A baseball season is naturally segmented into parts like a series, a homestand, a month on the calendar, the first half vs. the second half, and so on. The Cubs crossed over the 81-game mark during their most recent road trip through St. Louis and Houston, meaning they are in the second half of the season in terms of games played, but the more traditionally recognized midpoint is the All-Star break, which remains about two weeks away.

Still, July brings with it a natural look forward toward the trade deadline, the second half of the season, and the playoffs. All three things loom large for the Cubs, and as they flipped the calendar to July with a 5-2 win over the Guardians that kicked off a weeklong homestand, the Cubs are also putting behind them what turned out to be a surprisingly grinding month.

The very beginning of the schedule looked like a widowmaker on paper, but the Cubs went 18-9 through late March/early April. They went 18-9 again in May. And then came June. The Cubs scuffled through the month, going 13-13 while fighting to maintain a division lead that kept narrowing as the Brewers, Cardinals, and Reds all climbed to overall records over .500. All that said, as June ended, the Cubs were still 14 games above .500, no matter what the month looked like.

“We’ve earned that record,” manager Craig Counsell said. “It doesn’t promise us anything forward. We’ve shown the ability to play good baseball. We’re confident we can play good baseball.”

Given the injuries to key members of the starting staff — Justin Steele and Shota Imanaga — it is worth considering that the worst thing that has come out of those injuries thus far is that 13-13 month of June. Now that Imanaga is back from his hamstring strain, the Cubs are well-positioned to post a winning record in July.

“I think we’ve done a great job,” Michael Busch said of the first three months of the season. “You know you’re going to go through a little rough patch here and there in a baseball season, but to manage those and to be able to bounce back is pretty key.

“Just seeing how many ways we can win games, that’s kind of what we are. We can win it defensively, offensively, we can win it on the mound, we can win it stealing bases. There’s so many ways we can win games.”

The question that gets bigger and bigger once July arrives is how to keep winning games. Teams in the Cubs’ position start looking to shore things up this time of year. Even with Imanaga back in the rotation, the Cubs need more starting pitching depth. Names like the Pirates’ Mitch Keller, the Marlins’ Sandy Alcantara, and the Diamondbacks’ Zac Gallen should be high on the list for the front office to consider at the deadline. Thanks to Steele and Imanaga’s absences, Cubs starters had a 23rd-ranked staff ERA in baseball (4.30) going into Tuesday night’s game.

Team president Jed Hoyer said Tuesday that the last four weeks before the deadline can still dictate a lot about a team’s moves — he pointed out how the Cubs themselves went from sellers to buyers in a matter of about a week and a half in July 2023 — but one of the obvious moves for him to make will be to acquire starting pitching.

“Obviously getting Shota back is a big help,” Hoyer said. “But you never have enough pitching depth, and we have had a lot of conversations with teams [and] we’ll continue to have a lot of conversations. These things ramp up and we take a little break at draft time, and then they ramp up again after that.

“So I think that when it comes to acquiring pitching depth, we’re on the lookout.”

There’s also the Cubs bullpen, which has been great this season, to the tune of a 3.27 ERA that ranked second in baseball before two scoreless innings on Tuesday. But Hoyer described a team’s reliever corps as a “living organism” that seems to always need tending, so to stand pat at the deadline and roll with the group they currently have is probably not going to happen.

“You’re always looking to fatten that area up,” Hoyer said. “In general, bullpens are a volatile area, but our guys have pitched really well. But it’s certainly an area you never want to look to as a set position. You can always look to add, if you can.”

Further down the list might be a right-handed bat, and maybe one who can play some third base. Matt Shaw has been better at the plate since his return from Triple-A Iowa, but he remains something of a hole in the lineup. Trading for starting pitching, bullpen help, and a bat would mean dipping pretty far into the Cubs’ prospect depth, and while Hoyer doesn’t necessarily let fan reaction guide his moves, there’s still the reality that many Cubs fans are still bristling at losing Cam Smith and Isaac Paredes in order to get what might be just one year of Kyle Tucker.

That said, 2025 has an air of 2016 to it, in that there is a feeling that the Cubs have a unique chance to not only make the playoffs but also to go on a deep run, but that’s only if they are aggressive enough at the trade deadline. Before Tuesday’s game, Fangraphs had their odds of making the playoffs at 87.6%, which is the lowest among current division leaders. Their projected chances of winning the World Series are at just a 5.7% chance, which is also lower than any other division leader, but also behind the Mets, who are second in the National League East.

That’s a reality Hoyer has to contend with as this month progresses. The Cubs are showing that they are well-equipped to keep winning games in the regular season, but his moves at the trade deadline on July 30 could be the difference between a ballclub that just makes the postseason and one that goes far in October.