You can't talk about skyscrapers without talking about egos. Egos are very much a part of this business. And so the egos of two cities will inevitably clash when both have a culture of building these structures, like it or hate it.
It's like Megatron and Starscream. NYC is the "superior" city and Chicago will always be jealous. Not because there is anything wrong with Chicago. But because New York exists, and Chicago will ALWAYS have an ego and can't stand it.
It's just the way it is, and there's nothing wrong with that.