General Discussion

...regarding what in his history would lead him to think he could run the largest city in the country.

I don't remember what his answer was, but I thought, mine would have been, "there's nothing that can prepare anyone for that."

I feel the same when it comes to governor of California. The only people that might even remotely have the experience to do so would be people that almost never would take the job (e.g., a former president). So, it comes down more to vision and the person's particular approach in general.