The Tops floor manager was hired by the Chairmen to make their casino more approachable and guest friendly. The casino does this by having their floor manager give out special prizes like food and drink (and even a free hotel room), which entices Strip visitors to make use of the establishment (which, in reality, brings in more caps for the Chairmen).
The Tops floor manager will give the Courier food and drinks to encourage the player to gamble. The food and drinks will be given if the player wins some money. If you win too much and break the bank, the floor manager will ask the player to stop gambling at that establishment.
Big Winner, The Tops: After winning 2,500, 5,000, and 7,500 chips from gambling, the floor manager will reward you with special prizes. However after winning 10,000 chips, he bans you from playing at The Tops.