On September 27, 2023, the Portland Trail Blazers traded away fan favorite Damian Lillard to the Milwaukee Bucks. This trade was prompted by Bucks player Giannis Antetokounmpo, whose determination to win the 2024 NBA championship led to him pushing the Bucks management team to keep upgrading. This led to the Bucks announcing a three-team deal for Lillard, with the Bucks, the Suns, and the Blazers all trading players. 

The trade led to the Suns receiving Grayson Allen from the Bucks, and Keon Johnson, Nassir Little, and Jusuf Nurkic from the Blazers. The Blazers received Deandre Ayton and Toumani Camara from the Suns, and Jrue Holiday from the Bucks along with two 1st-round swaps with the Bucks (2028, 2030), and a 2029 1st-round pick. The Bucks received only Damian Lillard from the Blazers. 

Before the trade, the Bucks were a semi-relevant contender for the 2024 Championship. However, after the trade the Bucks have arguably become one of the top teams in the league. Pairing Antetokounmpo’s defensive capabilities with Lillard being one of the NBA’s best closers ever, the Bucks quickly became a top favorite to win the championship being ranked fourth, under the Boston Celtics, Phoenix Suns, and Denver Nuggets. 

After the trade, the Blazers had one of the league’s best, two-way guards—Jrue Holiday. The Blazers would waste little time with Holiday and began creating a deal to insure more assets.

The trade took place Sunday, October 1, where the Boston Celtics would receive Jrue Holiday in exchange for Malcolm Brogdon, Robert Williams, a First round pick from the Warriors, and a 2029 unprotected pick from the Celtics. 

The addition of Jrue Holiday to the Celtics easily makes the Celtics a top contender to win the championship this season. For the Portland Trail Blazers, this was a huge haul from the Damian Lillard trade with the Blazers earning: DeAndre Ayton, Robert Williams, Malcolm Brogdon, Warriors first-round pick, Celtics 2029 first-round pick unprotected, Bucks 2029 first-round pick unprotected, two pick swaps with the bucks (2028, 2030).

It’s expected that the Blazers will keep William and their new center Deandre Ayton, but more than likely they will trade Brogdon to add to their haul. While the loss of Lillard is heartbreaking for fans, the Blazers have begun building a new foundation to make up for the loss.