Cubs Looking to Begin New Stretch of Annual Contention
Certain truisms in life stretch into the world of sports and beyond, one of which is that success breeds desire, and desire breeds sustainability. Following a 92-win season, the Cubs enter the 2026 campaign fresh off spending the second-highest amount of any team on free agency this past offseason. That means the expectations for this squad are higher than they’ve been in recent years. How do I know that? Because the boss man is feeling too.
In recent remarks to the media, chairman Tom Ricketts said the Cubs “obviously want to win the World Series every year.” This year’s team, plus a good handful of others to come, has a pretty great shot at doing just that.
With champagne splashing all over the tarp-covered home locker room inside the walls of a crisp Wrigley Field last October, the team and fans alike experienced the figurative and literal intoxicating rush of playoff success. Boasting one of their most loaded roster in years, the Cubs aim to leave nothing to the imagination as their quest for the franchise’s fourth World Series crown gets underway in a few short weeks. Even if the team looks slightly different after this season, their window has just barely cracked open.
Now, before we go any further, I know what you’re thinking: Tom, some pretty big players — including the hotly sought-after Nico Hoerner, Ian Happ, Seiya Suzuki, and hurler Jameson Taillon — are all free agents at the end of the season. That’s something the squad should be aware of, but not fret over, as it plots out how to maintain a high level of competitiveness into the future.
You can almost guarantee that this organization will not allow a mass exodus of its brightest stars at any point during the upcoming season or thereafter. Pete Crow-Armstrong has voluntarily tipped his hand, indicating that he wishes to remain a Cub for the long haul. Newcomers Alex Bregman and starting pitcher Edward Cabrera are inked to deals that keep them in Wrigleyville for the next three seasons at a minimum.
The excitement and anticipation at the outset of any new baseball season is enough to encourage some of us to sport a rosier shade of glasses than reality may allow. One thing about this 2026 Cubs team is clear, however: they have World Series expectations for a reason. Sifting through the best and brightest memories cemented from an enthralling 2025 campaign, one could lose themselves in hopes for an idealistic future of prosperity for this club. But this team isn’t built on hope; it’s built on results.
The cubs are returning players at key positions who still possess upside and championship muscle memory, and they’ve bolstered that with both steady leadership and dynamic tools. This club currently possesses the right mix to win right now, but it should be around a lot longer than that with the right moves.
