2. Closes contention window
Damian Lillard turns 33 years old next month, and there is no way to tell how many years he has left at the top of his game. Will he still be one of the best players in the league at 38 like LeBron is right now? Even King James admitted that his production is starting to fall off.
Lillard has already shown some cracks by missing games in the last four years. He wants to win now because even he is not sure how many years of greatness he has left.
If they trade the third pick for another player in his 30s, Portland has three to five years to make noise before being forced to retool. That gets shorter if Lillard starts declining quicker.
Even trading for a 25-year-old star rushes the window and puts more pressure on now. It will be a fringe All-Star meaning that player will likely quickly decline into a role player in their early 30s.
Keeping the third pick opens Portland’s contention window for the next decade. Even as Lillard ages, Shaedon Sharpe, Anfernee Simons, and the latest pick should be ready to take over and lead another run of success in Portland. Re-signing Jerami Grant helps push the window wide open, but that rests on the third pick becoming a star.