Franz Wagner
The Magic are another young team that's quickly risen from an afterthought to a playoff contender. Orlando doesn't have a chance to win a championship this year like Oklahoma City does, but it has a young core already in place and a future superstar in Paolo Banchero.
What the Magic need more than anything is a guard who can facilitate and provide another scoring option, whether it's getting isolation buckets or spotting up from three.
Enter Simons, who would be a perfect yin to Banchero's yang.
To get Portland to part ways with its best young player, though, Orlando would have to give up something special in return. In a perfect world, that would be Wagner, a versatile 6-10 22-year-old.
Wagner was the No. 8 pick in the 2021 draft and has statistically improved every season he's been in the league. This year, he's posting averages of 20.9 points, 5.9 rebounds and 3.9 assists, and his dip in shooting percentages seems to be an aberration. He had shooting splits of 49/36/84 in 80 starts last year.
A trio of Henderson, Sharpe and Wagner would bring balance to Portland's roster, and there's an argument to be made that Franz would be even better playing with the ball in his hands more often as a lead facilitator rather than playing off Banchero.