The Cubs Second-Half Schedule and Playoff Path Is … Less Than Ideal ...Middle East

Given the outrageous number of injuries on the pitching side — plus their rival’s 100-win pace through the first half of the season — the 2026 Chicago Cubs are in a pretty good place here at the All-Star break.

They’re 12 games over .500, five games out of first in the NL Central, but alone at the top of the Wild Card standings. And like last year, that would ensure a home playoff series if things ended today. Not great, but like I said, under the circumstances, pretty resilient. With any good injury luck at all and a solid deadline, it’s not difficult to imagine them making a run from here.

But there is one unavoidable hurdle, and it bears calling out: their remaining strength of schedule.

From a raw won/loss standpoint, the Cubs have the third strongest schedule remaining in all of MLB (per Tankathon).

By contrast, the Milwaukee Brewers (.499 remaining) have the 17th toughest schedule remaining. Not ideal.

Power Rankings Guru goes about calculating remaining strength of schedule a little differently, ranking each opponent more subjectively and then averaging the average opponent rank the rest of the way. And while the Cubs still finish with the third toughest average opponent remaining, the Brewers do move up from 17th overall to 12th. So that’s a little encouraging. That is, if overtaking them in the NL Central is a dream onto which you’re still clinging.

To that end, the Cubs would need to make up five games over their remaining 66 contests, seven of which come head-to-head with the Brewers. So, yeah, it’s obviously possible. It’s just not statistically likely.

Indeed, FanGraphs projects the Cubs to win 34 more games (88-74) while the Brewers project to win 35 more games (94-68). In their scenario, the three division winners would be the Dodgers, Brewers, and Braves. Meanwhile, the three Wild Card teams would be the Phillies (one game better than the Cubs), Cubs, and Pirates.

That would result in the following NL Playoff Picture:

If this exact scenario were to play out, the Dodgers would host the winner of Cubs/Phillies while the Brewers would host the winner of Pirates/Braves. And let me tell you, this is just about the worst possible playoff path for the Cubs.

The good news is that the Cubs hold a tie-breaker over the Phillies, so if they were to tie things up by the time the final bell rings, at least they’d host that first series. But in either case, they’d then have to square up against the Dodgers in the NLDS.

And facing a rested Dodgers team (with home field advantage) after burning through a Wild Card series is … not great odds.

Needless to say, it would be swell if the Cubs could go ahead and overtake Milwaukee and earn that first-round bye. It’ll take them playing out of their minds the rest of the way – and even if that is the case, the Brewers hold their own fate in their hands – but it’s possible. The schedule is just one more hurdle they’ll have to overcome.

But we don’t have to leave it on a sour note.

Although the complete remaining schedule is quite tough, the Cubs actually have a pretty soft landing immediately out of the All-Star break.

They open things up with six games at home against the Twins (48-49) and Tigers (44-52) before hitting the road to face the Pirates (50-47) and Cardinals (50-45) before the trade deadline.

None of these teams are really awful (indeed, both the Twins and Tigers won 7 of their last 10 heading into the break). But they’re not the meat of the Cubs toughest stretch in the schedule, either. So, with any luck, they’ll go berserk out of the break, forcing Jed Hoyer to add significantly (at least on the pitching side) before the deadline.

Then, they can use those new players to tackle their really tough stretch thereafter, which begins with the Yankees and Dodgers (and, thanks to a rained-out makeup against Toronto), not many well-timed days off.

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