I don't even have to know what the 'stats' are on trades between those two GM's to know that's a dumb take...sorry
What Whitsitt knew is that you can't change the trajectory of a team by fucking around with the back end of the rotation. Dinking with the 8th or 10th or 12th players on the depth chart isn't going to add any playoff wins. Whitsitt worked the top part of the rotation and was always searching for elite talent while knowing the price was going to be significant. He didn't get irrationally attached to average players, and he wasn't stupid enough to believe that sifting thru dumpsters was going to make any difference
but these 'back-end-low-level-bargain-basement-dumpster-diving-pray-for-nuggets' trades are Olshey's only comfort zone when dealing with other GM's. He seems to be a chickenshit about entering into any discussions when he has to actually deal in a true give-to-get ratio. It's just so much easier for him to create an untouchable list and that way, not take any risks. And, the one asset he had for most of those discount trades was cap-space, which he pissed away in 2016.
Olshey had been on the job for 6 fucking years last April...6 years. And in that time what he had built was a team that got swept in the playoffs. And there were still people excusing him for a variety of half-assed reasons. It's 8 months later and the excuses keep coming. "If you liked Olshey's 6th year team, you'll really love his 10th year team...be fucking patient and shut your mouth"
Whitsitt wasn't perfect; he didn't pay attention to fit or chemistry. And just like Olshey, he had some favorite players, like Detlef Schrempf. But he was able to get high end talent and didn't confuse average talent for high end talent just because he drafted it. I wouldn't want Whitsitt or a Whitsitt-clone back, but I sure wish Portland had a GM that would spend more time taking the risks of going after high end talent, and less time servicing his own ego