Heh-heh… 
NOT Hee-Hee, more like OOPS!!!
Need some context.
It was not unusual for US railroads to drift a caboose in order to reposition it.
I do believe you’d see someone on the platform to keep an eye on things and set the brake when necessary, however.
“Oh no, it got away AGAIN!”
“This time we’ll NEVER get it back!”
I had a couple of thoughts on this one.
First of all, when we were very much younger, my sister had a book entitled The Little Red Caboose That Ran Away. I still remember the train’s consist: “The car that was old, the car that was new, the car that was yellow, and the car that was blue.”
Second, I was on an unmanned caboose once as part of the furniture, as it were. I think it was my first ride on a GTW freight train to Durand from Muskegon. The westbound train would come in, and the same crew would take the eastbound out of town–over 130 miles each way–and it had to be done within the Hours of Service. So there was no dilly-dallying around at Muskegon.
This night the westbound train came into Muskegon. I greeted the conductor and brakeman–both old friends–as they got off the caboose. The yardmaster asked me, “You riding the caboose?” I was. “Better get on now!”.
The caboose was then cut away from the train by a yard engine, and kicked–I mean, really kicked!–the length of the yard where the head-end crew was waiting to tie it onto the end of the eastbound train. A very smooth operation–no soup was spilled on the conductor’s table, so to speak. Brakeman made the air hoses and I set up the markers (by that time just a reflectorized paddle). Carmen supervised the brake test once the power (two or three GP9/GP18s) was tied on. The train started pulling once the test was completed, and the hind-end crew boarded with bills, etc., at the yard office, at a speed which seemed pretty awesome to me at the time
Shows how free-rolling rail equipment is (video is only 0:40 long).
- PDN.
Maybe the brakeman was just going for lunch?