Damian Lillard
If the Toronto Raptors go all-in on retooling and competing next season, there aren’t many better trade targets than Damian Lillard. While he has not yet formally requested a trade from the Portland Trail Blazers, the Raptors should aggressively pursue Lillard this offseason.
Lillard would give the Raptors a bonafide star to help push them back into contention in the Eastern Conference. His elite scoring and great playmaking would give Toronto a chance at having one of the best offenses in the NBA.
In any deal for Damian Lillard, draft compensation will be key. It won’t get much better than a fourth overall pick for the Trail Blazers and Toronto has all of their future first-round picks at their disposal as well. They could throw in at least one or two more to get Portland to consider a trade.
The Raptors could offer Fred VanVleet, OG Anunoby and Malachi Flynn to match salaries, giving Portland a solid haul to start their rebuild with. Acquiring those players, with what they already have in place, could make them playoff contenders in the Western Conference still.
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Toronto would be able to fill out their roster and make their push as contenders in the Eastern Conference with a new face of the franchise in Damian Lillard.