This is from a facebook group question, not including the author because he might not want me to. (This is the group if you want to join.)

Evaluating whether trading Trae Young for Damian Lillard would be a good deal for the Milwaukee Bucks requires looking at several factors: the players’ current performance, their fit with the team, their contracts, and the Bucks’ overall goals. Let’s break it down based on what we know as of March 11, 2025.
Current Performance
Trae Young, at 26 years old, is in the prime of his career. This season (2024-25), he’s averaging around 22 points and 11 assists per game, though his efficiency has dipped slightly compared to his peak years. He’s a dynamic offensive player, elite at creating his own shot and setting up teammates, but his defence remains a weak point—opponents often target him in pick-and-roll situations. As they do Dame of course.
Damian Lillard, now 34, is still a high-level performer but showing signs of decline. In his second season with the Bucks, he’s averaging about 25 points and 7 assists, though his efficiency from three (around 35%) is down from his Portland peak (37-39%). His playoff experience and clutch scoring are invaluable, but his defensive limitations are similar to Young’s, and his age suggests a shorter window of elite play.
Fit with the Bucks
The Bucks’ core revolves around Giannis Antetokounmpo, a two-time MVP who thrives with the ball in his hands and needs spacing around him. Lillard’s off-ball shooting (even with a slight dip) complements Giannis well, as he can stretch the floor and hit deep threes, drawing defenders away from the paint. Their pick-and-roll game has also started to gel better in 2024-25 after a rocky first year together. Here my analysis of what still doesn’t click with Dame in detail.
Trae Young, on the other hand, is more ball-dominant. His playstyle—high pick-and-roll usage and creating out of dribble-heavy sets—could overlap with Giannis’ need to attack the basket. Young’s three-point shooting (around 36-38% career) is solid but not as lethal from deep as Lillard’s, which might clog the floor more for Giannis. Defensively, swapping Lillard for Young is a wash at best; neither is a stopper, and the Bucks already struggle to hide one guard defensively alongside Giannis and Brook Lopez. Would Trae be able to put aside his ego with Giannis on the floor having the ball more than him? I doubt it!
Contracts
Lillard’s contract is massive: he’s owed $48.8 million this year, $54 million in 2025-26, and has a $63.2 million player option for 2026-27. That’s a lot of money for a player who’ll be 36 by the end of it, especially if his production continues to taper off.
Young’s deal is more team-friendly: $43 million this year, $46 million in 2025-26, and a $48.9 million player option for 2026-27. He’s eight years younger, so his contract aligns better with long-term planning, though it’s still a hefty commitment.
Bucks’ Goals
The Bucks are in win-now mode with Giannis, who’s 30 and under contract through 2027-28 (with a player option). After winning the title in 2021, they’ve been all-in on maximizing his prime, as seen with the Lillard trade in 2023. Trading Lillard for Young could signal a slight pivot—still competing now but also eyeing a longer contention window. However, Young’s playoff track record (one Eastern Conference Finals run in 2021) doesn’t match Lillard’s veteran savvy, and the Bucks might sacrifice some immediate title equity.
Pros and Cons for the Bucks
Pros of Getting Trae Young:
- Younger, potentially extending the Bucks’ contention window past Lillard’s decline.
- Elite playmaking could boost role players like Khris Middleton (if he stays healthy) and Bobby Portis.
- Slightly cheaper contract with more years of prime production.
Cons of Losing Lillard:
- Lillard’s playoff experience and clutch scoring are proven; Young’s postseason resume is thinner.
- Chemistry with Giannis is improving—why disrupt it for a less certain fit?
- Young’s ball dominance might limit Giannis’ touches, reducing his effectiveness.
Verdict
For the Bucks, trading Lillard for Young straight up isn’t a clear upgrade. Lillard’s fit with Giannis, despite early struggles, is starting to work, and his experience aligns with their urgent title push. Young’s youth is appealing, but his style might not mesh as cleanly, and the defensive issues wouldn’t improve. Unless the Bucks are worried about Lillard’s age catching up fast—or they’re getting additional assets (e.g., picks or a defensive wing)—keeping Lillard makes more sense for their current timeline. A straight swap feels like a lateral move with too much risk for a team that’s already pot-committed to winning now. The biggest problem is that no superstar wants to play with Giannis. No matter who is on the Bucks with him sooner or later gets blamed for everything. So no, Trae for Dame would only happen if Trae was really really desperate to leave his current team.