5. Trading Damian Lillard
Sending away their long-time franchise point guard was a bitter moment for the Blazers – but it ended up becoming bittersweet when the entire return, including the Holiday trade, was announced.
The Phoenix Suns were part of the three-team deal that landed Lillard in Milwaukee. Portland sent Jusuf Nurkic to Phoenix and received Deandre Ayton in return. That’s an immediate upgrade at a position the Blazers have struggled with the past few seasons. Ayton fits into the franchise’s rebuilding timeline at 25 years old.
Portland also grabbed a 2029 unprotected first-round pick from Milwaukee, who will face similar questions as Boston based on the futures of Lillard, Giannis Antetokounmpo, Brook Lopez and Khris Middleton. The Blazers picked up potential pick swaps from the Bucks in 2028 and 2030, as well.
The deal looks even better now than it did when it originally went down as overlooked toss-in Toumani Camara is developing into a legitimate rotation player for Portland.