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Pros and Cons of the Toronto Raptors pursuing Damian Lillard trade

Mike Luciano
Mike Luciano

Raptors Rapture

TORONTO, ON - JANUARY 08: Damian Lillard #0 of the Portland Trail Blazers drives to the net against O.G. Anunoby #3 of the Toronto Raptors (Photo by Cole Burston/Getty Images)

The Toronto Raptors were long thought of as an afterthought in the Damian Lillard trade sweepstakes, as the Portland Trail Blazers star seemed willing to do whatever it took to force his way onto the Miami Heat. The latest rumblings make it seem like the Raptors are going to give acquiring Lillard an honest shot.

The latest reports from Marc Spears hinted that an unknown Eastern Conference team was trying to grab Lillard before the Heat could secure his services. If Matt Moore of The Action Network is to be believed, it was none other than the Raptors who were poking around the Lillard market.

The Raptors should still be considered longshots in their pursuit of Lillard, as there are a lot of moving parts that could threaten to upend this deal. Having said that, Toronto owes it to their fanbase to at least consider getting Blazers executive Joe Cronin on the phone once again.

Toronto will need to figure out if all of the issues that come with bringing Lillard to town are worth it. If they figure out, in their mind, that Lillard could be a fit for this team, they should pull the trigger on bringing one of the best players in NBA history over to Canada.

Pros and Cons of Raptors trading for Damian Lillard

Pros

Players like Lillard don’t come on the market very often. Lillard can still challenge for 30 points per game every single night, as he is one of the best shooters in the league. Who better to fix one of the worst half-court offenses in the league than the Portland superstar?

While losing OG Anunoby (in all likelihood) and multiple first-round picks will likely be something Masai Ujiri doesn’t want to do, the possibility of acquiring such a game-changer without giving up either Scottie Barnes or Pascal Siakam represents a golden opportunity this front office can’t squander.

Damian Lillard could fit in with the Toronto Raptors.

Rather than risking the possibility of losing some of their core players in free agency and being left as a desolate wasteland around Scottie Barnes, adding Lillard would give them a contention window for multiple seasons, irrespective of which players end up bolting in 2024.

A starting five consisting of Lillard running the show at point guard, Barnes and Gary Trent Jr. as a pair of high-scoring wings, and a mighty frontcourt of Pascal Siakam and Jakob Poeltl would be enough to not only make the postseason but compete for a top-four spot regularly.

Toronto Raptors, Damian Lillard, NBA rumors
TORONTO, ON – JANUARY 08: Damian Lillard #0 of the Portland Trail Blazers drives to the net against O.G. Anunoby #3 of the Toronto Raptors (Photo by Cole Burston/Getty Images)

Cons

Lillard has all but said he only wants to play for the Heat, and the latest rumors seem to suggest that he would be willing to once again demand a trade if he isn’t sent to Miami. Would Toronto give away all of those assets just to call his bluff and see if he’s serious?

Lillard’s game might age well, but it’s fair to be worried about a 33-year-old guard who has a $121 million contract extension that hasn’t even kicked in yet. The financial flexibility Ujiri loves would be gone, as would large components of Darko Rajakovic’s bench.

Could the Toronto Raptors get burned by Damian Lillard?

Trading for Lillard would also make the future very uncertain for Pascal Siakam and Scottie Barnes. For Siakam, would he be willing to sign a long-term contract with a Raptors team that would likely pencil him in as the second fiddle for the end of his prime?

Barnes will also never be more than a tertiary option with Siakam or a secondary one without him. This marks a sharp philosophical change, as they would need to scrap their plans of a future led by Barnes to make sure that Lillard ends up in charge of this ship.

Damian Lillard, Toronto Raptors
TORONTO, ON – JANUARY 08: Damian Lillard #0 of the Portland Trail Blazers drives to the net against O.G. Anunoby #3 of the Toronto Raptors (Photo by Cole Burston/Getty Images)

Verdict

The Raptors need to consider going all-in on Lillard, provided that Barnes and Siakam are not going to be in the return package. If they can create an Anunoby-centric package, the Raptors could become a contender for years to come with Lillard at the tip of the spear.

While he is getting long in the tooth, his expert 3-point shooting should help his style of play age quite gracefully. Lillard is owed a ton of money in the next few years, which could make for some financially precarious decisions, but this is the best way to massively improve this team in a short span of time.

The Toronto Raptors could thrive with Damian Lillard.

The Raptors are not going to be a marquee free agent destination, and this core is likely not going to be bad enough to bottom out for top picks every single year. If fans want Ujiri to pick a direction, wouldn’t this be an emphatic declaration of his intentions with this team?

The risks are obvious, as a disgruntled, aging salary cap anchor could be enough to sink this team. Still, Ujiri has had success in the past with going all-in. Lillard’s pedigree and game-changing clutch shot-making would be enough to get the Raptors out of the doldrums and back on track.

Mike Luciano

Mike Luciano

Mike Luciano is an NFL staff writer for FanSided with a lifetime of expertise in all 32 teams, including the Las Vegas Raiders. He began his journey at Minute Media in 2020 and has since edited and written thousands of articles covering everything from the NFL Draft to the Super Bowl and free agency. Mike's work has been featured on Bleacher Report, Sports Illustrated, FanSided.com, and other outlets. Hot takes can be found on Twitter @ByMikeLuciano.