I was a young squire, or just a lad not yet pledged to the service of any knight. I'd gotten some money from somewhere, taken from my mom's purse or something, and snuck down to the arena. I faked my way in, faking my age and my standing, so they let me into the inner area. I went to the betting area to place a bet on one of the horses/knights in the competitions. Everything else was dirty and medeival but the betting area was very modern Vegas, smooth men in business suits and adding machines. They put my bet on a horse and I don't remember how it worked exactly, but it occured to me at the time that the betting was fixed-- that they made the games work exactly according to their odds so that nobody ever really won and they pretty much always got all they money. But at that point it was too late, my bet was placed.
So I wandered around the markets attached to the arena. Every step I took I was assailed with opportunities to spend money-- wenches would come up with trays of little appetizers and snacks. "It's just a pence, sir!" If I declined too many things in a row, a militia guardsman would appear and start intimidating me. "Are you to good for these fine peoples' wares?" It was clearly all a racket, that I was expected to spend whatever I didn't lose on the track. So I bought some stuff, a bag and a drum and I don't remember what else. Stuff I didn't need. And I was just about out of cash, so I thought I was done with the experience, ready to just watch the race (knowing full well that my horse was going to lose because of the rigged nature of it all)... but then the thieves started in. I was aware of stuff being taken from me by people I couldn't spot, and when I did catch people in the act and tried to take my stuff back, they were always able to make it look (again, to the nearby militia men who didn't see them steal from me) like I was starting a fight. I woke up having nothing at all, having to get the hell back out of the area market area without even watching my race, because I was not just broke but in trouble now as well.
But at the time, as I slipped back out, I was thinking to myself that if this were a movie or something, this was just a plot device to get me to the absolute bottom... so that it would be that much cooler when I came back and went all the way to the top at the end.