There have been many rumors that Damian Lillard might leave the Trail Blazers, and that the front office and Dame will have serious conversations about his future with the Trail Blazers. Dame could leave under one condition, if the team wants to trade him. Damian Lillard probably would not leave if he chooses since he is very loyal to the Blazers, like nothing we have seen in the modern era.
Trade Destinations
If Dame and the Trail Blazers agree for him to be traded, here are some landing spots for Damian Lillard:
New York Knicks
The Knicks are always monitoring for any stars that would be traded, and they could try to get Dame. The Knicks have a ton of assets, including 11 future picks, in which they could trade 8, and many young players like Immanuel Quickley, Quentin Grimes, Obi Toppin, RJ Barrett, and more. These players plus picks can entice the Blazers to send him to the Knicks. The Knicks then would have a big three of Julius Randle, Dame, and Jalen Brunson. Although the fit with Brunson and Dame is not as good defensively from them being two small guards, their offense would be insane.
Miami Heat
Pat Riley has always been known to make many blockbuster trades, and Damian Lillard fits their PG hole. Dame would be amazing for the Heat since he can give them another star to pair with Jimmy Butler. A trade to get Damian Lillard for the Heat would involve Tyler Herro, Duncan Robinson, some other players and picks. The Blazers could like this package because they get Tyler Herro, who has shown he could be a great player offensively, and Duncan Robinson was a starter level player who could resurrect his career.
Boston Celtics
Now this is a little hard to think about but if Jaylen Brown wants a trade, this actually might happen. Jaylen Brown would be a young star that the Blazers would want if Dame gets traded. Jaylen along with a few picks and salary filler could get it done for this trade. Dame would fit in decently with the Celtics, and there are not many players better than Dame to get if Jaylen Brown wants out of Boston.
Others Potential Destinations
The Pelicans have many young players and picks to trade for Dame. The Philadelphia 76ers can trade for Damian Lillard if the James Harden experiment does not work. The Minnesota Timberwolves and Memphis Grizzlies have great young talent and picks, and they both want to contend.