Everyone knew the move was coming: The Portland Trail Blazers would trade Damian Lillard and reset the franchise. The only question was when and to where. Would general manager Joe Cronin finally relent and accept the Miami Heat's offer? Were there even other offers on the table?
The drama lingered through the summer and almost into October before the Milwaukee Bucks shocked the NBA world and swooped in to acquire Lillard, pairing him with Giannis Antetokounmpo and resetting their own franchise to make another title run. Included in the three-team deal was Jrue Holiday, who had no place in Rip City as a veteran star looking to win another title himself.
The Trail Blazers set themselves up for a part two of the Lillard trade
Not only did Cronin hold out and land a much better Milwaukee package instead of caving and accepting a sub-par Miami bundle, he made the smart move to grab a two-time All-Star and NBA champion point guard. He could flip Holiday to a contender, piggybacking the offseason's biggest trade with a second massive deal for another haul of assets.
Portland received Deandre Ayton, Toumani Camara, an unprotected 2029 Bucks pick and two Milwaukee pick swaps for Lillard. Now the Blazers had a five-time all-defensive team floor general and Olympic Gold Medalist to sell as well.