I am simply looking at this from the task that Jimmy is presented with. He is given a set of rules for drafting and told to enforce them for the entirety of the bike course. How is this accomplished when, to comprehensively enforce the rules from first rider to last rider, he requires visibility on near 100 miles of road concurrently? It's not possible. So, you have two choices:

1. be pragmatic, compromise, and do best to optimize where enforcement is targeted, at any time leaving large areas of the course unenforced and primed for cheating, or
2. look at how technology can help solve the problem comprehensively.

I'm just saying that if it were Google presented with Jimmy's challenge, they would go about it via option 2. And, like driverless cars, it would be an interesting, though far simpler, technical endeavor.

But, please, tell me more about culture.