And the Pirates and Brewers probably won't have any good seasons during that time, either. So we tank 3 seasons, then split the division evenly with the Cardinals for the next six. Congratulations, Theo Epstein and Jed Hoyer, you just matched Jim Hendry's term. The Brewers are likely to decline. They have holes now, and purged their system over the past 4 years so they don't have the means to fill them. And let's dispense with predicting the number of potential playoff appearances and focus on the number of wins. If the Cubs win 90-95+ games each year for 6-7 consecutive years, that's success. If it leads to only 2-3 playoff appearances in that span, that'd still be a much more successful run than the one Hendry had. You can't control what other teams do, but if you're consistently winning 90+, you're getting it done. Hendry did not do this. First, I find it inconceivable that you are going to win 90+ games consistently for 6-7 years and only make the playoffs 2-3 times in that span. That being said, Theo and Co. were brought in to get us to the World Series and hopefully win it, so I would consider winning teams that don't make the playoffs as a failure after our "rebuild" is complete. It's not inconceivable, just highly unlikely. It was a bit of a counter to davell saying 6-7 playoff appearances. 90+ wins is a fairly successful season, but no guarantee of a playoff appearance. In such a scenario, under the current setup, I'd say a team would get at least 4-5 playoff berths. But a winning season would have to be considered more successful than an abysmal one 100% of the time. Baseball is a fickle sport, and playoff caliber seasons aren't always going to get you into the playoffs. What you have to aim for is to have playoff caliber seasons every year, to maximize your chances. This is where Hendry failed miserably, largely because his management didn't provide contingencies for when "plan A' failed. There were no backups waiting in the minors, everything was free agency, gambles, gambits and guesswork, especially after his trade ammo in the minors went dry.