1) Richardson outperformed expectations from Spurs fans, but you make it seem like he just earned finals MVP. He might have shot better from 3 pt range (in a limited sample) than he did before (although he was shooting almost 40% when the Celtics traded him to us), but otherwise he didn't do anything he hadn't done before. Plus it's a one year rental we're talking about, since he's a FA in a year.
2) Consensus would have had us trading back if we wanted to grab Primo, yet the FO took him at 12. So just because "consensus" says the draft is flat, doesn't mean it is to Portland. And, more often than not, the team picking doesn't want to risk their preferred choice.
Also, the value of your offer is relative to what the others are offering, because even if they like 9+Richardson, they might like 10/11 + something else better, and I don't think it's that difficult for someone to put together a better offer than that.
So all in all, for that offer (9 + Richardson) to be successful, all of these would have to happen:
1) Portland not trading the pick away for an established big forward like Jerami Grant. Good chance they do.
2) Portland willing to risk their preferred choice by trading back. Who knows, but history says they may not.
3) Portland not receiving a better offer than that. Speculative, IMO they can do better than a 1 year rental of Richardson.
So yes, considering there's a good chance at least one of those premises don't hold true, I'd say it's quite unlikely that scenario could come to fruition.