Why the Raptors should — or shouldn't — trade for Damian Lillard

With training camps right around the corner, the NBA's rumor mill is picking up steam again.

Despite his request for a trade back in July, superstar point guard Damian Lillard remains a Portland Trail Blazer. But the summer stalemate may soon be over.

According to Jake Fischer of Yahoo Sports, Media Day on Oct. 2 and the start of training camps on Oct. 3 loom as unofficial deadlines for Portland general manager Joe Cronin to trade his disgruntled star.

As the clock keeps ticking, the Miami Heat remain the most likely landing spot for Lillard, but Fischer noted another team could very well be in the mix.

“The [Toronto] Raptors are one of, if not the most viable threats to land Lillard outside of the Heat,” Fischer wrote.

NBA insider Marc Stein also stated several teams around the league believe the Raptors' interest is genuine.

The reports come as a bit of a surprise considering The Athletic’s Shams Charania recently suggested Lillard wouldn’t report if a team like Toronto were to trade for him, but this is the NBA, and strange things do happen.

In his report, Fischer outlined a three-team deal between the Blazers, Raptors and Phoenix Suns that would see the Suns send Deandre Ayton to Portland, with Phoenix landing Blazers big man Jusuf Nurkic and the Raptors acquiring Lillard, while also shipping OG Anunoby to the Blazers.

In order to make the deal work, there would surely have to be additional draft compensation involved. The Raptors would also need to offload more salary from their books (the combined contracts of players like Chris Boucher, Otto Porter Jr. and rookie Gradey Dick could work, as an example), but the groundwork of a possible deal is there.

As Fischer reported, one piece the Raptors wouldn’t include in any deal is Scottie Barnes, who they view as the building block of their future. Fischer also said there isn’t much interest from Portland in acquiring Pascal Siakam — despite his All-Star and All-NBA talents — because of his contract situation (he's entering the final year of his deal without an extension in hand).

So, using the base of the trade Fischer laid out, would trading for Lillard be worth it for the Raptors? Let’s take a closer look:

Why the Raptors should trade for Lillard

It’s a pretty simple reason why they should do it: He’s Damian Lillard, one of the greatest shooters and overall scorers to ever pick up a basketball.

And despite the rumor that Lillard wouldn’t report for camp if he were traded to a team like Toronto, there’s good reason to call the bluff.

Lillard is a stone-cold pro and takes his job very seriously. Do you really think he’s not going to show up for work just because he didn’t completely get his way? He isn’t James Harden.

Plus, from a pure basketball standpoint, the addition of Lillard would be a significant upgrade for the Raptors.

With the departure of All-Star point guard Fred VanVleet in free agency, the Raptors looked to have a major void at the position – even with the acquisition of FIBA World Cup MVP Dennis Schroder. Bringing in Lillard suddenly turns a definitive offseason loss for the Raptors into a big win, as Lillard is a certifiable upgrade over VanVleet.

The loss of Anunoby would hurt, but a scenario that sees Toronto keep the 22-year-old Barnes and allows Lillard to team up with Siakam means this is a team that could rapidly return to contender status.

Considering the way rookie-scale deals normally work, it’s safe to assume Barnes will be around for at least another six years. Including this season, Lillard will be under control for the next three campaigns at minimum, with a contract extension kicking in at the start of 2025-26. Siakam still has to work out a new deal, but his contract could be set up to align with Lillard’s timeline.

This would give the Raptors multiple kicks at the can with two All-NBA talents, with Barnes continuing to develop into what the team hopes will be an All-Star contributor.

Additionally, similar to when Toronto made the move for Kawhi Leonard, there wouldn’t be any confusion about who the No. 1 guy on the team is. It would be Lillard, something every player — including Siakam and Barnes — would understand given the Portland star’s stature and standing in the game, to say nothing of his prolific body of work.

To put it simply, if the Raptors are serious about being immediate contenders again, then acquiring Lillard would be the best way to do so.

Why the Raptors shouldn’t trade for Lillard

If you’re of the mindset that the Raptors need to pull back and look to rebuild, then the reasons against trading for Lillard are already apparent to you.

From a timeline perspective, the acquisition of Lillard just doesn’t make sense.

Despite his immense talent, Lillard is also 33 years old. Yes, his shooting ability and work ethic will mitigate some of the effects of Father Time, but unless the Raptors do win it all, Lillard's price tag would be astronomical – and we aren’t even talking about Anunoby or the possibility that they might have to trade 2023 first-round pick Dick, either.

No, the real devastating factor in making a move for Lillard would be the amount of draft capital the Raptors would likely have to surrender in a deal. Every team can now thank the Minnesota Timberwolves for setting the bar for what teams are looking for in exchange for an All-Star player after last summer's Rudy Gobert blockbuster.

The amount of draft capital the Raptors would need to give up just wouldn’t be worth it.

You also have to consider the kind of money Lillard is slated to make on his upcoming extension – think an annual average salary of more than $60 million per year. Such an exorbitant salary, in addition to whatever number Barnes’ and Siakam’s next contracts will come in at, could completely destroy Toronto’s cap situation over the next three to five seasons.

Again, unless the Raptors win it all, being stuck with massive salaries tied up in just a few players and little to no draft capital could be absolutely calamitous for the franchise.

And here’s one more thing: "Winning it all" doesn’t look nearly as likely as when Toronto made the move for Leonard in the summer of 2018. For one, that Raptors team had a lot of more depth around the edges of the roster, with the likes of VanVleet, Siakam and Norman Powell making up one of the deadliest bench units in the league. Plus, the Eastern Conference wasn’t nearly as talented back then as it appears to be now.

Realistically, even with Lillard on the team, are the Raptors really that much better than the likes of the Boston Celtics, Milwaukee Bucks and Heat? Even teams like the Cleveland Cavaliers and Philadelphia 76ers – despite all the drama happening there – could still be better than the Raptors with Lillard, Siakam, Barnes and thin depth around them.

Making the big, splashy trade for Lillard just looks like too risky of a gambit.