Every season has its narratives or milestones or memorable moments (both good and bad), but I think it’s fair to say the 2026 Chicago Cubs have been ESPECIALLY insane. And I think it’s even more fair to say the craziest stuff hasn’t even happened yet. After all, we’ve still got six head-to-head matchups against the Brewers (plus the postseason) awaiting.
But here on September 1, after a night like THAT closed out the month of August, I thought we could come up for air and take one quick look back at what has been a truly absurd season featuring two ten-game winning streaks, a ten-game losing streak, a billion trades, an injured ace, a handful of top prospects traded, record-setting seasons at the individual and franchise level, an MVP race, and so much more.
I’m obviously not going to hit on everything, and the timelines here are just loosely placed, but here are the moments that have stood out to me (broadly speaking) this year.
The Offseason
Cubs Convention reunites the 2016 World Series team Cubs acquire Edward Cabrera Cubs sign Alex BregmanThe Cubs had a very busy offseason, including spending real money on the bullpen for the first time in Jed Hoyer’s tenure as President of Baseball Operations (not that it’s worked out all too well …). But the two big moves that stood out? Trading for Edward Cabrera and signing Alex Bregman.
The former required the Cubs to part with Owen Caissie, one of their top prospects, and the latter required the Cubs to spend (and defer) more money than they usually do on free agents. Cabrera’s first season has not been great so far, but Bregman’s second half has been one to remember. Either way, it was a very big, very exciting offseason for a team with World Series aspirations.
The Alex Bregman signing was particularly memorable, as the news dropped right in the middle of the Bears’ gigantic comeback against the Packers on January 10:
Third baseman Alex Bregman and the Chicago Cubs are in agreement on a five-year, $175 million contract, sources tell ESPN. One year after their failed pursuit of Bregman in free agency, the Cubs land one of the biggest bats of the winter.
— Jeff Passan (@JeffPassan) January 11, 2026Also, the 2026 Cubs Convention featured a reunion of the World Series team on the tenth anniversary of the Cubs’ first championship in 108 years. This would be the first of a few former team assemblies this year.
March
Justin Steele gets cleared for activity (LOL … how naive we were) Daniel Palencia closes out the World Baseball Classic (LOL … how naive we were) Seiya Suzuki gets injured in the World Baseball Classic The Pete Crow-Armstrong extension drops Robot umpires make their debut The Nico Hoerner extension dropsEven though there were only a few regular season games, it was a busy month of March for the Cubs organization. We briefly thought Justin Steele’s return could be so early in the season the Cubs wouldn’t even need to put him on the IL. We celebrated the experience Daniel Palencia got as the closer for Team Venezuela. We watched as Suzuki injured his knee sliding into second base, with the season flashing before our eyes (do you even remember that?).
And, of course, there were not one, but TWO awesome extensions to cap off the “offseason,” one for Pete Crow-Armstrong (thank GOD) and one for Nico Hoerner.
As a reminder, PCA’s extension looks like this: Six years, $115 million. And it kicks in after the 2026 season and buys out two free-agent years (his age 29 and 30 seasons). That extension quickly went from “nice idea” to “thank god they did this” to “… man they really should’ve tried to extend him even longer!” Either way, it was a good move, because it’ll now undoubtedly save the Cubs some money through arbitration *and* it bought them two years of free agency at what will probably be well below market value.
The Nico Hoerner extension (six years, $144 million) was also a great move, as it prevented the Cubs middle infielder from hitting free agency two months from now. And although the first half of his season wasn’t very good, he has been absolutely excellent at the plate in the second half (.333/.355/.444; 122 wRC+) while covering at short for Dansby Swanson.
April
Cade Horton leaves with the trainer, gets surgery First ten-game winning streak Justin Steele’s setback 3 walk-off winsCade Horton came into this Cubs season as maybe the most important player on the team. Or, at least, the player with the most upside outside of Pete Crow-Armstrong. His first start was fantastic (6.1 IP, 4H, 2ER, 1BB, 4K) … and he didn’t make it out of the second inning of his second start.
This was the first, but most significant, of what was about to be an ONSLAUGHT of pitcher injuries that have more or less defined the Cubs 2026 season. Cade Horton, of course, went on to have Tommy John surgery and will miss most of the 2027 season as well.
The Cubs did have three walk-off wins in April plus their first ten-game winning streak. But the month ended on a sour note, as Justin Steele suffered a setback (flexor strain) that would ultimately keep him out until … checks notes … tomorrow, when he’s set to finally begin a rehab assignment.
May
Matthew Boyd knee surgery Second ten-game winning streak Ben Brown becomes a borderline ace PCA yells at the White Sox fan The offense falls apart Ten-game losing streak 3 walk-off wins in a rowThe hits kept coming in May, with many more pitcher injuries, including a second stint on the Injured List for Matthew Boyd, who underwent knee surgery.
But all those injuries also opened up the door for Ben Brown (and his new sinker) to emerge as a legitimate front-end starting pitching option for the Cubs. That obviously hasn’t played out the way we imagined because of his neck, but let’s not get ahead of ourselves.
Before things turned south this month, the Cubs had their second ten-game winning streak of the season, including THREE STRAIGHT walk-off wins against the Reds.
Unfortunately, shortly thereafter, the Cubs had a ten-game losing streak, PCA got into it with that White Sox fan at Rate Field, and the offense absolutely fell apart.
A photo of Pete Crow-Armstrong exchanging words with a White Sox fan, who says she was at the game for her engagement party(via @girlfieri__) t.co/8FrBUEM4M6 pic.twitter.com/RZcMHOVo6M
— Talkin' Baseball (@TalkinBaseball_) May 17, 2026Rock bottom didn’t happen until the beginning of June, but this was the start of what felt like the end of the season. Little did we know, June was the start of something better.
June
Cubs hit rock bottom (.500 record) PCA hits for the Cycle Cubs trade for David Peterson Dansby Swanson goes nuclear with homers and RBI June 24: Cabrera carted off, Ben Brown hurt, Dansby grand slam 4 walk-off winsBefore it got better, it got worse.
On June 10, the Cubs hit rock bottom, touching back down to .500 for the first time since mid-April. And if you remember back, they weren’t just losing a lot of games; they were losing a lot of games to really, REALLY bad teams (Athletics, Giants, Rockies, and so on).
But things started to turn around pretty quickly.
On June 15, Pete Crow-Armstrong hit for the cycle (and immediately got picked off), his first of many feats this year. Shortly thereafter, Dansby Swanson, who had been having a miserable season offensively, absolutely exploded at the plate. You might remember the homers most (including his 3-homer game early in July), but arguably the crazier accomplishment was his 26 RBI in ten games.
The 24 hours from late June 23 through June 24 were particularly wild.
In case you forgot, that’s when Edward Cabrera needed to be carted off the field, Craig Counsell was ejected after the most absurd, nonsensical call you’ve ever seen, Ben Brown re-injured his neck, the Cubs acquired Bryse Wilson, the team played a doubleheader against the Mets, Swanson had three more homers (in the middle of his insane stretch), and finally, the Cubs acquired David Peterson.
That last one proved to be especially critical, as the Cubs immediately turned Peterson’s season around.
But that wasn’t all for June. For the second time of the season, Daniel Palencia and Phil Maton hit the Injured List, joining Jameson Taillon, Edward Cabrera, Hoby Milner (whose appendix burst), and Ethan Roberts, who also hit the IL that month.
Oh, this is also when Matt Shaw was activated off the IL for the first time … and then hit the IL for a second time.
July
8-HR game/Swanson’s 3-HR game Champions Gate public reveal Bruce Levine’s “Twinkle Dee and Twinkle Dumb” post (Theo Epstein wearing the Twinkle Dee/Dumb shirt) Jameson Taillon DFA PCA Player of the MonthRelatively speaking, July was calmer than June. But there were still a lot of big moments.
On July 1, Dansby Swanson had his 3-homer game the same day the Cubs tied their franchise record with eight homers in one game (a record they beat just yesterday with nine home runs against the Brewers).
The Cubs also revealed their World-Series-memorializing “Champions Gate,” with the entire World Series team reuniting for the second time.
Introducing Champions Gate. Created as a tribute to the Chicago Cubs’ World Series championships, the monument honors the players and managers behind the franchise’s greatest achievements. While commemorating the historic titles of 1907, 1908 and 2016, Champions Gate also… pic.twitter.com/0199lntI8W
— Chicago Cubs (@Cubs) June 22, 2026Things got a little more serious after that, when Jed Hoyer designated Jameson Taillon for assignment, setting the tone for what this season is/was meant to be. Taillon had been a big part of the team in the past and was making a lot of money (to say nothing of how well-liked he was in the clubhouse). But the persistent onslaught of homers, slowed only by his time on the IL, became too much to handle. Finally, the Cubs moved on (in no small part because of how good David Peterson had been). And that was that.
Pete Crow-Armstrong was also the NL Player of the Month in July, slashing .278/.400/.611 (172 wRC+) with six home runs and six stolen bases.
And what’s funny is that month doesn’t hold a candle to his August: .280/.366/.703 (185 wRC+) with 14 HRs and six stolen bases.
August
Trade deadline: Gausman, Holmes, Zeferjahn, Taylor BN implodes; I make the wrong report on Reid Detmers Cubs sweep the Dodgers Bregman’s first 3-homer night Dansby gets hurt PCA leadoff and walk-off homer to hit 30/30 Ben Brown’s setback and potentially done for the year? 150th anniversary weekend PCA hits three homers, Sosa called it Bregman’s second 3-homer game 3 walk-off wins Cubs 9-homer game and 62 homers in the monthAnd then August was perhaps the busiest and craziest month of all.
Before the bell rang at the trade deadline, I incorrectly reported that the Cubs had acquired Reid Detmers *and* this site broke down … like completely … on the busiest and most important day of the year. That sucked. But Jed Hoyer salvaged the weekend/deadline by acquiring Clay Holmes, Kevin Gausman, Tyrone Taylor, and Ryan Zeferjahn, among others.
Those trades cost the Cubs some promising young players and prospects, including, most notably, Moises Ballesteros and Jefferson Rojas.
Also salvaging the week, the Cubs swept the Dodgers in three games at Wrigley Field.
Not long after that, Alex Bregman had his first 3-homer game of the month (yeah, his first), Dansby Swanson hurt his oblique, Pete Crow-Armstrong started and ended a game with a home run to notch his second 30/30 season in as many years, and that’s just halfway through!
In the second half of August, we learned about Ben Brown’s setback, just as he was about to embark on a rehab assignment. Then, the Cubs did their 150th anniversary celebration, which included Sammy Sosa telling PCA he was going to hit three home runs in the game … which he did.
THEN, last night, Alex Bregman had his second 3-homer game of the year, as the Cubs set a new franchise record with nine homers in a single game and an NL record with 62 homers in a single month.
Indeed, while there were a lot of absolutely brilliant offensive performances for the Cubs in August, Alex Bregman and Pete Crow-Armstrong stand out among the best:
Pete Crow-Armstrong & Alex Bregman of the @Cubs are the first MLB teammate duo to combine for:25+ home runs25+ walks50+ RBI50+ runs scored…in a calendar month since Roger Maris & Mickey Mantle in July 1961. pic.twitter.com/631BKaEvGa
— OptaSTATS (@OptaSTATS) September 1, 2026What Else Happened?
And there are so, so many things I didn’t even begin to cover.
Seiya Suzuki is having his best overall year both offensively (139 wRC+) and defensively. He has already earned a career-best 4.2 WAR with several weeks to go. Pedro Ramirez has emerged as a legitimate weapon with positional versatility, slashing .285/.347/.436 (117 wRC+) in his rookie season, while playing all over the infield. Jacob Webb emerged as a savior for the bullpen, rising to the job of closer when the Cubs needed ANYONE to take it over. Edward Cabrera’s 100th stint on the Injured List resulted in a plan to move into the bullpen for the rest of the season. Phil Maton was a huge bust in his first season in Chicago. Hunter Harvey has barely been seen. Tyler Austin hasn’t been seen at all. Shelby Miller might be a thing. Etc. Generally speaking, Pete Crow-Armstrong has emerged as the NL MVP front-runner, while delivering one of the single best individual seasons in 150 years of Cubs baseball.What Might Happen Next?
And there’s still a month to go!
So what might happen next? On an individual level …
Pete Crow-Armstrong is just two homers and eight stolen bases away from a 40/40 campaign, to say nothing of his first MVP award. Ian Happ is two homers away from becoming a member of the Cubs top-10 all-time home run leaderboard. Alex Bregman has somehow given himself a very real shot at reaching 30 homers, after hitting just NINE before the All-Star break. Seiya Suzuki has a shot to be nominated for a Gold Glove award out in right field. Justin Steele is a day away from beginning his rehab assignment and potentially making it back to the team. Edward Cabrera could return in relief. To what level of success, no one knows.And I could go on.
I didn’t even mention the fact that the Cubs have BY FAR the best all-around defense we’ve maybe ever seen and arguably the top offense in baseball.
Plus, they simply still have a ton of work to do. There are six more games against the Brewers, all while the Cubs are battling to keep hold of the top Wild Card slot to maintain home-field advantage in the playoffs. And, of course, there’ll be whatever happens in the postseason, which will be what ultimately defines the year.
***
I’m sure I missed a ton (drop my blind spots in the comments below). But that just underscores how bonkers-nutso-crazy this season has been.
And if all of this wasn’t enough, here’s a list of some of the outgoing free agents leaving us at the end of the year:
Shota Imanaga Kevin Gausman Ian Happ Seiya Suzuki Matthew Boyd Colin Rea (potentially) Hunter Harvey Aaron Civale Carson Kelly Caleb Thielbar Michael Conforto Tyler Austin David Peterson Tyrone Taylor Jameson Taillon (already gone)So soak it all in, Cubs fans, because this is not a normal season. It’s been a roller coaster AND THEN some. Let’s just hope we can find a way to end the year on a high. Last night was a good start. But there’s a lot of important baseball left to be played.
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