Some of us here have done a lot of time as caddies. I've only done it once, in 2019, at Golspie. There was a group of eight Americans on a high dollar trip to Scotland. They had helicoptered from Askernish to the vicinity of Dornoch with the intention of playing 36 at RDGC. RDGC didn't have room on the tee sheet and they were steered to Golspie. This being short notice, Golspie was hard up for caddies and they asked if I would help out. I consented the night before without realizing quite how bad the weather was going to be. Aside from the fact it was about 5 degrees or less, raining, occasionally sleeting, I had the lone jerk in the group, and the painful part is he picked me because I was the lone fellow American caddying and he assumed he could understand me. I know his name and where he worked because I was able to look it up on LinkedIn after the round, but he shall remain anonymous..
Among his discretions: On the second hitting into a rainstorm being driven by approximately 25 mile an hour winds, he pulled his tee shot left of left into knee high rough. "Did you see it," he asks frantically.
"Not after it cleared the gorse."
"You're going to have to watch them closer."
Two holes later he misses a six foot putt to tie the hole, takes a vicious swipe at the ground and misses hitting turf by what looked like millimeters. As I was concentrating on keeping his equipment dry as possible I didn't notice he had thrown the putter into rough 40-50 feet right of the green.
This missing club wasn't called to my attention until he asked for the putter on the 5th green. "I laid it down by the green," he tells me. He's going to go and get it, but I tell him I'll go so they don't fall behind the first group or delay the group behind us.
I trudge back, as the following group if they have seen a putter. No, they say, so I continue to trudge backwards until I get to the 4th green, circumnavigate probably twice before widening my arm until I luckily catch a glimpse of shiny metal well away from the green in rough.
By the time I catch up to the group they are climbing the slope to the 7th. Also by this time he seems to realize our relationship has probably seen its best of times and he doesn't have anything to say beyond thanks.
Later on, I'm trying to help him read a tricky putt that goes the other way from what a cursory glance shows, but he's impatient and hits it on the wrong side of the hole and of course sees it stray even further off line.
On the 11th, Tinker's Camp, he hits a push slice well to right into the heather and tall grass separating the 9th and the 11th. I suggest he might want to hit a provisional, but he's certain we will find it as "It wasn't that bad."
After an exhaustive look by all of us caddies and players, he concludes that the group coming down the 9th, all of whom have hit their drives in the fairway, have stolen his ball. He goes on about this until the member of his group, some of whom work for him, grant him relief and allow him to drop a ball rather than go back to the tee.
From about 175 yards out he hits his best shot of the day and lands it on the green less than 20 feet from the hole. When he gets there he inquires/declares "I'm lying two, right?!" They deny him this status and the remark I recall is "That's a bit aggressive, B_____." Since then, I've thought of dodgy behavior or outright cheating as "a bit aggressive."
There are more failures to accept advice from me and the other caddies until we finish the round, soaked, sodden, drenched, and just this side of a chill. The agreed upon fee had been 80 GBP and to his credit he gave me 100 GBP. "Is that right, okay." I take the money, thank him, and resist the temptation to say "It's a good down payment."
Now those of us who have done this for a living have to have had horror stories relegating to a walk in the park, but here's your chance to pony up and dish the dirt.
One more by the way, this is architecturally related in that I discuss tricky putts.