Oladipo isn't an immediate upgrade over Matthews, but his ceiling is much higher and plays with relentless energy. If you look up "motor" in the dictionary it will give you picture of Oladipo. So, lets get him.
Step one: Trade Matthews (7.2) + 10 (1.9) to Phoenix for Gortat (7.7) + 5 (2.8) + Beasley (5.8)
Why Portland does this: We get a good center in his prime for good value, and (already fan favorite) Victor Oladipo. Unfortunately we have to take on the oversized contract of Beasley.
Why Phoenix does this: They unload a lot of cap space, and move down just 5 spots in a draft with lots of talented bigs in that areas. They get rid of notorious ball-hog and cap-eater Michael Beasley.
Portland goes from having 13.5 million (before the pick is signed) to 8.5 million. The 5th pick takes up 2.8 mil, so we have 5.7 million left to spend.
Step two: draft Victor Oladipo. Duh.
Step three: Sign Gerald Henderson for 2x6. He is an underrated player. Good ball handler and average shooter. Solid defender.
Step four: Sign Ivan Johnson to the minimum and trade Michael Beasleys bum a** to some team along with a second rounder and cash at the deadline if he doesn't play well.
We would for sure be the best offensive team in the league with a potentially good defense, provided that Lillard improved his defense over the summer, Oladipo can immediately step in and provide a strong defensive intensity, and that Gortat provides adequate rim protection.