Jude Magnotti ‘26
EE Sports Columnist
Impossible”…these were the first words of every Trail Blazer fan alive when on Thursday September 28th, after 3 straight months of endless trade drama, franchise icon Damian Lillard was traded to the Milwaukee Bucks.
However, before we can even begin to break down this trade, we must retrace how we got here. On July 1st 2023, Damian Lillard officially requested a trade out of the Portland Trail Blazers. Lillard was drafted by the Blazers 6th overall in the 2012 and went on to become the all time leading scorer for the franchise. Lillard was just coming off a season in which he put up the best statistical numbers of his career averaging 32.2 points and 7.3 assists a game. However, despite Lillard’s individual success the Blazers only won 33 games and finished 13th in the west.
Entering this season at age 33, Lillard knew that he was running out of time to win a championship in Portland. As a result, he gave the Blazers a choice. Trade the number 3 overall pick for a player who could help the team, or keep it and trade him to another team.
The Blazers ultimately decided to draft Scoot Henderson 3rd overall and, as promised, Lillard demanded a trade a week later. However, Lillard demanded to be traded to one team and one team only: the Miami Heat. Reports indicated that the Blazers and Heat were involved in trade talks, but it seemed like every week another report would come out that they were unable to find a middle ground.
The Heat were offering Tyler Herro and multiple picks, but the Blazers were not going to trade their franchise icon for nothing and they demanded more. Despite Dame wanting Miami and Miami wanting Dame, the Damian Lillard trade saga was stuck on repeat for months on end.
Reports would indicate that the discussion was gaining traction just for ESPN’s NBA insider Adrian “Woj” Wojnarowski to come out and give a “BIG ” update that there was no deal close to being done. Little did the world know while everyone was focusing on Miami, there was another team lurking in the shadows waiting to pounce–the Milwaukee Bucks.
Milwaukee had been floated around as a possible destination early on, but was little more than an afterthought at this point in the process. People believed that the Bucks simply did not have the assets to pull off a trade for a player of Damian Lillard’s caliber. However, out of completely nowhere the Bucks came in and stole Lillard away from Miami. In a three team trade involving the Bucks, Blazers, and Suns, Damian Lillard was traded to the Bucks in exchange for Deandre Ayton, Jrue Holiday, and a first round pick.
Not only did this deal come as a shock to the sports world, it came as a shock to Blazers fans seeing how little they got for Lillard. Luckily for them, Joe Croinin and the Blazers front office had been playing another angle the entire time. Only a few days after the Dame trade, Portland traded Jrue Holiday to the Boston Celtics for Robert Williams, Malcolm Brodgen, and two first round picks. More than they got for Dame!
People suddenly went from claiming that the Blazers had been fleeced, to believing that they had made the best trade of the off-season. With the Holiday trade done, the Damian Lillard trade saga was officially over for Portland. Three months of endless torture and pain had all culminated in a 4-team mega trade that permanently changed the championship odds of multiple contending teams.
Starting with the Bucks side of the story: they walked away with the ultimate prize of this trade: Damian Lillard. The Bucks already have a superstar (and arguably the best player in the league) in Giannis Antetokounmpo. Now that he is paired with his best teammate ever in Damian Lillard, the two are sure to form one of the most formidable duos in the league.
Over in Boston, the Celtics were able to perfectly fill the void left by the departure of Marcus Smart. However, it is important to note that even though they acquired a valuable piece in Jrue Holiday, they gave up a king’s ransom for him. They gave up one of their best frontcourt players in Rob Williams along with sixth man of the year, Malcolm Brodgen. There is no question the Celtics have a formidable starting five, but all it takes is one injury to Kristaps Porzingis and the Celtics have nobody to play in the frontcourt off the bench besides a 37 year old Al Horford. This could prove deadly to the Celtics in the long run, but at least for now the Celtics have put themselves in an excellent position to make another finals run.
Next, heading to Phoenix, the Suns were able to address by far their team’s biggest weakness: depth. The Suns had an elite starting five including stars like Devin Booker and Kevin Durant, but they lacked any support off the bench. In this trade, the Suns were able to get off Deandre Ayton’s contract while also adding valuable bench pieces in Jusuf Nurkic, Grayson Allen, Keon Johnson, and Nassir Little. They received a starting center in Nurkic, two dynamic guards in Johnson and Allen, along with an extremely versatile forward in Nassir Little. If the Sun’s super team was not bad enough, they have only fortified their roster further and are heavy favorites to make it out the west.
Finally, we have the team that was the focal point for this entire trade: The Blazers. If you had asked me what I would grade the trade when the Blazers first made it, I would have said D+ at the best. However, after the incredible Jrue Holiday trade I’m switching the grade to A+.
Not only were the Blazers able to trade Dame to a contending team, they got an absolute haul in the end. They got a former number 1 overall pick with a lot of potential in Deandre Ayton to form a dynamic pick and roll duo with Scoot Henderson. In addition to this, they got a young talented rim protector in Rob Williams to cover up Anfrenee’s and Shaedon’s defensive weaknesses.
In addition to that, they got an excellent sixth man and veteran in Malcolm Brodgen who can mentor the young players on the team through their first season. They also got three unprotected firsts! The Blazers took a 33 year old point guard and turned him into 5 different valuable assets that will help build a future for the Blazers. Scoot Henderson is in the best position he could possibly be in right now. He has full control of a decent team along with an organization that fully trusts him and his skillset. This trade was the final step into fully moving on from the disappointing Damian Lillard era, to putting the future of the blazers in the hands of one man: Scoot. Henderson.