Is It Legal To Bet With A Bookie? If you’ve ever wanted to let some cash ride on the big game, you’ve probably wondered: is it legal to bet with a bookie? First and foremost, it is important clarify we are not referencing a local individual when we say “bookie”– we are referring to a licensed bookmaker. It is never advisable to use an unlicensed entity to place bets in the US. With that out of the way, it is legal to use a licensed bookie (bookmaker) to place wagers.