8. Khris Middleton - 2012
Trail Blazers pick: Will Barton, No. 40
Other pick: Khris Middleton, No. 39 (Detroit Pistons)
As far as No. 40 overall picks go, Will Barton was a solid selection for Portland. Unfortunately, he didn't peak until he left the Trail Blazers to go to the Denver Nuggets, where he went on to win two Six Man of the Year awards as a microwave scorer who provided tremendous energy off the bench. It would have been nice to have Khris Middleton instead.
Like DeAndre Jordan, Middleton is another underrated star. He started his NBA career underutilized in Detroit before eventually being traded to the Milwaukee Bucks. He was an essential part of the Bucks' 2021 championship run over the Phoenix Suns and even had a career-high 40-point outing in Game 4.
To go along with his Finals ring, Middleton is also a three-time NBA All-Star. In his career, he's averaged 16.9 points, 4.8 rebounds, and 3.9 assists on efficient 46/39/88 shooting splits. Middleton is an underrated star because he isn't necessarily flashy; he makes the right reads and rarely tries to force anything.
Middleton is an ideal complementary star because of his elite shooting and ability to play within the game's flow. He knows his role as a sidekick and plays it to perfection, as evidenced in the 2021 Finals. As a 6-foot-7 sharpshooting wing, Middleton is another piece that would have fit in seamlessly with Damian Lillard, who was selected No. 6 overall in the same draft class.