It’s going to be a complicated final five days of the Cubs‘ 2026 season. To say nothing for what the playoffs might hold, just finishing the regular 162 games is going to take some machinations.

Not that the Cubs aren’t already accustomed to that; navigating the pitching injuries alone has been a puzzle to be solved since April. A successful season takes more than just playing well on the field, and the Cubs have done an effective job of working with what’s been thrown at them.

“What’s great about teams is you got your opponents in front of you and you try to beat them,” manager Craig Counsell said. “And then you also got all these circumstances in front of you that you got to beat throughout the course of the season. And I think one of the things that thus far we’ve done a good job of is whatever circumstances get thrown in front of this group, they’ve responded really well to it.”

The big picture story is who the Cubs’ first round opponent will be and where those games will be played Clinching their postseason spot is essentially a formality at this point, but with Tuesday’s 12-inning 8-2 loss to the Marlins, it will wait at least one more day.

In the meantime, there are a few things to keep an eye on in the last five games before the playoffs begin.

Number one, Alex Bregman. After the foul ball that struck him in the face in Cincinnati on Sunday, and especially after the initial pictures of the damage to his eye that he posted to Instagram, it was tough to imagine him in uniform again any time soon.

But the Bregman news has gotten more encouraging with each day since then. It was reported on Monday that he wouldn’t need surgery, and then when the team returned to Wrigley on Tuesday, Counsell and team president Jed Hoyer said that Bregman will not go on the injured list and might even play later this week.

Bregman was in the batting cage with a helmet on during batting practice before Tuesday’s game, and Hoyer said whether Bregman plays in the next five days will depend on how he feels as he starts moving around, doing things like running and playing the field.

“I think we have to let him go through the steps a little bit here. But it’s been it’s been great news so far,” he said.

Given Bregman’s second half — he has a 167 wRC+ since the All-Star break — getting him back for the playoffs would be a stroke of good fortune. If he is actually able to return before the regular season ends, that will come at a critical time for influencing the Cubs’ playoff seeding.

Also potentially impacting the Cubs’ postseason picture is the forecast for Boston this weekend. It’s tough to predict exactly how things will look, but the weather is expected to be bad enough that the league is already considering options for how to get those games in.

Because both the Cubs and Red Sox are playoff teams and their final records will matter for the wild card round, the option to not play one or two of the three-game weekend series is not on the table. Hoyer said playing next Monday, September 28, is the least desirable option, and he would not comment on the possibility of the two teams playing at an alternate site.

The most likely scenario is that the Cubs and Red Sox might have to play a doubleheader on Friday or Saturday with the third game on the opposite day, as the worst weather — as things currently stand — is anticipated Saturday evening and during the day on Sunday.

In the Cubs clubhouse, the sentiment is it’s best not to try and guess at what might happen in Boston over the weekend and keep the focus on what’s in front of them in the much shorter term.

“As we get closer, we’ll be able to make better decisions regarding that,” Counsell said. “But right now, the focus is just putting ourselves in position to be as good as we can for the next six games.

“[The league] has started conversations, but it’s weather, so the closer we can get to it. You’re going to get something wrong, and it’s going to change, but conversations have kicked off.”

Because of the expected bad weather, the Cubs may have to shuffle their pitching plans for the Boston series. With the wild card round starting the following Tuesday, they already have to be mindful of lining up their rotation for that three game series.

As a part of the pitching decisions, Counsell said Tuesday that Justin Steele is in consideration for a return during the Red Sox series. Steele hasn’t pitched in the majors since needing Tommy John surgery in April 2025. He has made four appearances for the Triple-A Iowa Cubs on a rehab assignment this month, and Steele was back in Chicago this week, set to throw a bullpen session at Wrigley on Wednesday.

“I’m really encouraged,” Counsell said. “He pitched really well in his last outing, and I think that’s most important. That’s a good feeling for him, just to pitch [and] to have success and feel like he threw the ball well.”

Obviously, one or two appearances out of the bullpen in the last few games of the season won’t give much of a sample size for the Cubs to judge whether Steele is an option for a postseason roster, but that’s not necessarily being ruled out.

“He’s going to be part of the discussion, but let’s get through [Wednesday], and we can keep observing and keep talking about it,” Hoyer said. “We have to be pretty fluid as we go into the weekend with the weather and competitiveness and lining everything up. So there’s a lot of variables in that conversation.”

The biggest win for Steele might just be getting back on a major league mound. In spring training, he was optimistic about a late May return, but a setback during his recovery in the spring has pushed him to at least the end of September.

The next five days will help set the stage for the playoffs, and by the time they’re done, a few things about the Cubs’ postseason will be much more clear.