Damian Lillard, Milwaukee Bucks
There's still plenty of season that needs to be played out this year and the Milwaukee Bucks haven't been the disaster that they were through the first month of the year of late, but if this team does have another disappointing end to the year, it's only natural to think about what types of moves could end up transpiring during the offseason. This could be considered a bold prediction, but I believe there's at least an outside shot that the Bucks could end up trading Damian Lillard after this season.
If the Bucks do lose in the first or second round of the NBA Playoffs again, there's going to need to be a big move made by the team. Looking at their roster, there's a chance that they may have to explore a blockbuster move around Lillard. It's unlikely the team will be able to trade Khris Middleton and I can't imagine the Bucks will want to trade Giannis Antetokounmpo. That leaves trading Lillard as the most likely path the Bucks can take to retool the core around Giannis.
Brandon Ingram, New Orleans Pelicans
Since it was revealed that the New Orleans Pelicans and Brandon Ingram were not going to be able to settle on a contract extension, it became a matter of "when" and not "if" a trade would take place. At least thus far, it doesn't appear as if the Pelicans had pushed hard to get a deal done. However, with the Pelicans in the midst of a lost season and the two sides not reportedly any closer to a contract extension, it would appear as if a trade is becoming more and more of a realistic possibility heading into the NBA Trade Deadline season.
Because of those circumstances, I predict that we're going to see a trade of Ingram probably sooner rather than later in 2025. It'll be interesting to see what the ultimate deal looks like but at this point, especially with how this season has transpired for New Orleans, I believe Ingram is going to be on a new team at some point soon. It makes the most sense for a team that has continued to struggle with its identity.