It's bad form to be biographical in such a thread, but being a Caddie and Caddiemaster in the Met area has been a lifelong trade.
Here are a few that come mind:
1. Golfer comes to ball stymied in the crotch of a tree, looks at the Caddie angrily and asks, "Is this the best you could do?"
Caddie answers, "You shoulda seen where it was."
2. In the 2002 Met Open at WFW my assigned pro starts the tournament off the famous Par 3 10th. He's a young asst. pro and in his first big local tournament; he's nervous as shit. A few of his members are watching him and his head pro is in the group behind us. He puts his 5 iron in the big right bunker, then blades his recovery dead out of bounds behind the green, drops into a hole, leaves two in the trap (who can blame him) out in "6" and three putts for a sextuple bogey "9." He looks to me for solace. I say...
"I'll bet your loose now"
3. Club members and their guests are very aware of the wagering that goes on between Caddies on the outcome of the matches. They don't, however, always know our sophisticated gambling rubric. Even though they can inure who's winning or losing, they frequently inquire as to how they are performing for your wager with your opposing Caddie, more than a little worried that perhaps you're cutthroat enough to sabotage them. One time, a great friend and long-time player of mine, Dick Dexter, dribbled his opening tee shot and saw me receiving money from the opposing Caddie. As he teed up and addressed his mulligan, he paused and looked over at me and asked with mock disgust, "Have things got so bad that now you abandon me before a shot is even played, you disloyal SOB?"
I answered, "No, you got it all wrong. He was betting you'd miss it altogether."
The tee box roared with laughter. When it quieted and DD addressed the mulligan, i waited until the last possible moment before he swung the club to say...
"You wanna know the odds on this one?"