Illegal bookmaker's offices may not pay out winnings, and their sites can be blocked anytime.
The state of being legal or illegal of an online sportsbook depends on the player's region. Every gambling platform has a tendency to not pay your winnings out. This is most commonly observed on bookmaking businesses which are not regulated by any government. So if I were to be asked, I'll choose those regulated gambling sites over unregulated. There might be some exception sometimes though.