This post doesn't make it clear what your answer is. I want them to do as well as they possibly can every year. But in some years that could be 75 wins, 85 wins or 90 wins. Actually winning the world series is definitely the most important goal. But getting to the World Series would be a huge step. Clearly everybody is dying to see AC000000 (and maybe that's how it would look no matter if they won or lost in the world series). I've seen the Bears win a Super Bowl. So getting to one wasn't as big as seeing the Cubs get into one. Still, it was pretty darn cool to at least have the team make it after all these years. I would not take that bet with the Bears. They need to win it all now. But after so many horrible seasons, and all those disastrous playoff appearances, actually winning 2 series, and 8 total playoff games (including 2 theoretical WS wins) would be so much more than I've ever experienced as a Cubs fan. I would view it was the next step, and then take my chances the next year. Ideally this is a 95+ win team that racks up a division, NLDS, NLCS and WS win. But I'm not sure they are good enough for that, and division, NLDS, NLCS (plus a couple WS wins) would be pretty darn cool. My answer was to the "would you rather they miss the playoffs or break your heart" form of your question. I want them to go as far as possible every year and while I wouldn't be satisfied with a pennant, I wouldn't be as disappointed as if they missed the playoffs altogether. So, I'm with you.