The pick pocketing spree was just fine. If I was a young thief, I would have done it too. Andrew is just making a play to get the boys attention. The town would probably riot in a couple days if he did it. A way of getting his point across that the thieves guild does not run the city. He also loves the Gold Tooth as family.

If he was going to crack down, he would have let the good Captain loose. Then announced it. He is trying to let the boy know that the rules of the game have changed. He is saying, To quote Carmen, “Respect my ‘thoritay” as he controls those who control the sword. 

Odds are the thieves guild would probably be “do what you want and give us a cut.” Most of the leadership is/was older than Andrew. I could see him becoming a low level leader. His is a worry about where do I fit in. His generation is probably gone.