I think this has more to do with baseball as a sport than it does anything else. But perhaps you're right....if you are I think the place to look would be at the bottom of the league. How often are some of the teams with the poorest financial situations, outmatched badly by their competitors, and without the resources to compete.....landing in the bottom? I wish I had the time to research that right now (I'll try later) but my sense is that these teams that pop up for the World Series are individual anomalies that belie the fact that they were stuck in a tar pit for years prior.
Yeah, KC is in that mix, but that was after 25 years of putridness. Tampa appears to be the exception that proves the rule: money buys less margin for error, quicker turnaround times, and better odds of sustainability. Baseball's current financial landscape doesn't prevent you from building a winner, but it's like having a mile race with someone who gets to use a scooter on flat ground and you're hiking up a mountain with a 70 pound suitcase.