You gotta work it man. I know, easier said than done. You don't want to beg, but just put yourself in the position where you're around the $100 tippers. Know what ball they play? Well, you just happened to come across a box for him. Not sure what connections you have, but maybe you know someone who makes clubs. Or hey, I have an extra ticket to the US Open at Erin Hills. I assume some of the $100 tippers go to the bar after their round? You just happen to be there, and strike up a conversation. This way you're not begging, it will just naturally come up at some point, and if you get along with them of course they're going to request you to caddy for them. I agree, you have to grease that wheel. Is there always a designated line of who is next to go off? Can the person in charge change that ever? You could always tip him when you get the big guys! But the best way for sure is to get the big guys to request you. Hell, you should just approach one of them and ask him if he has a regular caddy. If he says no, tell him you'd like to be his regular. Tell him you're good, and you know this course. "I think if I consistently caddied for you, it would help your scorecard." Might be cheesy but I bet a lot of these guys like someone who has the guts to do that.