[@Lotrix Molick]

As mentioned before, this man is drunk and it’s not unusual for guys like him to sell information to gangs and others for money, so sticking his nose into other peoples business or facilitating them to do stuff like gamble or whatever could potentially allow him to use that info to gain something in the future.

Given that he wants your guys help betting on a fight, he might also be inadvertently sizing you guys up concern your martial abilities. After all, only people really confident in their fisticuffs would wanna do weaponless, armorless scrapping. Of course winning some money is also as much an important factor as learning more about your guys abilities in the event he needs or wants to sell your information to people.

Lastly, while he doesn’t mention this, you can also infer that there’s something he’s not telling you about these Fisticuff brawls. It’s like he’s intentionally trying to undersell the actual difficulty of the bouts to make it sound less of a challenge and conversely, make the group think it’ll be easy money.