Arsene Wenger has admitted there is always an element of risk with every new signing, particularly in relation to players' off-field behaviour.
The subject of how Premier League stars conduct themselves was thrown into the spotlight after Marlon King was jailed for 18 months for punching a woman in a nightclub.
Arsenal boss Wenger knows that there is only so much football clubs can do to keep tabs on their employees, and that the onus is on the individual to act in a responsible manner.
The Frenchman has revealed there have been times when he has been forced to gamble on transfer targets, particularly when other clubs were also involved in the race for their signature.
"You can't be in management as long as I have and not have that dilemma," he told the News of the World.
"I can give you a list of big names who I have faced this problem with. It is not always because they are bad guys, it can be because they are sometimes weak guys.
"They go out and they don't know where to stop. They do not master their life. In London it's impossible to keep track of a player's every move.
"Let's say you have a guy who drinks. He can drink at home, so how can you control that? He can have parties at home. Twenty years ago, the players went to the pub on a Tuesday and so on but now it's not so public.
"In ideal conditions no boss would make a mistake. It was always a race against time with opponents who may also want to sign the player.
"Sometimes you have to go blind and play poker."