The distribution on that scatter graph illustrates exactly what you're saying. Oakland is a prime example. They self impose poverty but manage to remain competitive because they have really smart people.
I get the flukiness of winning when you're not able to just toss cash around. But you also don't need to lose twenty years in a row either. And market size doesn't mean that a team like Pittsburgh can't gamble once in a while. What irks me is that there was never a long term plan to build around Cutch. It's easier to land some top talent when you draft so high every year but this is the same franchise that opted to avoid drafting a guy because he might cost them a few bucks and refused to go get talent that was available in trades. That behavior is inexcusable. Yet Pirate fans go running to the stadium and seem to be satisfied with "the experience" or how nice it is to sit in the stands at such a great park. I hear that so often and it blows my mind. Winning is maybe the third or fourth priority for the Pirates and somehow, they get a pass.
