3. Portland drafts a foundational star
Suppose the No. 1 and No. 2 events come to fruition. Simons is traded, and Lillard feels his time with the Bucks is up, either because they have continuously come up short in the playoffs or because he finished the mission by securing a championship.
The next step in the process should be for Lillard to evaluate his options and potential landing spots outside of Milwaukee. Portland would be extremely high on Lillard's list, but perhaps a team like the Miami Heat, his preferred trade destination over Milwaukee, also intrigues him. The Blazers must sell their roster to Lillard, especially if he still doesn't have a championship on his resume.
Lillard could decide he wants to return to Portland regardless because he views it as home. But the Blazers would make a much more compelling case if they had a foundational star like Duke's Cooper Flagg to build around.
It's reminiscent of when LeBron James returned to the Cavaliers after his stint in Miami, to a lesser extent. The Blazers need to find their Kyrie Irving, whether that's Scoot, Sharpe, or another draft pick like Flagg. Then, they can trade their next pick for more established talent when Lillard returns, similar to how the Cavs traded the No. 1 overall pick (Andrew Wiggins) to the Timberwolves for Kevin Love.