To a degree worth arguing about? So what do you think the best team in baseball's (or the best roster you can reasonably construct, however you want to look at it) odds of winning are going into October? Assume HFA, as any best team in baseball would typically have. For amusement's sake yes! First off, it's obvious hyperbole to say "no matter how good." Do you really believe that? Where did you come up with 20%? Did you game by game chances to win? Based on what? Historical? Measuring team strength by season record? I'm not convinced it would be linear based on season's winning percentage, which seems to be the most common method. Lets say you wanted to be extremely generous and say the Cubs had a 66% chance against each opponent in each playoff series. That's pretty absurd, but lets say they were just that good. That works out to a ~28% chance of winning the World Series over the course of 3 playoff series. I don't think any team vs. another team in a short series has that high of an edge, especially against playoff teams.