First: condolences to the rider's family and friends. Second: Condolences to the Chicago cycling community. I can only imagine how everyone involved is feeling right now.
I don't know the answer to the question. I just keep thinking that these events are supposed to be fun and it's no fun when people end up dead or seriously injured. I've done dumb ****. I went over the hood of a car and accept the responsibility for it. I should have seen it coming. The difference being, i was still breathing after the fact. I got lucky.
I have some mixed feelings on it all right now. We have an event coming up for which i will be working a checkpoint and I hope the emphasis is on fun more than competition...just be careful. I think with the increasing popularity it may be crucial to emphasize the fun more than the competition. I'm not a messenger and I never will be. Honestly I think that the whole thing has been watered down to the point where they can't even be considered "messenger races". These events are fun however, and I like to have fun with friends on bikes as long as nobody gets themselves killed.