Exploring the Best- and Worst-Case Scenarios for the 2026 Chicago Cubs

[Jason Ross]

Image courtesy of © Rick Scuteri-Imagn Images

The close we get to Opening Day, the more projection systems help illuminate the path (and the season) ahead. PECOTA, for example, loves the Cubs in the 2026 season and thinks they have a 72.5% chance to win their division. However, within that single projection, PECOTA is telling you that the Cubs still have a 27.5% chance of not winning the division. and even a 13.4% chance of missing the playoffs altogether. This is just one system, others will have different outlooks on what the Cubs might be. So, what does the worst-case scenario for the 2026 Chicago Cubs look like? Conversely, what would the best-case scenario look like? Can the team win a World Series? Can they miss the playoffs entirely? Together, let's peer into the crystal ball.

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What does the worst-case scenario look like for the Cubs?
The 2026 season starts with hope, and an immediate boost thereto. The team has an early six-game homestand facing the lowly Nationals and Angels. Alas, cold weather in northern Illinois begins to derail the season right away, as Pete Crow-Armstrong pulls a hamstring in frigid Chicago temperatures, forcing rookie Kevin Alcántara into starting duty. The injury keeps the Cubs' center fielder out through May, as the team is cautious bringing him back, and Alcántara struggles to stay afloat. The team let at least one of Chas McCormick and Dylan Carlson leave at the end of spring training, and Justin Dean offers no relief. While Crow-Armstrong eventually returns, the hamstring injury hurts his defense and speed and the lefty has a down season. PECOTA's depth charts project Alcántara and Dean for a combined 385 plate appearances, and Crow-Armstrong for 595. In this scenario, those numbers get reversed.

Pitching-wise, the injury bug bites and the itch spreads. Matthew Boyd, fresh off the most productive season of his career, suffers from early-season arm fatigue, with his velocity dipping two ticks on the radar gun. In an effort to give the hurler some time to recover, Colin Rea jumps into the rotation but cannot reproduce his excellent 2025, either. The most tragic of the injuries happens a little later when Edward Cabrera feels something tugging in his elbow. An MRI reveals the worst-case scenario; it's Tommy John surgery for the newest Cub in the rotation. Before it's officially summer, the Cubs have lost their prized pitching addition. 

Hope begins to turn to frustration, as the much-anticipated return of Justin Steele takes longer than hoped. Steele, much like Boyd, shows diminished velocity in rehab starts in Iowa. After three or four starts, it's clear he's not entirely right yet, so the Cubs shut him down for a few extra weeks. The left-hander eventually returns to his pre-surgery velocity, but it's already July and the team is in a hole. 

Just up the interstate, Milwaukee has once again turned lemons into lemonade. Kyle Harrison, the once-ballyhooed prospect in San Francisco has added a little velocity and looks like a menace. The Brewers have also found a few more short kings to plug into their lineup and hold a four-game lead over the Cubs headed into the All-Star-Break; there's no stopping that machine. The upstart Pirates nip at the Cubs' heels as well. Jed Hoyer, hoping that the second half of the season will see a return to health for Crow-Armstrong, Boyd, and Steele, mostly sits the deadline out, choosing to add a few depth arms to the bullpen and half-heartedly upgrade the bench. 

Disaster strikes in mid-August, just as it seems like the Cubs are gaining momentum; Alex Bregman gets hit with a 95-mph fastball, breaking his wrist. While Matt Shaw has been an upgrade over 2025 nightmares Jon Berti and Vidal Bruján on the bench, his low-90s wRC+ doesn't include the second-half pop he had in 2025. Bouncing around the diamond has made his defense more suspect. He's not terrible, but the loss of the Cubs' newfound leader is profound. The Cubs have lost both of their biggest offseason additions. 

August and September begin a downward slide. While the team never truly flatlines, they are an unexciting, frustrating mess. For every 8-run outburst or defensive masterclass, they drop a 2-1 tilt to the Reds, or surrender six to the Pirates at home. Watching becomes a chore, but the team remains just close enough you can never stop watching. 

When October starts, the Cubs are left out of the playoffs. They finish third in the division, a handful of games behind both Milwaukee and Pittsburgh, with 81 wins. Injuries are mostly to blame, but Ballesteros was just okay; Shaw is unable to sustain gains made last year; Cade Horton's unable to beat his xFIP like he did in 2025; and many of the Cubs' young players will now enter a winter lockout with big questions hanging over them. Fans rage at the team for extending Hoyer last summer. Many wonder if the team will have the same resources in the upcoming offseason that they had this time, to retain players such as Nico Hoerner, Ian Happ and Seiya Suzuki. 

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What does the best case scenario for the Cubs look like? 
On the sunny side of Future Street, the Cubs exit spring training with no notable injuries. March 26 is unseasonably warm on the lakefront, with the thermometer reading a balmy 52° F. Alex Bregman, in his first home at-bat as a Cub, sends a ball 105 mph off the bat into the bleachers in left-center; the Wrigley faithful goes wild. The Cubs win a laugher, posting double-digit runs, and everything snowballs from there. In an inversion of last year's gauntlet of a start, the team faces only one playoff team from last season in their first 25 games (the aging, injury-depleted Philadelphia Phillies) and get off to an early NL Central lead.

As the temperature warms, the Cubs remain hot. Offensively, Ballesteros looks like the real deal; Shaw's bat looks like the guy who showed up post-All-Star break last year; and Bregman is the stick that stirs the coffee. Pitching-wise, the Cubs have a two-headed monster at the top of the rotation, as a healthy Cabrera and Horton have both come into their own. The pitching staff requires some Colin Rea interventions, as others in the rotation have small, annoying injuries, but nothing major. Justin Steele continues a smooth rehab, and by the end of May, he's on the cusp of a return. When Jameson Taillon pulls a quad fielding a ball, the lefty is called to the rescue and the Cubs add another excellent arm to the equation. 

When the All-Star break begins, the Cubs feature heavily in the festivities. Pete Crow-Armstrong and Bregman are selected via fan vote. Hoerner, Horton, Cabrera and Daniel Palencia all make the team, and it's clear to all that Michael Busch got snubbed. In the standings, the Cubs have the second-best record in the NL, while it's clear that at least for this year. the Brewers' pixie dust has run out. The North Siders have no major injuries come July, and the teams add a resurgent AJ Puk from a despondent Arizona Diamondbacks team to round out the bullpen. This team is cruising, and the vibes are great.

By September, the division is all but sewn up. The Brewers are in a second-place battle with the Pirates, but both teams are barely on the periphery of the Wild Card race. This allows the Cubs to rest players where they can and give valuable innings to top prospect Jaxon Wiggins. The team enters the playoffs rested, with the second seed in the NL. The Dodgers were good, but haven't been the dominating force many thought they were. The Cubs easily dispatch their first foe in the playoffs in just four games, setting up a date with the new Evil Empire out west. 

In what is a very hard-fought battle, the Cubs persevere and upset the two-time defending champs. No one player plays hero; but in a full-team effort, the visitors win a decisive Game 7, sending the team to the World Series. Surpassingly, an 83-win Baltimore team has gotten hot and found themselves between the Cubs and a championship. Sadly for the Orioles, they run out of steam. Chicago grounds the Birds in six games, winning the Series in front of their home crowd. Who cares about the impending lockout? The Cubs have climbed the mountain. Celebrate, rejoice and enjoy; we'll worry about the rest later.

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If your first thought is that these are extreme outcomes and are unlikely: of course they are! Remember, these are the "best" and the "worst" scenarios. For better and worse, both are plausible, however unlikely they may be. PECOTA gives the Cubs a 7% chance to win the World Series and a 17% chance to miss the playoffs outright; neither of these outcomes are impossible. The 2026 season will likely fall somewhere between the best and the worst cases. There will be injuries at inopportune times, to important players. There will be players who overachieve, and some who disappoint. This a very good baseball team, but likely not an elite one. Even in the best-case scenarios I can fathom. they're unlikely to be better over 162 games than the Dodgers.

But at the same time, even in the event of the worst-case tailspin, it's probably a team who will offer entertainment and hope until the bitter end. Milwaukee is a good team, probably better than PECOTA thinks they are, but they probably aren't a 95-win team this year, either. Even with injuries, the Cubs have a good roster and should be able to take a few lumps. 

This is going to be a fun year, but we'll have to wait a little longer to see just how fun it can be. 

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What are your predictions for the 2026 Cubs? Can the best case scenario of winning a Title happen? What's your worst case outcome? Sound off in the comments below!

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