It seems like the only points where the businessman excelled were things external to the city, i.e. where negotiating with other entities, which makes sense. I

It seems like the only points where the businessman excelled were things external to the city, i.e. where negotiating with other entities, which makes sense. I think the difference is that other parties approach a city as a business would, in an adversarial way; not necessarily in conflict, but with the clear knowledge that they are on opposing sides of a negotiation and neither is going to leave that table 100% happy. It's different when the Mayor is dealing with his City Council: they have to work and live together, and arguably should be working to the same goal; improving the city and making sure the City wins, not the Mayor or the Council. I think that's where the business politicians routinely stumble; they're used to being purely in a win/lose environment, where very interaction is inherently a "I'm going to screw someone or get screwed" situation, whereas a lot of politics really shouldn't be about that. The whole point of Civil Service is working for the benefit of the community, not yourself or your particular department. I also think this is why politicians suck at negotiating, because it's the opposite of what they're used to. In short, as with most things, the Truth is somewhere in the middle.