Quantifying Hope: Cubs Enter White Sox Series with 67% Postseason Odds

The Cubs haven’t been playing their best baseball over the last week and a half or so, dropping two of three to both the Giants and Mets before failing to close out a sweep of the lowly Marlins. Now they face a team that would be the worst in baseball if not for the Rockies, who could challenge for the worst record of all time. Pat Hughes will undoubtedly say you can throw the records out the window when the Cubs and White Sox play, and that could be true.

For the sake of their early division lead, however, the Cubs need to take care of business this weekend. Even though the Cardinals don’t figure to have staying power far beyond their hot stretch of play, they’re only a game back heading out to play Missouri’s more beloved team. Despite their closeness in the standings, projection models still favor the Cubs heavily over their rivals from America’s Armpit, giving the North Siders 67% postseason odds while the Cards are less than half of that.

The rest of the division steps down almost geometrically from there, with the Brewers under 15%, the Reds at just over 6%, and the Pirates not even worthy of an integer. I saw something yesterday — it might have been my boy Jeff Passan talking to Pat McAfee — about how the Pirates should seriously entertain the idea of trading Paul Skenes now instead of in a few years, as has been inevitable from the time they drafted him. The haul they could get for an elite starter with four-plus years of control remaining would be unprecedented.

They are unlikely to do that because they can still milk one more year of pre-arbitration salary from him before still getting incredible value for at least his first arb season. Having already screwed up royally by failing to manipulate an extra year of service time while also losing out on draft pick compensation through MLB’s new prospect promotion incentives, I suspect the Pirates will fumble this in the end. Had they just called Skenes up immediately last season, they’d have gained an extra pick due to his Rookie of the Year win.

Instead, they called him up too late for him to qualify, then lost out on that year of service because winning RoY granted him a full year anyway. This isn’t the first time I’ve discussed that on these pages and it probably won’t be the last. It’s just such an egregiously stupid own-goal that I can’t help but call it out at every opportunity.

The bigger point is that the Pirates have failed in even the most modest attempt to build anything around Skenes. At least the Cubs have maintained a veil of plausible competitiveness in most of the seasons following their great run a decade ago. The Pirates averaged 93.33 wins per year from 2013-15, but have been over .500 in only one season since with back-to-back 100-loss seasons in 2021-22. They are wholly unserious.

Milwaukee appears destined for a sub-.500 record this season, and Cincinnati may have already burned up its annual early-season run. The Cubs can really put some distance between themselves and the rest of the division here in May, at which point the focus needs to be on adding pieces to compete with the rest of the NL’s best. Even though I’m reminded almost daily that they’ve already beaten many of those teams, winning in April is decidedly different from winning in October.