What: “Oh yeah, I could take you down...” bronze trophy
When: During Year Two (Rubacava)
Where: High Rollers Club, Kitchen
The reason you gain access to the High Rollers Club is to get Chowchilla Charlie's cash briefcase. In order to do so, you have to gain access to the bottom floors of his establishment, and this is through the kitchen. When you first enter the kitchen, you'll see a large brute rolling a large keg towards an elevator, but you won't be able to call it up yourself after he leaves. Leave the room and come back (either at a later time, or pop out and come back in) and you should see the big guy sleeping in front of the elevator. This is Aitor, and you should try and talk to him about going down. Not specifically about going down the elevator, but being subtle will be the way you can go about getting this trophy, as he will instead suggest taking you out if it wasn't against the rules nowadays to hit customers.
Technically this is missable because you don't have to converse with Aitor at all. The solution to the puzzle in the kitchen involves Glottis instead.