The man's a lunatic. I read that he hired some pickpockets to steal from his players during a club meal, then used it as a lesson that they should always be on the alert.
It's a bit of an extreme lesson. You tend to be on high alert in certain situations, such as when you are on public transport, or when you are carrying out a dangerous task, or if failure at your job would have serious consequences. Doesn't really apply to a relaxing meal in controlled surroundings.
Plus, where do you go if you want to hire some criminals? Do they have their own agency?