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If the season ended today, the Cubs would host the Philadelphia Phillies in a best-of-three series at Wrigley Field for the right to play the Milwaukee Brewers in the National League Division Series. It's not the situation they'd hoped they might end up in when they made a series of big moves at the trade deadline, but all things considered, it would be a good outcome. It's also far from guaranteed to them. In fact, thanks to a 6-9 stretch in which they've lost series to three sub-.500 teams, they're only ahead of the Phillies via a tiebreaker, and they're considerably closer to falling out of the playoffs than to catching the Brewers and winning the NL Central.

Playoff odds always have to be considered in context. There are some things a projection system doesn't adequately account for, so the odds assigned to a given team by a site like FanGraphs or Baseball Prospectus are never gospel. Furthermore, not every fan base should be looking at the same set of playoff odds to determine how it's reasonable to feel about their team and its chances. The Cubs are a good example. Here's a chart showing their chances of making the playoffs over the course of this season, via FanGraphs.

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After their roaring 27-12 start, the team reached an early high-water mark of 91.2% likely to make the postseason. That figure sagged all the way into the 30s at the nadir of their ensuing rough patch, but they've made steady progress since then. After their additions at the trade deadline, they shot up to the high 90s in percentage chance to make it to October, and they're still there. However, merely making the playoffs was never this team's goal, and a backdoor entry and early exit would be a disappointing outcome for their season. Let's consider, instead, their chances of making it at least to the NLDS, where they lost to Milwaukee last fall.

How Likely Are the Cubs to Reach the Division Series?

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The team's best chances of getting back to where they ended last season still came way back in early May, when they were just under a 2-in-3 shot. Because the Brewers built a comfortable cushion in the division and never gave it back, even as the Cubs played much better from mid-June through mid-August, their odds of getting to the NLDS only rose into the low 60s. That was some comfort, at least. Thanks to the combination of their own struggles and the Brewers and Phillies getting hot lately, though, Chicago has dipped back to the wrong side of a coin flip to get to the Division Series—let alone to push to the NLCS or claim the pennant, as they'd surely hoped to be in position to do when they traded several prospects to upgrade the roster early this month.

Can the Cubs Still Win the NL Central?

It was always going to be different to meaningfully improve on a coin flip's chance to win the Wild Card Series, given the Phillies' ability to shorten the series with starters Zack Wheeler and Cristopher Sánchez and games with reliever Jhoan Duran. The surest way out of the Wild Card round is to win your division; the Cubs' chances of that have dwindled to nothing.

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That makes the final four weeks of the regular season an exercise in moving goalposts, without losing sight of the importance of putting the ball through them when the time comes. The Cubs can't win the division—not only mathematically, where the uphill climb is obvious, but because the Brewers are genuinely and significantly better than them. They can't afford to declare this season a failure, though, or even permit the possibility of that; too much has been invested in it. They should define success as a campaign in which they get back to the Division Series; that will mean winning another playoff series. Getting past the Brewers (or Dodgers, or the team from near Atlanta) can be viewed as a stretch goal, rather than as a must. 

Chicago has never run a payroll as high as the one they're running this year. They have several veteran players (Dansby Swanson and Alex Bregman foremost of them) who will never be better than they are right now, and who are under contract for significant sums for the rest of the decade. This winter brings massive roster uncertainty for them, and their farm system is weak. They pushed in a lot of chips on this season, and aren't in as strong a position as a large-market team emerging from a rebuild and enjoying a once-in-a-lifetime season from a superstar should be in, given that commitment. No matter. They just have to go defy the odds. It's time to win. If they don't, this fall should bring serious questions about the front office and its future.


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