Is Damian Lillard the right fit and are they ready to pay the cost to acquire him? Lillard is likely to make a huge comeback including more first-round picks and prospects.
The big question before building any kind of Knicks trade for Lillard is whether or not they give up Jalen Brunson. He is now unequivocally their best player and best signing in the Leon Rose era, who also holds the same position as Lillard. Send Brunson in a trade and you have fewer prospects and you pick the gap to close, and you also free up the point guard position for Lillard.
Keep it and you’ll have to figure out how to play the two together. Lillard is the better player and would probably be given lead ball handling duties. Brunson could fit well as a second option and offensive threat off the ball, but he and Lillard would make a terrible defensive pairing in the backcourt. However, if you are trading for Lillard it is to add him to an already competitive squad and sending Brunson limits your potential return. The Knicks should just try to figure that out.