In my day there were very few roadmen that didn't get robbed at least once or twice, usually after making a good score. I won't name names but some of them are very well known players who had a moment of carelessness that cost them thousands! Some were followed out to their car, some to their hotel/motels and some right outside the poolroom. Personally I've had three attempts to rob me, and I was able to thwart all three. Lucky me. You can read about them in Pool Wars!
I used to leave my poolroom alone late at night after closing with several thou in my pocket. I always went out a different way (no routine), looked all around when exiting, took a different route to my car which I never parked in the same place. And yes, I was armed. My attitude at the time was if I had to give up the money I would, but I didn't want to get killed in the process. A couple of guys I know got killed, David Sizemore and Mike Carella.
I always left cash register money and even pay envelopes for my employees on Fridays when my day person opened up, and I always kept several thou in my safe there. Some smart guy scoped out where we kept the hidden key my employee used to open the office door in the morning (he hid in a corner and watched him open up). The thief snuck inside late at night, found the key and got into my office. He stole all the money out of the desk there and tried to unlock the safe but couldn't. I lost about $150 starter money for the cash register and over $800 in pay envelopes. There was $10,000 in the safe! He didn't get that. No more hidden key after that caper.