Former Raptors' success a reminder of the road not taken

In the summer of 2022, with a surprising 48-win season and a playoff appearance in the rear view, it seemed like the Toronto Raptors championship era was close enough to cast a warm glow on everything. There was hope that better days were ahead, that the Raptors could successfully extend their competitive window without the indignity of a bottom scraping rebuild.

There was good reason to believe.

Scottie Barnes, drafted fourth overall in 2021, and the prize of the "Tampa Tank" in 2020-21, had just earned recognition as the NBA’s Rookie of the Year.

Pascal Siakam was named all-NBA for the second time in his career and had just turned 28.

Fred VanVleet had been named an all-star and was also 28.

And while OG Anunoby hadn’t yet earned formal recognition as an all-NBA defender and one of the best 3-and-D wings in the NBA, anyone who watched the six-foot-seven, 230-pounder play on a nightly basis knew it was simply a matter of time. Sure enough, Anunoby got a second-team all-defence nod in 2022-23 at age 25.

The roster wasn’t perfect — it lacked size, depth and perimeter shooting, all of which proved problematic as Toronto slumped to 41 wins and a Play-In loss in 2022-23 — but it wasn’t short on quality.

And the proof of concept — unfortunately for Raptors fans — has only come now, two years later, with Toronto’s three championship holdovers on different teams, enjoying a level of success the current Raptors can only aspire to right now.

VanVleet, who left the Raptors in free agency in 2023, emerged as the veteran leader on a young Houston Rockets team that won 52 games this past season and earned the second seed in the Western Conference before being eliminated in the first round of the playoffs. They are seen as a team on the rise.

Closer to home — literally and figuratively — Raptors fans can watch Siakam and Anunoby compete as cornerstone pieces for the Indiana Pacers and the New York Knicks, respectively, as they meet in the opening game of the Eastern Conference Finals on Wednesday night.

It’s hard not to think ‘what could have been.’

Instead the Raptors have won 25 and 30 games the past two seasons as part of a hasty rebuild that will be expected to bear fruit this coming season, given the club will have a projected starting lineup with a combined salary of $156.5 million — the salary cap is $154.6 million — and an average age of 27, which is ‘go time’ in NBA years.

How would a Raptors lineup featuring VanVleet, Siakam, Anunoby, Barnes and Poeltl fare in an Eastern Conference that’s hardly a murderer’s row of contenders?

Well, the spacing would still be iffy, the depth questionable, and it would not be cheap, with the mystical starting five earning  $152.2 million this year, jumping (theoretically) to $188.3 million next season when Barnes’ max deal kicks in.

But you’d have to think they would have been a factor.

Why it didn’t work and why it all ultimately unravelled in the space of 16 months is both well-known and as yet still unspoken.

The broad themes as I’ve reported previously: tension between VanVleet and Barnes, Anunoby chafing at his role in the offence, Siakam frustrated and ultimately dismayed that he wouldn’t get the contract he believed he deserved, a general hesitation to compromise for the larger project, and a head coach, Nick Nurse, who wasn’t comfortable tackling the various friction points head on. Meanwhile, the roster was woefully short of talent beyond the starting lineup as management went on an uncharacteristic cold streak when it came to backfilling the roster with young rotation players on cheap contracts.

VanVleet spoke to it last season after he had signed with Houston for $83.7 million guaranteed over two seasons, rejecting a Raptors offer that was reported to be three years at $90 million with a $10 million guarantee for a fourth year.

“You could feel the shift … I know the Raptors, we feel like we're the only team in the NBA (going through this), but it's not specific to that team. There's a lot of teams going through it where you're trying to win, you're trying to build, you got young guys, you got a couple of vets and you're just trying to figure it out,” VanVleet said in Houston to a small group of reporters from Toronto. “I think you could just kind of feel the dynamic shifting a little bit (last year; 2022-23). When things kind of went a little different than what we're used to in terms of our culture and just the day-to-day, that's when I was like, 'OK, I know Masai (Ujiri) is not going to deal with this forever.' That's when you kind of knew things were going to change eventually.”

The Raptors weren’t oblivious to the talent they had. According to multiple sources, there were several efforts to find ways to keep the core group together.

There was a meeting in Miami in the summer of 2022 where Barnes, Siakam, VanVleet, Anunoby and Achiuwa sat down with each other and Ujiri and general manager Bobby Webster in an effort to gauge how tenable it would be to push forward with the group, but a commitment wasn’t forthcoming. That the players all went their separate ways into the Miami night was noted.

VanVleet and Siakam turned down extensions before the season started, and the Raptors knew that Anunoby would test free agency in the summer of 2024 since his performance exceeded the market value of the most the Raptors could offer him under league rules.

Things only got worse as the 2022-23 season started, with a string of injuries exposing the Raptors' lack of depth, and their lack of size and shooting requiring them to play a high-risk defensive style, giving them a success rate that was mostly feast or famine.

There were more meetings that bore little fruit, on-court bursts of frustration and as the trade deadline approached, some players almost hoping to be moved and others agitating to add a centre to bolster a porous defence. Rather than sell, the Raptors added Poeltl, but by then it was almost too late. 

It was no one’s shining hour. It cost Nurse his job, while Ujiri’s image as the ultimate behind-the-scenes fixer and culture setter took a hit.

“Sometimes there comes a time when there’s a little bit of complacency, I think. When there was a little bit of complacency with us, I think some selfishness seeped in,” Ujiri said in April of 2023 after announcing the departure of Nurse. “… I personally don’t think contracts were an issue because historically here the players know that we’ve taken care of the players here. There’s been barely any players that (we haven’t taken care of). That’s kind of what we do, we like continuity here. So I didn’t see where that was an issue. But some people would say accolades and all the different things that players can get or what they’re gunning for.

“But yeah, selfishness, I mentioned it before, and I think the players know that, they know. Did that happen because of the system or different things that we did, or was it them individually? Again, I’m not going to point fingers now. I just want to know how we’re going to do better. And whoever wants to do better, whoever wants to play the right way, whoever wants to win, whoever wants to win is going to come with us.”

Still, the Raptors had a core of Anunoby, Siakam, Barnes and Poeltl to start the 2023-24 season, an All-NBA defender (Anunoby), an All-NBA wing (Siakam), and an all-star wing (Barnes) along with Poeltl, a proven NBA centre.

But it wasn’t working. Ujiri doubled down on his ‘selfishness’ broadside on the eve of training camp, which didn’t sit well with the returning core. The long-drawn-out contract dance between Siakam and Ujiri had hurt the relationship they had previously enjoyed — it’s telling that Siakam’s voice was conspicuously missing in the flurry of documentaries that were made to celebrate the Raptors' 30^th anniversary season, and Anunoby was more determined than ever to test free agency. The roster remained short of supporting talent.

In the end, the only ones that remain are Poeltl, the former Raptor who was re-acquired at the trade deadline in 2023 in a last-ditch effort to bolster the pre-existing core and Barnes, who management projected as the centrepiece who could raise the Raptors ceiling, a calculation that on some nights looks obvious and on others — when his still nascent offensive game fails him — looks optimistic.

Anunoby (along with Precious Achiuwa and Malachi Flynn) was traded on Dec. 30, 2023, to the Knicks in the deal that brought Immanuel Quickley and RJ Barrett to Toronto, along with the draft pick the Raptors used to select Johnathan Mogbo.

Barely two weeks later, the Raptors traded Siakam to the Pacers for a deal that included Bruce Brown and three first-round picks, which in the end resulted in the Raptors having Brandon Ingram, Ja’Kobe Walter and Ochai Agbaji on the roster for the 2025-26 season.

There are plenty of ways to rationalize the Raptors moves: Toronto didn’t believe they could resign Anunoby, so adding two young starters was good value, or in trading Siakam Toronto ended up with a player of comparable talent (Ingram) who is three years younger and signed on a cheaper deal, along with two younger players still that look like they could be rotation pieces in the near future. How that move looks will depend heavily on whether Ingram can come close to matching the 76.3 games per year Siakam played in his age 28, 29 and 30 seasons, which seems optimistic given Ingram has played just 127 games in his last three seasons.

And if the measure is winning basketball, so far, the Knicks and the Pacers (and Rockets) have the better ends of the deals. The Pacers have made the Eastern Conference Finals in consecutive seasons with Siakam as the co-star for Tyrese Haliburton, while the Knicks advanced to the second-round last season and all the way to conference finals for the first time in 25 years with Anunoby fulfilling his potential as one of the best two-way role players in the sport. The Rockets appear to be a move or two away from being a juggernaut.

The as assembled Raptors — with the addition of the No. 9 pick in the upcoming draft — will have their chance to get into the competitive mix in the muddled East this coming season. They project to be younger and deeper than the roster they could have had. And in terms of selfishness? The team has set franchise records for assists in consecutive seasons under head coach Darko Rajakovic. The vibes are good, even if the wins have been scarce.

But watching as Anunoby and Siakam battle for Eastern Conference supremacy, and VanVleet’s Rockets reflect on a breakout season, it’s clear that the bar for the Raptors' path over the past three seasons being deemed a worthy one is high.