With Damian Lillard off the table, where do the Raptors go from here?

The Toronto Raptors appeared to be a perfect destination for Portland Trail Blazers superstar Damian Lillard, who requested a trade this offseason in what turned out to be a depressed market for a 33-year-old point guard with four years and approximately $216 million remaining on his contract.

After all, the Raptors lost starting point guard Fred VanVleet in free agency this offseason and, with a glutton of defensive-wings but a lack of pull-up shooting and floor-spacing, Lillard was the perfect basketball fit and the missing piece for a Raptors team in desperate need of an offensive superstar.

Instead, the Milwaukee Bucks swooped in at the last minute to pair Lillard with Giannis Antetokounmpo, who put pressure on the Bucks front office with public statements this offseason hinting at the possibility of him leaving the franchise in the near future.

After lusting after Kevin Durant last offseason and Damian Lillard this summer, the Raptors have once again been left in the dust. So, where do they go from here?

Asset management

First of all, it’s worth considering what the Bucks sent out in the deal to acquire Lillard, and whether or not the Raptors could have exceeded that offer.

The Bucks traded an unprotected first-round pick in 2019, pick swaps in 2028 and 2030, Jrue Holiday and Grayson Allen for Lillard in a three-team trade with the Phoenix Suns. At first sight, it’s an uninspiring return for a historically healthy, All-NBA caliber guard coming off the best season of his career in which he averaged 32.2 points on 64.5% true shooting.

But giving up the rights to three first-round picks at the end of the decade is no small thing, and the Bucks completely leveraged their future in order to trade for Lillard.

The Raptors had the assets to exceed the Bucks’ offer, especially if they were willing to part ways with Scottie Barnes or O.G. Anunoby, although doing so would create another hole to plug on the roster. Still, the Raptors might have been able to beat the Bucks deal even without adding their young wings, sending a package of Gary Trent Jr., Chris Boucher, Thad Young, Precious Achiuwa, Gradey Dick and picks to Portland in a similar three-team construction with the Suns — the money works.

However, Toronto might have been hesitant to give up on their young talent before seeing what they could do in expanded roles, or with leveraging their entire future for Lillard given his relatively advanced age.

It's also entirely possible the Raptors offered a similar package but the Blazers simply liked the Bucks' offer more, coming to the conclusion that shorting the Bucks' future was wiser than shorting the Raptors' given that Antetokounmpo can still leave in free agency in 2026 and the Bucks don’t have a young cornerstone to fall back on in the same way Toronto does with Barnes.

It’s also possible that Lillard didn’t want to come to Toronto but was open to the possibility of joining Antetokounmpo in Milwaukee. There are simply too many unknown factors to fully judge the deal from Toronto’s perspective.

Still, the market was depressed enough to wonder why Toronto couldn’t figure out a way to get a deal done after their front office has spent years positioning themselves to make exactly this type of opportunistic star trade, signing veterans to tradable contracts and holding onto their future draft capital.

Adding Lillard to this Raptors team would have made the rest of their upcoming short-term decisions a lot simpler, as they would have instantly vaulted into contender status and been able to justify signing Pascal SIakam and O.G. Anunoby to long-term contract extensions, entering season 29 in win-now mode. Instead, several questions remain unanswered.

The Pascal Siakam decision

Toronto’s best player is currently in the prime of his career at age 29 and is coming off his best season ever, yet Siakam enters the 2023-24 season on an expiring contract.

His current deal is set to end in 2024, when he could be the best unrestricted free agent on the market. And he isn’t the only one: Anunoby and Gary Trent Jr. are also on expiring contracts, meaning three of the Raptors' five likely starters could enter the season as pending free agents, which is exactly how you create an unhealthy locker room culture — with players playing for stats rather than wins.

Still, a part of it is understandable. For one, Anunoby is only eligible to sign a four-year, $116 million extension with the Raptors this offseason, meaning there was likely never any path to getting a deal done with him when it makes more sense for Anunoby to wait until next summer, when he can enter free agency and sign a more lucrative contract.

Trent is eligible for a four-year extension worth up to $113.6 million, but his situation is complicated, too, since he had a disappointing 2022-23 campaign and the Raptors would be justified in wanting to see him in a bigger role before signing him to anything long-term.

But with Siakam, there is no debate. Either Toronto signs him to a long-term extension or they trade him before the season starts. Allowing him to walk into the final season of his deal unsigned is simply too big of a risk. Just ask VanVleet.

Siakam was reportedly willing to sign a max extension of four years, $192.1 million if Toronto put it on the board earlier this offseason, although it’s possible his feelings on that have changed after watching the Raptors dangle his name in trade discussions all summer — and after watching Antetokounmpo leverage his own upcoming free agency to exert pressure on the Bucks to build a championship contender around him.

With Lillard off the table, the Raptors have no choice but to re-engage Siakam in contract extension talks and to try to get him signed long-term. If not, they should see what they can get in a trade for the Cameroonian forward, because entering the year with Siakam (and two other starters) on expiring contracts calls for all sorts of trouble.

Making the most of a bad situation

As much as it stings to have missed out on the Lillard sweepstakes — especially when it appeared he was heading to Toronto up until the very last minute — another superstar will hit the trade market soon. That’s the reality of the modern NBA. And the only thing the Raptors can do is put themselves in a better position to trade for the next star that becomes available. Of course, some Raptors fans will pine for a full-out rebuild, but given everything we know about the Raptors front office, that’s not going to happen.

Instead, the Raptors need to rediscover some level of competence this season. That starts with making a decision on Siakam before the season starts. Of equal importance is not losing Anunoby for nothing next offseason, when he will be an unrestricted free agent, meaning the Raptors have to be confident he will sign a long-term contract with them next offseason, or trade him before it gets to that point. Again, they cannot risk losing a player as talented as Anunoby for nothing.

Finally, and perhaps most importantly, the Raptors and incoming head coach Darko Rajakovic have to do a better job developing their young players — the very same players they've held onto in all of these trade discussions.

Between Barnes, Anunoby, Trent Jr., Precious Achiuwa, Gradey Dick and Christian Koloko, Toronto has a genuinely exciting group of young players. But they need to get the most out of each of them in order to not only be competitive next season, but also to put themselves in a better position to make a consolidation trade down the line the next time a superstar is available.

After all, That’s how they were able to win 59 games in 2017-18, trade young players and picks for Kawhi Leonard and Marc Gasol the next season, and still have enough talent left over to win a championship in 2019.

It’s not going to be easy. And after losing VanVleet for nothing, failing to replace him in the trade market, and entering training camp with three starters on expiring deals, the Raptors have their work cut out for them. But that’s why the front office is paid the big bucks: to figure it out.

Sure, there are going to be growing pains this season. But the Raptors do have a path back to championship contention — as narrow as that path might be.