(Several years ago Phil Mickelson was one down on 18 and needed to hole out from fairway to force a tie. He had his caddy go ahead and "attend" the stick even though he was hitting from a fair amount back in the fairway).
When reading the OP, I too immediately thought of Mickelson. Not because I know much, or follow, PGA contest, but I was involved in the same discussion on discord a while back. I had posted a few clips of long approaches I holed out and having pulled the pin, which I do on every shot to the green.
Someone replied to my videos saying something about how stupid it is that WGT allows you to pull the flag on shots from far away, and I went on to use "google" to obtain ammunition for my reply. I came across two instances where Mickelson had sent his caddie ahead to pull the flag.
Here is a link to one video (the Masters I think) he was 60 yards out and had caddie go pull the pin:
The other one I found was from 2011 Farmers Insurance Open (10th Hole, Par 5, Final Round, 3rd shot to the green-72 yards out).
TBH, my videos of pulled pin approaches are way better than Phils' (I made mine)....just sayin'