Toronto Raptors Receive: G Damian Lillard
Portland Trail Blazers Receive: G Fred VanVleet, F OG Anunoby, G Malachi Flynn, No. 4 pick, 2023 First-Round Pick, 2025 First-Round Pick
This would be a monster trade to pull off this offseason. The landscape of the NBA would change drastically, as the Toronto Raptors would be going for it again as contenders in the Eastern Conference.
The Portland Trail Blazers many assumed would be rebuilding if they ever traded away Damian Lillard, but this haul would give them a chance to remain competitive.
Fred VanVleet and C.J. McCollum would form a strong backcourt duo. While not the scoring threat that Lillard is, VanVleet can fill it up in his own right and brings a little more defense to a team that struggled to slow down anyone last season.
OG Anunoby is a legitimate two-way building block on the wing. Portland has tried for years to find a wing to complement their strong backcourt and Anunoby would provide that. He is a great defender and has developed nicely on offense. Malachi Flynn is another young player that would give Portland the backup point guard they have lacked as well.
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The crown jewel of this trade package is the No. 4 overall selection. Portland could use that to add an impact rookie to their roster to build the foundation for the future. The future first-round picks give them plenty of flexibility when it comes to rounding out the rest of their roster.
Portland can build the old-fashioned way through the draft or circumvent the process and land an established veteran if they feel the roster is strong enough to compete.