James Plorde

Damian Lillard in his new Bucks uniform

For years, seven-time NBA All-Star Damian Lillard was loyal to the Portland Trail Blazers. Drafted by them in 2012, he stuck with them even though they had completely failed to build around him. The farthest they got in the NBA playoffs was the Western Conference Finals, where they were swept by the Golden State Warriors; a team that successfully built around their star players and has won four championships as a result.

In what some Trail Blazers fans would call betrayal, and after more than 10 years of very little success, Lillard requested a trade in July 2023, specifically to the Miami Heat. The following months came and went with drama surrounding the request of the Heat, and other teams popped up as candidates, such as the Toronto Raptors. 

In the afternoon of Sept. 27, 2023, Adrian Wojnarowski posted on X (formerly known as Twitter) one of his signature “Woj Bombs,” where the NBA insider releases breaking news about the league. 

The news that came out was that Damian Lillard was traded to the Milwaukee Bucks in a three-team trade involving his team, the Portland Trailblazers and the Phoenix Suns. The Suns received Jusuf Nurkic, Grayson Allen, Nassir Little and Keon Johnson. The Trail Blazers received Jrue Holiday (who was later traded to the Celtics), Deandre Ayton, Toumani Camara and the Bucks’ 2029 first-round draft pick, along with swap rights for the Bucks’ first-round picks in 2028 and 2030. The newly formed partnership of Lillard and two-time NBA MVP and NBA champion Giannis Antetokounmpo propelled the Bucks to the title favorites, according to BetMGM.

The trade followed several cryptic comments by Antetokounmpo about wanting to play somewhere other than Milwaukee. The Bucks had gone all the way in 2021, winning the NBA championship. But they had failed to even reach the Eastern Conference Finals in 2022, and in 2023 losing in the first round of the playoffs. Although this move definitely makes sense, some part of it definitely comes as a way to keep Antetokounmpo in Milwaukee, as he has never had a genuine superstar on his team. He has had three-time All-Star Khris Middleton by his side for his whole career, who came up huge in the Bucks’ championship run, although no one in the NBA community considers him a true star player.

The trio of Antetokounmpo, Lillard and Middleton will certainly contribute a lot on offense, with a combined points per game of 78.4 last year. Losing Jrue Holiday will definitely hurt, though, as the combination of him and Brook Lopez was the defensive rock of the Bucks. The trade is essentially trading defense for a lot more offense, and, as the popular saying goes, the best defense is sometimes more offense. 

Despite this, the “superteam” approach to building winning and lasting dynasties in the NBA hasn’t worked recently. The best examples of this were the Brooklyn Nets, who had superstars Kevin Durant, Kyrie Irving and James Harden and ended up being beaten by the Bucks in their path to their championship in 2021, this being the farthest they ever got. The opposite of this team-building philosophy has won teams championships, like this past year with the Denver Nuggets, who developed the players that they drafted, Jamal Murray and Nikola Jokić, into stars. On paper, Lillard and Antetokounmpo seem like they would work out great, although history has shown that the best teams on paper do not always win championships.