My worst cycling-related experiences:
It was the end of the summer, I believe it was 1989. My dad asked me to zip over to my high school main office and drop off some tuition head-checks. Too lazy to walk a mile, I decided to take my brand new Maruishi (Tange tubing, Shimano 600 throughout, a beauty...) I was dressed in casual khakis, but decided to wear my new Detto Pietro racing shoes for the ride. I got to the school building, and figuring it would just take me a minute or so, I locked my bike with my Citadel lock, to a chain link fence. I come out of the office building a minute or two later... Gone was my bike, and a section of the gate. I ran into the building and asked one of the secretaries, who just walked in from a coffee break, if she had seen anyone suspicious outside. She answered, "No, but I did see two workmen politely asking me to clear the way so they could fix the gate". And I had to clickety clack my way home, realizing that I just blew all the money I received as Bar Mitzva presents... and wore down my new cleats. In those days, only professional or die-hard cyclists wore cleated shoes, or knew what the awkward looking footwear was all about, and I was accosted by amused looks, and side-long glances, on my mile-long trek.
A few years later, I was pulled off another expensive bike at gun point.
At least the criminals in my neighborhood have good taste...