I'd personally be fine trading Richardson right now. I know he's playing well, but with 1.5 year left on his contract and shooting a little over his head right now his value will never be higher. And if you move him you play the young guys and hopefully one of them pops.
An expiring and a first would do it for me, I know its not a great look for this season but the c's need to make an asset play.
So, I would guess that Brad and Wyc are not looking at things this way. Consider the following:
1) J-Rich is playing well and probably the most important bench player currently. The team is just starting to hit its stride, so why break up a good thing? Also, maybe J-Rich is shooting better because the Jays are commanding attention? I haven't dug into the lineups to see if that's the case.
2) As far as playing the young guys, there's no indication that Ime is inclined to play them more (other than Grant).
3) Wyc is highly sensitive to how things look to fans and to players. He avoids 'not a great look' at all costs. I bet he highly values making the playoffs this season. It means more money AND sends a positive signal to both players and fans.