The 2008 Cubs. They are going to make the playoffs everytime. The '06 Cards usually won't. The Cardinals made the playoffs and then won the world series, and you would take the 2008 Cubs, a team that failed to show up for even one inning and went home with the title "division winner"? That's some very strong kool aid there. Sure, with the benefit of hind sight. Unfortunately, teams can't be built that way. Without knowing the playoff result, the answer is simple: take the better regular season team every time