According to Chris Haynes, Dame will be getting the supermax this summer, meaning he is locked in until he is 34 years old. This is all-in or nothing time for Portland. If they take a win now approach, I think the moves below will make Portland a serious contender.
http://www.espn.com/nba/tradeMachine?tradeId=y6epgf6n
CJ McCollum/Gary Trent Jr to NOP for Jrue Holiday: Holiday is not as an explosive scorer as CJ, but his defensive superiority is much needed in the backcourt. Having Dame and CJ as the defensive liabilities makes it extremely difficult to be an elite defensive team.
http://www.espn.com/nba/tradeMachine?tradeId=yyjxncyh
Evan Turner/Mo Harklesss/2019 1st round pick to DET for Blake Griffin: This is a risky move with Blake's injury history, but he could be had for relatively low value. Detroit has been rumored to want to move on from Blake and enter full rebuild. Turner and Mo will be on the last year of their contracts and will allow DET to start the rebuild.
http://www.espn.com/nba/tradeMachine?tradeId=y6q53nhp
Meyers Leonard to MIN for Robert Covington: Covington would help at SF as he is a prototypical 3 and D player.