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The Damian Lillard sweepstakes aren't going full throttle just yet, but rumblings of dissatisfaction from the Portland Trail Blazers superstar have begun to surface. Lillard has not formally requested a trade or expressed his intent to part ways with Portland. Should that time come, though, nearly every team in the league would dial the Blazers' phone to acquire the six-time All-NBA point guard, including the Toronto Raptors.
The Raptors are just two years removed from winning their first NBA championship back in 2019. However, they had a rough 2020-21 season that saw them finish No. 12 in the East. Bringing in a superstar like Lillard could instantly help them return back to title contention. With that, the Raptors should try to take a swing at the Blazers to land the point guard.
So, what would Toronto's best package look like in a hypothetical trade for Damian Lillard?
Toronto Raptors acquire: Damian Lillard
Portland Trail Blazers acquire: OG Anunoby, Fred VanVleet, No. 4 overall pick, Toronto's 2022, 2024, 2026 first-round picks
Basically, Toronto would throw every attractive asset it has except for Pascal Siakam.
The draft gods gifted Toronto with the No. 4 overall pick in the upcoming 2021 NBA Draft. This should be the juiciest asset the Raptors can use to entice the Blazers into parting ways with Lillard. In addition, Toronto sends over a promising young wing in OG Anunoby, who showed massive strides with his game in the 2020-21 season. He averaged 15.9 points and 5.5 rebounds per game last year and shot 48.0 percent from the field and 39.8 percent from 3.
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Portland also acquires a proven winner in Fred VanVleet, who should be a steady backcourt partner with CJ McCollum if he sticks around. Finally, the Raptors send over a trio of future first-round picks and could also add pick swaps to sweeten the deal. Because of the Stepien Rule, this trade would have to be executed after that No. 4 selection is made this year.
Toronto would have a nice one-two punch with Damian Lillard and Pascal Siakam. The Raptors would also ideally like to retain All-Star veteran Kyle Lowry, whom they kept at the trade deadline this past March. While the fit with Lillard may be suspect due to their lack of size, Toronto has been running a small backcourt for the last couple of years anyway. Even at 35 years old, Lowry has proven to be an elite perimeter defender and should be able to cover Lillard's deficiencies on that end.
The 30-year-old superstar also reunites with Gary Trent Jr. in this trade, so this core would be one that head coach Nick Nurse can mix-and-match with during the postseason.
Raptors executive Masai Ujiri's track record has shown that he isn't afraid to swing big just as he did with the Kawhi Leonard trade in 2018. We all know how that turned out for the franchise, and it's likely that Ujiri is already closely monitoring Lillard's situation in Portland. Ujiri's contract is up this offseason, but that's a discussion for another day.
Nonetheless, it's highly likely Ujiri stays in Toronto. Assuming he does, it would be shocking if the Nigerian-Canadian doesn't get himself involved in trading for an increasingly disgruntled star like Lillard.
As of now, it seems like a long shot for the Raptors, and they would still have to fill out the roster to create a championship-caliber squad. Masai Ujiri has shown that he is capable of doing so. Getting the foundation superstar in Damian Lillard is a good way to start.
