What Raptors could offer Trail Blazers in a trade for Damian Lillard

It hasn’t been the most active offseason for the Toronto Raptors.

Sure, there’s been some movement on the Raptors’ front, but it hasn’t necessarily lit a fire under the team’s loyal fan base.

The departure of Fred VanVleet in free agency was a tough blow, but considering the price tag the Houston Rockets swooped in and grabbed him at, there wasn’t much of a chance Toronto was going to be able to compete with that offer, considering its cap constraints.

As a result, the Raptors have gone with the more conservative route, re-signing the free agent they could afford (Jakob Poeltl), watching Gary Trent Jr. opt into the final year of his contract and augmenting with a few cheap veteran pick-ups in Dennis Schroder and Garrett Temple.

There has been some excitement in the firing of Nick Nurse and the hiring of new coach Darko Rajakovic, in addition to the drafting of Kansas sharpshooter Gradey Dick, but overall it’s been a rather drab summer for the Raptors thus far.

But it doesn’t have to remain that way.

Portland Trail Blazers superstar point guard Damian Lillard has recently been loosely connected to the Raptors in a rumour.

There’s been widespread reporting that Lillard wants to be moved to the Miami Heat, and in this era of player empowerment, he’ll likely ultimately get his wish.

But it hasn’t happened yet, meaning there’s still a chance the Raptors – or any other team for that matter – could put together a package for the seven-time All-Star. Perhaps Toronto is the mystery team mentioned in another Lillard rumour from last week.

So, dare to dream. Here are three scenarios the Raptors could ponder should they be looking to acquire Lillard.

Give up on the future, go all-in on this season and maybe the next few

The framework of this deal is simple: the Raptors would acquire Lillard in exchange for a package that includes Scottie Barnes, Trent Jr. and other salary filler – Otto Porter Jr. and Thaddeus Young’s contracts would get the job done.

There would likely be draft picks that would need to go Portland’s way and the Raptors might ask for another cheap roster player from the Blazers, but that basic framework is what the deal would be.

The benefits for the Raptors are obvious. They would keep their two best players in Pascal Siakam and OG Anunoby, and allow those two guys to slide into more natural secondary and tertiary roles as scorers and leaders of the team.

Additionally, the loss of VanVleet would then probably not be felt at all, as far as pure basketball reasons go. VanVleet is a fine player, but he’s not the calibre of Lillard, who is among the league’s most prolific 3-point shooters, overall scorers and clutch performers. Lillard would be a significant upgrade at point guard for the Raptors over VanVleet.

The scenario for the Blazers also makes some sense because it would allow them to immediately add young talent without needing to draft again. Picks heading back from the Raptors would also be fairly important but the real prize would be acquiring Barnes.

Despite a tepid sophomore follow-up to a fabulous Rookie of the Year campaign, Barnes just turned 22 last week and remains as long and athletic as ever, blessed with remarkable vision and passing ability. That’s a good base to have surrounded by young gunners like Anfernee Simons, Shaedon Sharpe and Scoot Henderson.

This is the riskiest of the three scenarios outlined for the Raptors. Lillard is under contract until at least the 2025-26 season and has a player option for 2026-27. And while he’s a remarkable player, he’s also getting up there in age, and he’s owed a boatload of money over the next three seasons or so (think in the range of over $50 million per season on average). If things don’t work out with Lillard, having him under contract could destroy the Raptors’ cap situation for many years to come.

And this is to say nothing of if Barnes does take that next step. Leveraging the future to keep open the current competitive window would be quite the gamble.

Reset around Lillard

The basic premise behind this scenario has to do with reports that the Raptors have been shopping Siakam. With that in mind, this deal would essentially swap Siakam with Lillard as the team’s focal point.

Putting together such a trade would be relatively easy. In order to make the money work, the Raptors would just need to send Siakam and one of their veteran contracts (Porter or Young).

The dynamic of the Raptors as a team wouldn’t change much, and the club would probably get better because Lillard is a better player than Siakam. It would also unclog some of the positional bottleneck Barnes has with Siakam.

Toronto would look fairly imposing with essentially its entire team intact, but with Lillard leading the charge instead of Siakam.

From Portland’s point of view, however, such a deal doesn’t make a ton of sense. Trading a franchise icon like Lillard means the Blazers should be looking to hit the reset button, and acquiring Siakam wouldn’t do that.

The real kicker in the deal would probably have to be a draft-pick haul similar to what the Utah Jazz got from the Minnesota Timberwolves when they traded Rudy Gobert. That package is something the Raptors most certainly should not look to give up, even if it would be for Lillard.

Lillard the stopgap until the kids are ready

Lastly, this scenario would be all about using Lillard as a high-level vet/babysitter to help bring the Raptors' young players along.

In order to accomplish this, the structure of a deal would be for the Raptors to trade both Siakam and Anunoby.

The rationale behind doing such a move for the Raptors would be to help a young player like Barnes (and Dick) learn what it takes to be a professional while still picking up wins.

The current Raptors are likely bound for at least the play-in tournament, which is probably what adding Lillard without Siakam and Anunoby on the team would do as well. The benefit, however, would be to have a different veteran voice help shepherd along the Raptors’ youngsters.

The Blazers would still need picks from the Raptors because they’d be trading Lillard, but they probably wouldn’t be able to demand as much because they would be adding a piece in Anunoby that they’ve reportedly coveted for a while now.

At 26, Anunoby is a perfect young veteran who aligns with the Blazers’ timeline well enough and is seasoned enough to come in and act as a good mentor for Portland’s young core. Siakam, 29, still doesn’t line up that well, but he would be considered additional cost for the Blazers to pay to acquire Anunoby, allowing the Raptors to then free up Barnes under the watchful gaze of Lillard.