@Hydde Chiesa is not an RB and is not a defensive wing player, he can hustle alot and pressure/recover possession with grinta, but dont expect him to be someone he is not, atleast full time. He is first and foremost an attacking winger with really high motor. He can do the role Cuadrado was doing in the Samp game, because it seemed to be an RM role with primarily attacking/keeping width tasks. But Chiesa is too good of an offensive player to think he is a candidate natural fullback/wingback. He can do a serviceable job there, and overally rotate everywhere except CM in the midfield and attack, but dont think he plays as far down the wing as Cuadrado does in that wing. But he might suit what Pirlo wants from his 3-4-3 well, super direct and aggressive footie that attacks in waves. Atleast based on first game.
My eyes tells me this is a limited brainless player who wouldnt suddenly improve because you add defensive tasks to his plate /even if wingback is a simple/straight forward role). Plus I seen him in Viola and Azzurri in this role, was just average, nothing out of the norm there. And thats back when he was better as a player, he has regressed alot. Plus he is severely left footed player who has the instinct to allways cut like its hard coded into his program, him getting stuck in sitautions and not being able to drive in as well will be a struggle for him compared to what he is used to. He can be emergency backup at times there, but to call him a solution for this role? Thats reaching, I'm not sure what its based on?
I truly hope he would prove me wrong and he is a success there, heck anywhere in the pitch, if he can be good, use him there. But he has been useless 2 years straight despite being a skilled enough player, but too low of football IQ to use the tools he has.