The sky will fall before a greedy fat cat corporate CEO will be elected as a public official - no matter what his track record in managing other people's money is.
Sure - I wasn't saying a corporate CEO would even be the right person to run a large city(though Bloomberg did pretty well relative to the expectations of a NYC mayor), but merely pointing out that businesses with operating budgets of a similar size are much choosier with who they put in charge.
In Baltimore, the democratic mayoral candidate is a shoe-in. So the Democratic mayoral primaries are actually the real election. And Scott bested his opponents in that competition with ~45,000 votes total.
So really only about 7% of the city(pop 620,000) voted for him, but that's just how the system works.