a whole lot better as a backup to VanVleet than a VanVleet replacement.

They also re-upped Poeltl for four years at $80 million, a fair price for a good player who made the team noticeably better last season. Still, not unlike deadline day, it’s hard to get excited about a solid, albeit unspectacular, fundamentally sound centre given the uncertain direction of the team.

What comes next remains a mystery. Pascal Siakam and O.G. Anunoby are heading into contract years, both eligible for extensions this fall and due for big raises next summer. Gary Trent Jr., who recently picked up his player option for next season, is reportedly nearing a long-term deal to stay in Toronto. With VanVleet gone, Scottie Barnes should see his role continue to grow, perhaps as the de facto point guard. Are they running it back with some patchwork at what was already their weakest position, or are they pivoting to a more youth focused future under new head coach and player development guru Darko Rajakovic? It’s still unclear.

With his track record, Ujiri deserves the benefit of the doubt until we see what this team looks like in the fall – we’re mere hours into the NBA off-season, after all. There’s plenty of time to make this make sense.

But as the calendar flips to July, this roster looks eerily similar to the middling group that went 41-41 under Nick Nurse last season, minus a franchise icon who will surely be missed.