Okay I do not know half of these so kind of stealing ideas based on posts above.
Danny Ainge: Cloud, I think he makes the right deal all the time, and it is not a bad thing, but he is always sure he is winning the trade. Unless he gifts me a player to make me feel better about myself. (Ebbs is a very close second)
Isiah Thomas: If its how Foreman said it would be me. I draft relatively well, but I have no idea how to piece together a winning team. I also then have to go to trusted GMs to see what I should do and I still mess it up. However, I always seem to hit in my picks even when its completely random and a player should not do that good.
Sam Hinkie: Donkey for his trust the process and just trading picks for more picks and more picks and then owning an entire draft.
Billy King: Daulten because he is bad.
Ted Stepien: Hank, If he could not own a draft pick, I am pretty sure he would be ecstatic about it. He trades it as much as he sells donuts.