Damian Lillard Trade Rumors: Raptors Making Progress for Blazers Star; Magic Linked

The Toronto Raptors have been one of the surprising teams linked with a potential trade for Damian Lillard over the last week or so. Don't expect that buzz to die down.

According to Sportsnet's Michael Grange, the Raptors are "very much in the mix. Certainly not all the way there and likely not even halfway to getting a deal done, but progress has been made."

He continued:

"By all accounts, the Raptors seem at least reasonably confident they can maneuver their way to the front of the line, past the Miami Heat—Lillard's preferred destination—and ahead of a team such as the Brooklyn Nets, who have the draft picks to get something done if Portland is open to taking on the last two years of Ben Simmons' contract. The Orlando Magic could also make themselves heard, per sources."

The Raptors could build a deal around OG Anunoby, a slew of draft picks and swaps and other considerations for Lillard. That would give the Raptors and strong core of Lillard, Pascal Siakam and Scottie Barnes, and could perhaps help convince a former target of the team—two-time MVP Giannis Antetokounmpo—to consider signing with them if he becomes a free agent in two summers.

Whether Lillard would have any interest in playing for Toronto is another matter entirely. Most reporting suggests it's Miami or bust for the star point guard, at least from a preference perspective, with some reports indicating he'd still request a trade to the Heat even if he was dealt elsewhere this offseason.

The issue for Miami is that teams like the Raptors can offer vastly superior trade packages. That has significantly altered their leverage in trade talks despite Lillard's preferences being known.

But there is also a question for Toronto—what is the end game in a potential Lillard deal?

It's hard to imagine the Raptors becoming favorites for the title with a core of Lillard, Siakam and Barnes. That's a very good team, no doubt, but is it going to be better than Antetokounmpo's Bucks or the Boston Celtics, let alone top teams in the Western Conference like the defending champion Denver Nuggets?

Probably not.

So is it really worth risking all of those assets and potentially young players for an outside shot at contention? All while adding the 33-year-old Lillard, who is scheduled to make $176.2 million over the next four seasons, culminating in a gargantuan $63.2 million in the 2026-27 season?

The only way the answer should be yes is if the Raptors believe they have a legitimate shot at attracting another star—potentially Antetokounmpo in two years—to join Lillard.

The Raptors might counter that their last blockbuster deal, acquiring Kawhi Leonard, worked out quite well. And while Lillard may be a bonafide star, he isn't the two-way force that Leonard was during that stage of his career.

It's legitimately questionable whether Lillard can lead a team to a title without having another superstar next to him. And it's why teams like the Raptors and Magic need to decide whether taking a major jump forward in their respective timelines, at the expense of young players and draft assets, makes more sense than a patient rebuilding approach.

If either decides it makes sense, however, it's very bad news for a Heat team that won't be able to trump the best offers teams like the Raptors, Magic or Nets can make.