Because they both need space, e.g. Cuads play behind CR, cause CR always cuts inside, leaving Cuads one on one with defender. Both Cuads and Chiesa prefer to go wide, that’s not stackable.
i feel it would be a bit similar to what we had with Cancelo and Cuadrado playing simultaneously on that right side(altough we didn’t see it much as Cuads was injured for large chunks that season) so yeah, not very plausible as they’d both need space to roam around but that also still makes more sense to me as an option rather then benching Cuadrado and having Chiesa start as an RB/RWB with as many defensive tasks as on the offensive.... which he is largely unproven at, at least so far.
i think the only way Chiesa would work there and not look lost would be as an RM/RW if Danillo takes the RB or makeshift RCB role again and covers defensively just as he’s been doing on the left so far, but then again we would lose all the benefits that Cuadrado brings on the right while also losing the pace provided by Chiesa on the left, so again, all in all i feel this debate is pointless as i think the only way Cuads will ever be benched or pushed out from the formation we are playing now could be only related to an injury or suspension, that’s just how it stands rn.