This, exactly. When I go to my local Portillo’s, ordering it “dry” still comes out soaked through the wrapper and bread slightly wet. If I order it “wet” or “dipped”, it’s basically an Italian beef soup in a soggy bread bowl.
When it comes to Italian beef, dry is very relative. No self-respecting Chicago Italian beef joint would ever serve it actually dry.
Also, stumbled across Luke’s Beef near the Sears Tower one time with my daughter. Possibly my favorite beef in the city. Place was full of cops and construction workers at lunch if you know what that means.