The 2026 Cubs & the Rarity of Contention
I hope the 2026 Chicago Cubs win the World Series.
This probably isn't very important seeing as I also wanted the Chicago Cubs to win the World Series in 2025, 2024, and every year before that until you reach 1998 --the first year I became aware of baseball in any kind of substantial way. But once I did, I retroactively wished that they had won the World Series in every year before that...all the way back to the fabled 1908, which may as well have been during the Enlightenment.
Will the 2026 Chicago Cubs win the World Series? Likely not, but only because no one team is significantly likely to do it. I suppose the Dodgers are an exception to this seeing as they have won the past two World Series, have a payroll somewhere in the $27 billion range --it's $576 million, but really, what's the difference?-- and have every projection putting them just under/over 100 wins, which is absurd seeing as most projections like ZiPS (96 wins) and PECOTA (104 wins, lol) are notoriously conservative by their nature.
But could the 2026 Chicago Cubs win the World Series? Yes. And not in the "hey, everybody's 0-0 at the start" kind of way. It's reasonable to call them one of the best eight or so teams in baseball. You might even be able to argue top five, but you'll probably have to see some proof on the field before going out on that particular limb.
What's bizarre is the chasm between how rare this actually is and how rare it feels like this is. It feels like it's not really all that uncommon. The actual says that since I started watching the Cubs in 1998, this is maybe the sixth time they have been considered a World Series contender prior to the season.
The 2004 Cubs were thought to have a shot. Coming off the 2003 National League Championship loss to the Marlins --thanks to Steve Bartman, Bernie Mac, Alex Gonzalez, Dusty Baker, or whichever villain you like best-- it was presumed that the encore version was going to finally get it done. They went 89-73 (ironically six games better than the 2003 team) but failed to make the playoffs thanks to a late-season collapse --losing 7 of their last 9 games, which was completely and utterly presumed to be exactly what the Cubs would do; what they would always do --choke. Blame the clubhouse drama, or the injuries, or a combination, but once things got going, they never looked like a championship team on the field.
Although there was unquestioned hype surrounding the 2007 team, that hype came from several free agent signings rather than a bonified shot to win it all. This was a team that was coming off a 66-96 season. The free agent spending spree of Alfonso Soriano (8 years, $136 million), Ted Lilly (4 years, $40 million), Jason Marquis (3 years, $21 million), and Mark DeRosa (3 years, $13 million), coupled with the arrival of grumpy, championship-winning Lou Piniella to manage the whole thing, signaled the Cubs were ready to compete, not that they were suddenly World Series favorites.
The '07 team went a pedestrian 85-77, which was enough to win the Central --those were the days. They were promptly dispatched by way of a first round sweep at the hands of the Arizona Diamondbacks. The 2008 Cubs were different. The expectations raised and the '08 team was mostly the advertised juggernaut all season, going 97-64. But again, they were immediately dispatched in the first round of the playoffs, this time by the Dodgers.
Like a more plausible version of the '07 energy, the momentum was there for the 2015 Cubs to be World Series contenders in the preseason --Joe Maddon and Jon Lester had both arrived (with a cascade of top prospects at Triple-A), signaling the end of the 2011-14 rebuild under Theo Epstein and Jed Hoyer-- but there was always the feeling, even as they moved through the season and started to look the part, that they were a year away. Like '07, there was excitement and hope, but they weren't contenders. At least not in March.
But 2016 was a different story. The Cubs team that looked the one capable of breaking the curse were the ones that did it -which is wild. Going into 2016, coming off a loss in the NLCS to the Mets (but also an intense Division Series win against the rival Cardinals), the Cubs added Jason Heyward and Ben Zobrist. That roster looked monstrous and it was exactly that. The Cubs went 103-58 and you know the rest.
The Cubs were deemed World Series contenders in 2017 when they were defending their title, which is to say mostly by default. They battled to 92-70, won the Central again, beat the Nationals in the Division Series, and then got annihilated by the Dodgers in the NLCS --something that even at the time people expected. As the Cubs battled the Nationals in the decisive Game 5, the jokes were clear: These two teams were playing for the right to get kicked in the throat by the Dodgers. And that's what happened. See you later.
There were some rumblings in 2018 about being a contender, but they were mostly echoes of 2016 --how can a team that has just gone to the NLCS three straight years and won the World Series in the middle of those three years not be considered a contender?
They ended as one of the most suspicious 95-win teams you can imagine. Across the final month-plus of the season, the offense collapsed, sporting a .663 team OPS throughout September with peripheral stats that legitimized the putrid performance. By the time they limped into the Wildcard Game against the Rockies, they predictably scored one run in a 13-inning, 2-1 loss. Season over.
So, in my 28 years of active Cubs fandom, the Cubs have been World Series contenders at the beginning of the season six times --2004, 2008, 2016, 2017, 2018, and 2026. About 21% of the time, the Cubs are presumed to be good enough to maybe make a World Series run. How that compares to other teams --I don't know. Certainly not the worst, but certainly not the best.
Yet, it doesn't feel that rare. Even though it only happens 21% of time. Even though it hasn't been plausible since 2018. Even though we can see factually the rarity of the situation. I promise you the percentage drops lower if you start adding years before 1998. The Cubs just were never good. When they were, those teams still get talked about as if they were dynastic (1989, 1984, 1969). The '84 and '89 teams lost in the NL Championship; the '69 team didn't even make the playoffs because of a brutal, black-cat-curse-infused September collapse (and a "Miracle Mets" run). That's how bad the Cubs were --teams that looked like they might (and didn't) make the playoffs were about as good as it got for decades.
This conflicting duality is likely explained by recency bias. Though the Cubs have only been pre-season contenders 6/28 times in my fandom, they have been 4/10 times in the last decade --almost doubling the usual rate. But recency bias will only explain why there is a gap between the reality and the feeling, but it doesn't erase how legitimately rare this preseason contention actually is. Which is a reminder, I suppose, to enjoy it while it lasts.
The current state of the Dodgers is a major wrench in this. Because of their grotesque amount of money, a roster so good that saying they're "loaded" doesn't even come close to encapsulating how good they actually are, and that through this they still manage to have a top-3 farm system, it feels like everyone is playing for second. Add in their back-to-back World Series wins --the first time since the Yankees in 1999-2000-- and it doesn't feel like this dominance is something that is going to happen, but something that is already happening.
Were it not for rarity of the Dodgers situation --this is different than even the mightiest financial years from the Yankees-- the excitement around the Cubs contender status would be a lot louder.
The narrative arc of this Cubs team is also harder to see. When Epstein/Hoyer took over in 2011, there was a clear vision: We are going to tear this down to the studs, flip assets for years, add prospect capital, and then, in about five years, strike.
That vision rapidly came into focus. You could look at the Cubs at any time and know exactly what phase of The Plan they were in. When they were bottoming out in 2012-2013 (101 and 96 losses, respectively), you saw them sign and flip veterans, you saw them start amassing the prospects, and, most importantly, in the middle of 2014, you saw the switch flip. Though they went 73-89, they went 28-27 in August and September.
And then came the parade of prospects, the Hall of Fame manager, and the big free agent signings in 2015. The contention window opened as the prospects were called up and really, really didn't suck. They weren't contenders in March, but by September they absolutely were. And they remained so until 2018.
Compare that to a much more uneven reign of Jed Hoyer. The Cubs are, seemingly from the outside, much more conservative. They won a bastardized 2020 division thanks to COVID (34-26), but were swept in the first round; they blew up the World Series core in 2021 (71-91), were bad in 2022 (74-88), were meh in 2023 (83-79), and were better in 2024 but stumbled down the stretch and finished with the same 83-79 record as the previous year. They finally took a step forward in 2025, but even then won 92 games and lost the division by five games to the Brewers.
All of that is to say that the trajectory of the Cubs under Jed Hoyer is much more difficult to measure because they've done it so methodically --to the point of "hey, I only have so many more years to live, let's go." And now on the cusp of their first real season of viable contention under Hoyer's leadership, it's much harder to peg them for the long-term success Theo Epstein always talked about. It's a good team, but not one that has unassailable bones like 2016.
But here we are. On the cusp of another baseball season. And the Cubs have a chance to raise another banner if, like every champion before them, a great many things go right. And as ever, I hope that happens.